From e29b977e30f8cafcceeef15c5f6ee9a98d8fa73d Mon Sep 17 00:00:00 2001
From: shane <psh40963@naver.com>
Date: Sun, 2 Mar 2025 14:21:49 +0900
Subject: [PATCH 1/7] refactor: spring boot 3.3-> 3.4 & openai dependency

---
 build.gradle.kts                                     | 11 ++++++++++-
 .../dutypark/department/service/DepartmentService.kt |  3 +--
 .../dutypark/duty/repository/DutyRepository.kt       |  6 ++----
 src/main/resources/application.yml                   |  9 +++++++++
 .../department/service/DepartmentServiceTest.kt      | 12 +++---------
 .../dutypark/member/service/FriendServiceTest.kt     |  2 ++
 src/test/resources/application.yml                   | 10 ++++++++++
 7 files changed, 37 insertions(+), 16 deletions(-)

diff --git a/build.gradle.kts b/build.gradle.kts
index 45bf6134..67368ef8 100644
--- a/build.gradle.kts
+++ b/build.gradle.kts
@@ -3,7 +3,7 @@ plugins {
     kotlin("plugin.spring") version "2.1.10"
     kotlin("plugin.jpa") version "2.1.10"
     id("io.spring.dependency-management") version "1.1.7"
-    id("org.springframework.boot") version "3.3.5"
+    id("org.springframework.boot") version "3.4.3"
     id("org.asciidoctor.jvm.convert") version "3.3.2"
 }
 
@@ -20,6 +20,8 @@ repositories {
     mavenCentral()
 }
 
+extra["springAiVersion"] = "1.0.0-M6"
+
 val asciidoctorExt: Configuration by configurations.creating
 dependencies {
     // Kotlin
@@ -36,6 +38,7 @@ dependencies {
     implementation("org.springframework.boot:spring-boot-starter-actuator")
     implementation("org.springframework.boot:spring-boot-starter-webflux")
     runtimeOnly("io.netty:netty-resolver-dns-native-macos:4.1.93.Final:osx-aarch_64")
+    implementation("org.springframework.ai:spring-ai-openai-spring-boot-starter")
 
     // Monitoring
     implementation("io.micrometer:micrometer-registry-prometheus")
@@ -68,6 +71,12 @@ dependencies {
     runtimeOnly("io.jsonwebtoken:jjwt-jackson:0.11.5")
 }
 
+dependencyManagement {
+    imports {
+        mavenBom("org.springframework.ai:spring-ai-bom:${property("springAiVersion")}")
+    }
+}
+
 tasks.withType<Test> {
     useJUnitPlatform()
     failFast = true
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentService.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentService.kt
index 7430d2bf..858967cc 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentService.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentService.kt
@@ -68,9 +68,8 @@ class DepartmentService(
         if (department.members.isNotEmpty()) {
             throw IllegalStateException("Department has members")
         }
-        val dutyTypes = department.dutyTypes
-        dutyRepository.setDutyTypeNullIfDutyTypeIn(dutyTypes)
 
+        dutyRepository.deleteAllByDutyTypeIn(department.dutyTypes)
         departmentRepository.deleteById(id)
     }
 
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/duty/repository/DutyRepository.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/duty/repository/DutyRepository.kt
index e40c1213..5622d38f 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/duty/repository/DutyRepository.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/duty/repository/DutyRepository.kt
@@ -20,12 +20,10 @@ interface DutyRepository : JpaRepository<Duty, Long> {
     @Query("update Duty d set d.dutyType = null where d.dutyType = :dutyType")
     fun setDutyTypeNullIfDutyTypeIs(dutyType: DutyType)
 
-    @Modifying
-    @Query("update Duty d set d.dutyType = null where d.dutyType in :dutyTypes")
-    fun setDutyTypeNullIfDutyTypeIn(dutyTypes: Iterable<DutyType>)
-
     fun deleteDutiesByMemberAndDutyDateBetween(member: Member, start: LocalDate, end: LocalDate)
 
     fun findByDutyDateAndMemberIn(dutyDate: LocalDate, members: List<Member>): List<Duty>
 
+    fun deleteAllByDutyTypeIn(dutyTypes: List<DutyType>)
+
 }
diff --git a/src/main/resources/application.yml b/src/main/resources/application.yml
index 9fcdc9b6..5cbd33f3 100644
--- a/src/main/resources/application.yml
+++ b/src/main/resources/application.yml
@@ -21,6 +21,15 @@ spring:
   devtools:
     restart:
       enabled: false
+  ai:
+    openai:
+      api-key: "API_KEY_HERE"
+      chat:
+        base-url: "https://generativelanguage.googleapis.com/v1beta/openai/"
+        options:
+          model: "gemini-2.0-flash-lite"
+          temperature: 0.0
+        completions-path: "/chat/completions"
 
 server:
   port: 443
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentServiceTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentServiceTest.kt
index 2bfadc5d..876da3b5 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentServiceTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/department/service/DepartmentServiceTest.kt
@@ -123,7 +123,7 @@ class DepartmentServiceTest : DutyparkIntegrationTest() {
     }
 
     @Test
-    fun `When Department is deleted, All related duties will have null dutyType`(
+    fun `When Department is deleted, All related duties will removed`(
         @Autowired dutyService: DutyService,
         @Autowired dutyRepository: DutyRepository
     ) {
@@ -147,20 +147,14 @@ class DepartmentServiceTest : DutyparkIntegrationTest() {
 
         // When
         department.removeMember(member)
-        em.flush()
-
         service.delete(department.id!!)
 
         // Then
-        em.flush()
-        em.clear()
-
         assertThat(dutyTypeRepository.findById(dutyType1.id!!)).isEmpty
         assertThat(departmentRepository.findById(department.id!!)).isEmpty
 
-        val theDuty = dutyRepository.findById(duty?.id!!).orElseThrow()
-        assertThat(theDuty).isNotNull
-        assertThat(theDuty.dutyType).isNull()
+        val theDuty = dutyRepository.findById(duty?.id!!)
+        assertThat(theDuty).isEmpty
     }
 
     @Test
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/member/service/FriendServiceTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/member/service/FriendServiceTest.kt
index 17205f95..c243c443 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/member/service/FriendServiceTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/member/service/FriendServiceTest.kt
@@ -236,6 +236,8 @@ class FriendServiceTest : DutyparkIntegrationTest() {
         assertThat(friendService.findAllFriends(member2)).isEmpty()
 
         setFriend(TestData.member, TestData.member2)
+        em.flush()
+        em.clear()
 
         // When
         val friends = friendService.findAllFriends(member1)
diff --git a/src/test/resources/application.yml b/src/test/resources/application.yml
index 06bba3a8..082b888b 100644
--- a/src/test/resources/application.yml
+++ b/src/test/resources/application.yml
@@ -12,6 +12,16 @@ spring:
   flyway:
     enabled: false
 
+  ai:
+    openai:
+      api-key: "API_KEY_HERE"
+      chat:
+        base-url: "https://generativelanguage.googleapis.com/v1beta/openai/"
+        options:
+          model: "gemini-2.0-flash-lite"
+          temperature: 0.0
+        completions-path: "/chat/completions"
+
 decorator:
   datasource:
     p6spy:

From 412d2a4ee26be6ee26f0705541559d34c7200f37 Mon Sep 17 00:00:00 2001
From: shane <psh40963@naver.com>
Date: Sun, 2 Mar 2025 15:37:56 +0900
Subject: [PATCH 2/7] feat: ScheduleTimeExtractionService

---
 .../shanepark/dutypark/DutyparkApplication.kt | 10 +++
 .../domain/ScheduleTimeExtractionRequest.kt   |  9 +++
 .../domain/ScheduleTimeExtractionResponse.kt  |  9 +++
 .../service/ScheduleTimeExtractionService.kt  | 70 +++++++++++++++++++
 src/main/resources/application.yml            |  2 +-
 .../dutypark/DutyparkIntegrationTest.kt       |  6 +-
 .../tistory/shanepark/dutypark/TestUtils.kt   | 17 +++++
 .../ScheduleTimeExtractionServiceTest.kt      | 57 +++++++++++++++
 8 files changed, 174 insertions(+), 6 deletions(-)
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionResponse.kt
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionService.kt
 create mode 100644 src/test/kotlin/com/tistory/shanepark/dutypark/TestUtils.kt
 create mode 100644 src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt

diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/DutyparkApplication.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/DutyparkApplication.kt
index 85a7a171..b804e817 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/DutyparkApplication.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/DutyparkApplication.kt
@@ -1,10 +1,13 @@
 package com.tistory.shanepark.dutypark
 
+import com.fasterxml.jackson.databind.ObjectMapper
+import com.fasterxml.jackson.datatype.jsr310.JavaTimeModule
 import org.springframework.boot.autoconfigure.SpringBootApplication
 import org.springframework.boot.autoconfigure.security.servlet.UserDetailsServiceAutoConfiguration
 import org.springframework.boot.context.properties.ConfigurationPropertiesScan
 import org.springframework.boot.runApplication
 import org.springframework.cache.annotation.EnableCaching
+import org.springframework.context.annotation.Bean
 import org.springframework.data.jpa.repository.config.EnableJpaAuditing
 import org.springframework.scheduling.annotation.EnableScheduling
 
@@ -19,6 +22,13 @@ fun main(args: Array<String>) {
     runApplication<DutyparkApplication>(*args)
 }
 
+@Bean
+fun objectMapper(): ObjectMapper {
+    return ObjectMapper().apply {
+        registerModule(JavaTimeModule())
+    }
+}
+
 
 
 
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt
new file mode 100644
index 00000000..342641ad
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt
@@ -0,0 +1,9 @@
+package com.tistory.shanepark.dutypark.schedule.timeextract.domain
+
+import java.time.LocalDate
+
+data class ScheduleTimeExtractionRequest(
+    val date: LocalDate,
+    val content: String,
+) {
+}
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionResponse.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionResponse.kt
new file mode 100644
index 00000000..37d3885c
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionResponse.kt
@@ -0,0 +1,9 @@
+package com.tistory.shanepark.dutypark.schedule.timeextract.domain
+
+data class ScheduleTimeExtractionResponse(
+    val result: Boolean = false,
+    val hasTime: Boolean = false,
+    val dateTime: String? = null,
+    val content: String? = null,
+) {
+}
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionService.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionService.kt
new file mode 100644
index 00000000..739e3ea0
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionService.kt
@@ -0,0 +1,70 @@
+package com.tistory.shanepark.dutypark.schedule.timeextract.service
+
+import com.fasterxml.jackson.core.JsonProcessingException
+import com.fasterxml.jackson.databind.ObjectMapper
+import com.tistory.shanepark.dutypark.schedule.timeextract.domain.ScheduleTimeExtractionRequest
+import com.tistory.shanepark.dutypark.schedule.timeextract.domain.ScheduleTimeExtractionResponse
+import org.springframework.ai.chat.client.ChatClient
+import org.springframework.ai.chat.model.ChatModel
+
+class ScheduleTimeExtractionService(
+    chatModel: ChatModel,
+    private val objectMapper: ObjectMapper
+) {
+    private val chatClient = ChatClient.builder(chatModel).build()
+    private val log: org.slf4j.Logger = org.slf4j.LoggerFactory.getLogger(ScheduleTimeExtractionService::class.java)
+
+    fun extractScheduleTime(request: ScheduleTimeExtractionRequest): ScheduleTimeExtractionResponse {
+        val prompt = generatePrompt(request)
+        val chatResponse = chatClient.prompt(prompt)
+            .call()
+            .chatResponse()
+        if (chatResponse == null) {
+            return ScheduleTimeExtractionResponse(result = false)
+        }
+        val chatAnswer = chatResponse.result.output.text
+        val response = parseChatAnswer(chatAnswer)
+        log.info("ScheduleTimeExtraction Request:\n $request \nResponse:\n $response")
+        return response
+    }
+
+    private fun parseChatAnswer(chatAnswer: String): ScheduleTimeExtractionResponse {
+        val json = chatAnswer.lines()
+            .filter { !it.contains("```") }
+            .joinToString("\n")
+        return try {
+            objectMapper.readValue(json, ScheduleTimeExtractionResponse::class.java)
+        } catch (e: JsonProcessingException) {
+            log.warn("Failed to parse JSON: $json", e)
+            ScheduleTimeExtractionResponse(result = false)
+        }
+    }
+
+    private fun generatePrompt(request: ScheduleTimeExtractionRequest): String {
+        val jsonRequest = objectMapper.writeValueAsString(request)
+        return """
+              Task: Extract time from the text and return a JSON response.
+ 
+                 - Identify time and convert it to ISO 8601 (YYYY-MM-DDTHH:MM:SS).
+                 - Remove the identified time from the text. The remaining text becomes `content`.
+                 - If no time is found, return:
+                   { "result": true, "hasTime": false}
+                 - If multiple time exists, return:
+                   { "result": false }
+ 
+                 Respond in JSON format only, with the following fields:
+                 - result
+                 - hasTime
+                 - dateTime
+                 - content
+ 
+                 No explanations.
+ 
+                 ===
+                 input:
+                 
+                 $jsonRequest
+        """.trimIndent()
+    }
+
+}
diff --git a/src/main/resources/application.yml b/src/main/resources/application.yml
index 5cbd33f3..a0064628 100644
--- a/src/main/resources/application.yml
+++ b/src/main/resources/application.yml
@@ -23,7 +23,7 @@ spring:
       enabled: false
   ai:
     openai:
-      api-key: "API_KEY_HERE"
+      api-key: "GEMINI_API_KEY_HERE"
       chat:
         base-url: "https://generativelanguage.googleapis.com/v1beta/openai/"
         options:
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/DutyparkIntegrationTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/DutyparkIntegrationTest.kt
index 8ffab3f4..cf42947c 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/DutyparkIntegrationTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/DutyparkIntegrationTest.kt
@@ -1,8 +1,6 @@
 package com.tistory.shanepark.dutypark
 
-import com.fasterxml.jackson.annotation.JsonInclude
 import com.fasterxml.jackson.databind.ObjectMapper
-import com.fasterxml.jackson.datatype.jsr310.JavaTimeModule
 import com.tistory.shanepark.dutypark.department.domain.entity.Department
 import com.tistory.shanepark.dutypark.department.repository.DepartmentRepository
 import com.tistory.shanepark.dutypark.duty.domain.entity.DutyType
@@ -47,9 +45,7 @@ class DutyparkIntegrationTest {
     @Autowired
     lateinit var jwtProvider: JwtProvider
 
-    val objectMapper: ObjectMapper = ObjectMapper()
-        .setSerializationInclusion(JsonInclude.Include.NON_NULL)
-        .registerModule(JavaTimeModule())
+    val objectMapper: ObjectMapper = TestUtils.jsr310ObjectMapper()
 
     @BeforeEach
     fun init() {
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/TestUtils.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/TestUtils.kt
new file mode 100644
index 00000000..e9ece17a
--- /dev/null
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/TestUtils.kt
@@ -0,0 +1,17 @@
+package com.tistory.shanepark.dutypark
+
+import com.fasterxml.jackson.annotation.JsonInclude
+import com.fasterxml.jackson.databind.ObjectMapper
+import com.fasterxml.jackson.datatype.jsr310.JavaTimeModule
+
+class TestUtils {
+
+    companion object {
+        fun jsr310ObjectMapper(): ObjectMapper {
+            return ObjectMapper()
+                .setSerializationInclusion(JsonInclude.Include.NON_NULL)
+                .registerModule(JavaTimeModule())
+        }
+    }
+
+}
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt
new file mode 100644
index 00000000..fbaec6d1
--- /dev/null
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt
@@ -0,0 +1,57 @@
+package com.tistory.shanepark.dutypark.schedule.timeextract.service
+
+import com.tistory.shanepark.dutypark.TestUtils.Companion.jsr310ObjectMapper
+import com.tistory.shanepark.dutypark.schedule.timeextract.domain.ScheduleTimeExtractionRequest
+import org.assertj.core.api.Assertions
+import org.junit.jupiter.api.Disabled
+import org.junit.jupiter.api.Test
+import org.springframework.ai.openai.OpenAiChatModel
+import org.springframework.ai.openai.OpenAiChatOptions
+import org.springframework.ai.openai.api.OpenAiApi
+import java.time.LocalDate
+
+
+class ScheduleTimeExtractionServiceTest {
+
+    @Test
+    @Disabled("External API test")
+    fun extractScheduleTime() {
+        val apiKey = "PUT_KEY_HERE_for_external_integration_test"
+        val openapi = OpenAiApi
+            .builder()
+            .apiKey(apiKey)
+            .baseUrl("https://generativelanguage.googleapis.com/v1beta/openai/")
+            .completionsPath("/chat/completions")
+            .build()
+
+        val chatOption = OpenAiChatOptions
+            .builder()
+            .model("gemini-2.0-flash-lite")
+            .temperature(0.0)
+            .build()
+
+        val chatModel = OpenAiChatModel
+            .builder()
+            .openAiApi(openapi)
+            .defaultOptions(chatOption)
+            .build()
+
+        val service = ScheduleTimeExtractionService(
+            chatModel = chatModel,
+            objectMapper = jsr310ObjectMapper()
+        )
+
+        val request = ScheduleTimeExtractionRequest(
+            date = LocalDate.of(2025, 2, 28),
+            content = "친구들과 밤 11시에 만나기"
+        )
+        val response = service.extractScheduleTime(request)
+
+        Assertions.assertThat(response.result).isTrue()
+        Assertions.assertThat(response.hasTime).isTrue()
+        Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T23:00:00")
+        Assertions.assertThat(response.content).doesNotContain("11시")
+    }
+
+
+}

From 113d7f92f37dcaf98859c97900aa160eeaa83f1c Mon Sep 17 00:00:00 2001
From: shane <psh40963@naver.com>
Date: Sun, 2 Mar 2025 21:09:10 +0900
Subject: [PATCH 3/7] test: ScheduleTimeExtractionService

---
 .../ScheduleTimeExtractionServiceTest.kt      | 46 +++++++++++++++++--
 1 file changed, 41 insertions(+), 5 deletions(-)

diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt
index fbaec6d1..87daa2f4 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt
@@ -16,6 +16,7 @@ class ScheduleTimeExtractionServiceTest {
     @Test
     @Disabled("External API test")
     fun extractScheduleTime() {
+        // Given
         val apiKey = "PUT_KEY_HERE_for_external_integration_test"
         val openapi = OpenAiApi
             .builder()
@@ -41,17 +42,52 @@ class ScheduleTimeExtractionServiceTest {
             objectMapper = jsr310ObjectMapper()
         )
 
-        val request = ScheduleTimeExtractionRequest(
-            date = LocalDate.of(2025, 2, 28),
-            content = "친구들과 밤 11시에 만나기"
+
+        // Then
+        val response = service.extractScheduleTime(
+            ScheduleTimeExtractionRequest(
+                date = LocalDate.of(2025, 2, 28),
+                content = "친구들과 밤 11시에 만나기"
+            )
         )
-        val response = service.extractScheduleTime(request)
 
         Assertions.assertThat(response.result).isTrue()
         Assertions.assertThat(response.hasTime).isTrue()
         Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T23:00:00")
         Assertions.assertThat(response.content).doesNotContain("11시")
-    }
 
+        val response2 = service.extractScheduleTime(
+            ScheduleTimeExtractionRequest(
+                date = LocalDate.of(2025, 2, 28),
+                content = "다섯시 저녁약속"
+            )
+        )
+        Assertions.assertThat(response2.result).isTrue()
+        Assertions.assertThat(response2.hasTime).isTrue()
+        Assertions.assertThat(response2.dateTime).isEqualTo("2025-02-28T17:00:00")
+        Assertions.assertThat(response2.content).doesNotContain("다섯시")
+
+        val response3 = service.extractScheduleTime(
+            ScheduleTimeExtractionRequest(
+                date = LocalDate.of(2025, 2, 28),
+                content = "11:30세탁기설치"
+            )
+        )
+        Assertions.assertThat(response3.result).isTrue()
+        Assertions.assertThat(response3.hasTime).isTrue()
+        Assertions.assertThat(response3.dateTime).isEqualTo("2025-02-28T11:30:00")
+        Assertions.assertThat(response3.content).doesNotContain("11:30")
+
+        val response4 = service.extractScheduleTime(
+            ScheduleTimeExtractionRequest(
+                date = LocalDate.of(2025, 2, 28),
+                content = "오사카 여행"
+            )
+        )
+        Assertions.assertThat(response4.result).isTrue()
+        Assertions.assertThat(response4.hasTime).isFalse()
+        Assertions.assertThat(response4.dateTime).isNull()
+        Assertions.assertThat(response4.content).isEqualTo("오사카 여행")
+    }
 
 }

From 26f05e363bbfad0e30ba0f7e22a3bdc799fc244b Mon Sep 17 00:00:00 2001
From: shane <psh40963@naver.com>
Date: Sun, 2 Mar 2025 21:20:41 +0900
Subject: [PATCH 4/7] chores: time extraction -> time parsing

---
 .../domain/ScheduleTimeExtractionRequest.kt   |  9 -------
 .../domain/ScheduleTimeParsingRequest.kt      |  8 ++++++
 .../domain/ScheduleTimeParsingResponse.kt}    |  7 +++--
 .../service/ScheduleTimeParsingService.kt}    | 24 ++++++++---------
 .../ScheduleTimeParsingServiceTest.kt}        | 26 +++++++++----------
 5 files changed, 36 insertions(+), 38 deletions(-)
 delete mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingRequest.kt
 rename src/main/kotlin/com/tistory/shanepark/dutypark/schedule/{timeextract/domain/ScheduleTimeExtractionResponse.kt => timeparsing/domain/ScheduleTimeParsingResponse.kt} (54%)
 rename src/main/kotlin/com/tistory/shanepark/dutypark/schedule/{timeextract/service/ScheduleTimeExtractionService.kt => timeparsing/service/ScheduleTimeParsingService.kt} (69%)
 rename src/test/kotlin/com/tistory/shanepark/dutypark/schedule/{timeextract/service/ScheduleTimeExtractionServiceTest.kt => timeparsing/service/ScheduleTimeParsingServiceTest.kt} (80%)

diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt
deleted file mode 100644
index 342641ad..00000000
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionRequest.kt
+++ /dev/null
@@ -1,9 +0,0 @@
-package com.tistory.shanepark.dutypark.schedule.timeextract.domain
-
-import java.time.LocalDate
-
-data class ScheduleTimeExtractionRequest(
-    val date: LocalDate,
-    val content: String,
-) {
-}
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingRequest.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingRequest.kt
new file mode 100644
index 00000000..efd14ec6
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingRequest.kt
@@ -0,0 +1,8 @@
+package com.tistory.shanepark.dutypark.schedule.timeparsing.domain
+
+import java.time.LocalDate
+
+data class ScheduleTimeParsingRequest(
+    val date: LocalDate,
+    val content: String,
+)
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionResponse.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingResponse.kt
similarity index 54%
rename from src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionResponse.kt
rename to src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingResponse.kt
index 37d3885c..1ba07f15 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/domain/ScheduleTimeExtractionResponse.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingResponse.kt
@@ -1,9 +1,8 @@
-package com.tistory.shanepark.dutypark.schedule.timeextract.domain
+package com.tistory.shanepark.dutypark.schedule.timeparsing.domain
 
-data class ScheduleTimeExtractionResponse(
+data class ScheduleTimeParsingResponse(
     val result: Boolean = false,
     val hasTime: Boolean = false,
     val dateTime: String? = null,
     val content: String? = null,
-) {
-}
+)
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionService.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
similarity index 69%
rename from src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionService.kt
rename to src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
index 739e3ea0..bd782fa7 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionService.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
@@ -1,46 +1,46 @@
-package com.tistory.shanepark.dutypark.schedule.timeextract.service
+package com.tistory.shanepark.dutypark.schedule.timeparsing.service
 
 import com.fasterxml.jackson.core.JsonProcessingException
 import com.fasterxml.jackson.databind.ObjectMapper
-import com.tistory.shanepark.dutypark.schedule.timeextract.domain.ScheduleTimeExtractionRequest
-import com.tistory.shanepark.dutypark.schedule.timeextract.domain.ScheduleTimeExtractionResponse
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingRequest
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingResponse
 import org.springframework.ai.chat.client.ChatClient
 import org.springframework.ai.chat.model.ChatModel
 
-class ScheduleTimeExtractionService(
+class ScheduleTimeParsingService(
     chatModel: ChatModel,
     private val objectMapper: ObjectMapper
 ) {
     private val chatClient = ChatClient.builder(chatModel).build()
-    private val log: org.slf4j.Logger = org.slf4j.LoggerFactory.getLogger(ScheduleTimeExtractionService::class.java)
+    private val log: org.slf4j.Logger = org.slf4j.LoggerFactory.getLogger(ScheduleTimeParsingService::class.java)
 
-    fun extractScheduleTime(request: ScheduleTimeExtractionRequest): ScheduleTimeExtractionResponse {
+    fun parseScheduleTime(request: ScheduleTimeParsingRequest): ScheduleTimeParsingResponse {
         val prompt = generatePrompt(request)
         val chatResponse = chatClient.prompt(prompt)
             .call()
             .chatResponse()
         if (chatResponse == null) {
-            return ScheduleTimeExtractionResponse(result = false)
+            return ScheduleTimeParsingResponse(result = false)
         }
         val chatAnswer = chatResponse.result.output.text
         val response = parseChatAnswer(chatAnswer)
-        log.info("ScheduleTimeExtraction Request:\n $request \nResponse:\n $response")
+        log.info("ScheduleTimeParsing Request:\n $request \nResponse:\n $response")
         return response
     }
 
-    private fun parseChatAnswer(chatAnswer: String): ScheduleTimeExtractionResponse {
+    private fun parseChatAnswer(chatAnswer: String): ScheduleTimeParsingResponse {
         val json = chatAnswer.lines()
             .filter { !it.contains("```") }
             .joinToString("\n")
         return try {
-            objectMapper.readValue(json, ScheduleTimeExtractionResponse::class.java)
+            objectMapper.readValue(json, ScheduleTimeParsingResponse::class.java)
         } catch (e: JsonProcessingException) {
             log.warn("Failed to parse JSON: $json", e)
-            ScheduleTimeExtractionResponse(result = false)
+            ScheduleTimeParsingResponse(result = false)
         }
     }
 
-    private fun generatePrompt(request: ScheduleTimeExtractionRequest): String {
+    private fun generatePrompt(request: ScheduleTimeParsingRequest): String {
         val jsonRequest = objectMapper.writeValueAsString(request)
         return """
               Task: Extract time from the text and return a JSON response.
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
similarity index 80%
rename from src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt
rename to src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
index 87daa2f4..3ee09db2 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeextract/service/ScheduleTimeExtractionServiceTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
@@ -1,7 +1,7 @@
-package com.tistory.shanepark.dutypark.schedule.timeextract.service
+package com.tistory.shanepark.dutypark.schedule.timeparsing.service
 
 import com.tistory.shanepark.dutypark.TestUtils.Companion.jsr310ObjectMapper
-import com.tistory.shanepark.dutypark.schedule.timeextract.domain.ScheduleTimeExtractionRequest
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingRequest
 import org.assertj.core.api.Assertions
 import org.junit.jupiter.api.Disabled
 import org.junit.jupiter.api.Test
@@ -11,11 +11,11 @@ import org.springframework.ai.openai.api.OpenAiApi
 import java.time.LocalDate
 
 
-class ScheduleTimeExtractionServiceTest {
+class ScheduleTimeParsingServiceTest {
 
     @Test
     @Disabled("External API test")
-    fun extractScheduleTime() {
+    fun parseScheduleTime() {
         // Given
         val apiKey = "PUT_KEY_HERE_for_external_integration_test"
         val openapi = OpenAiApi
@@ -37,15 +37,15 @@ class ScheduleTimeExtractionServiceTest {
             .defaultOptions(chatOption)
             .build()
 
-        val service = ScheduleTimeExtractionService(
+        val service = ScheduleTimeParsingService(
             chatModel = chatModel,
             objectMapper = jsr310ObjectMapper()
         )
 
 
         // Then
-        val response = service.extractScheduleTime(
-            ScheduleTimeExtractionRequest(
+        val response = service.parseScheduleTime(
+            ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
                 content = "친구들과 밤 11시에 만나기"
             )
@@ -56,8 +56,8 @@ class ScheduleTimeExtractionServiceTest {
         Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T23:00:00")
         Assertions.assertThat(response.content).doesNotContain("11시")
 
-        val response2 = service.extractScheduleTime(
-            ScheduleTimeExtractionRequest(
+        val response2 = service.parseScheduleTime(
+            ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
                 content = "다섯시 저녁약속"
             )
@@ -67,8 +67,8 @@ class ScheduleTimeExtractionServiceTest {
         Assertions.assertThat(response2.dateTime).isEqualTo("2025-02-28T17:00:00")
         Assertions.assertThat(response2.content).doesNotContain("다섯시")
 
-        val response3 = service.extractScheduleTime(
-            ScheduleTimeExtractionRequest(
+        val response3 = service.parseScheduleTime(
+            ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
                 content = "11:30세탁기설치"
             )
@@ -78,8 +78,8 @@ class ScheduleTimeExtractionServiceTest {
         Assertions.assertThat(response3.dateTime).isEqualTo("2025-02-28T11:30:00")
         Assertions.assertThat(response3.content).doesNotContain("11:30")
 
-        val response4 = service.extractScheduleTime(
-            ScheduleTimeExtractionRequest(
+        val response4 = service.parseScheduleTime(
+            ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
                 content = "오사카 여행"
             )

From 6ea1aef3ef0582ec9a606cf677b6306002261ebd Mon Sep 17 00:00:00 2001
From: shane <psh40963@naver.com>
Date: Mon, 3 Mar 2025 00:00:24 +0900
Subject: [PATCH 5/7] feat: LLM time parsing worker

---
 .../common/domain/entity/BaseTimeEntity.kt    |   4 +-
 .../common/domain/entity/EntityBase.kt        |  13 ++
 .../department/domain/dto/DepartmentDto.kt    |   2 +-
 .../schedule/domain/entity/Schedule.kt        |  16 ++-
 .../domain/enums/ParsingTimeStatus.kt         |   9 ++
 .../schedule/repository/ScheduleRepository.kt |   3 +
 .../schedule/service/ScheduleService.kt       |  15 ++-
 .../domain/ScheduleTimeParsingTask.kt         |  19 +++
 .../ScheduleTimeParsingQueueManager.kt        | 104 +++++++++++++++
 .../service/ScheduleTimeParsingService.kt     |   8 +-
 .../service/ScheduleTimeParsingWorker.kt      |  99 +++++++++++++++
 .../dutypark/todo/domain/entity/Todo.kt       |  10 --
 .../v2/V2.0.22__base_time_entities.sql        |  17 +++
 .../v2/V2.0.23__parsing_time_status.sql       |   2 +
 ...V2.0.24__schedule_content_without_time.sql |   2 +
 .../common/domain/BaseTimeEntityTest.kt       |   6 +-
 .../service/ScheduleTimeParsingServiceTest.kt | 118 +++++++++++-------
 17 files changed, 378 insertions(+), 69 deletions(-)
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
 create mode 100644 src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
 create mode 100644 src/main/resources/db/migration/v2/V2.0.22__base_time_entities.sql
 create mode 100644 src/main/resources/db/migration/v2/V2.0.23__parsing_time_status.sql
 create mode 100644 src/main/resources/db/migration/v2/V2.0.24__schedule_content_without_time.sql

diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/BaseTimeEntity.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/BaseTimeEntity.kt
index 68f55cdf..61069736 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/BaseTimeEntity.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/BaseTimeEntity.kt
@@ -14,10 +14,10 @@ abstract class BaseTimeEntity {
 
     @LastModifiedDate
     @Column(name = "modified_date", updatable = true)
-    var modifiedDate: LocalDateTime? = null
+    var lastModifiedDate: LocalDateTime = LocalDateTime.now()
 
     @CreatedDate
     @Column(name = "created_date", updatable = false)
-    var createdDate: LocalDateTime? = null
+    var createdDate: LocalDateTime = LocalDateTime.now()
 
 }
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/EntityBase.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/EntityBase.kt
index 626a2fa7..2e755d31 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/EntityBase.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/common/domain/entity/EntityBase.kt
@@ -5,11 +5,16 @@ import jakarta.persistence.*
 import org.hibernate.annotations.JdbcTypeCode
 import org.hibernate.proxy.HibernateProxy
 import org.hibernate.type.SqlTypes
+import org.springframework.data.annotation.CreatedDate
+import org.springframework.data.annotation.LastModifiedDate
 import org.springframework.data.domain.Persistable
+import org.springframework.data.jpa.domain.support.AuditingEntityListener
+import java.time.LocalDateTime
 import java.util.*
 import kotlin.jvm.Transient
 
 @MappedSuperclass
+@EntityListeners(AuditingEntityListener::class)
 class EntityBase : Persistable<UUID> {
 
     @Id
@@ -56,4 +61,12 @@ class EntityBase : Persistable<UUID> {
         _isNew = false
     }
 
+    @LastModifiedDate
+    @Column(name = "modified_date", updatable = true)
+    var lastModifiedDate: LocalDateTime = LocalDateTime.now()
+
+    @CreatedDate
+    @Column(name = "created_date", updatable = false)
+    var createdDate: LocalDateTime = LocalDateTime.now()
+
 }
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/department/domain/dto/DepartmentDto.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/department/domain/dto/DepartmentDto.kt
index 25fae385..3eb05a30 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/department/domain/dto/DepartmentDto.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/department/domain/dto/DepartmentDto.kt
@@ -60,7 +60,7 @@ data class DepartmentDto(
                 dutyTypes = sortedTypes,
                 members = members.map { MemberDto.ofSimple(it) },
                 createdDate = department.createdDate.toString(),
-                lastModifiedDate = department.modifiedDate.toString(),
+                lastModifiedDate = department.lastModifiedDate.toString(),
                 manager = department.manager?.name,
                 dutyBatchTemplate = department.dutyBatchTemplate?.let { DutyBatchTemplateDto(it) }
             )
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
index cbfd8ef9..2e8c4ebb 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
@@ -3,6 +3,7 @@ package com.tistory.shanepark.dutypark.schedule.domain.entity
 import com.tistory.shanepark.dutypark.common.domain.entity.EntityBase
 import com.tistory.shanepark.dutypark.member.domain.entity.Member
 import com.tistory.shanepark.dutypark.member.domain.enums.Visibility
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus
 import jakarta.persistence.*
 import java.time.LocalDateTime
 
@@ -29,9 +30,16 @@ class Schedule(
 
     @Column(name = "visibility", nullable = false)
     @Enumerated(EnumType.STRING)
-    var visibility: Visibility = Visibility.FRIENDS
+    var visibility: Visibility = Visibility.FRIENDS,
 
-) : EntityBase() {
+    @Column(name = "parsing_time_status")
+    @Enumerated(EnumType.STRING)
+    var parsingTimeStatus: ParsingTimeStatus = ParsingTimeStatus.WAIT,
+
+    ) : EntityBase() {
+
+    @Column(name = "content_without_time")
+    var contentWithoutTime: String = ""
 
     @OneToMany(mappedBy = "schedule", fetch = FetchType.LAZY, cascade = [CascadeType.ALL], orphanRemoval = true)
     val tags: MutableList<ScheduleTag> = mutableListOf()
@@ -52,4 +60,8 @@ class Schedule(
         tags.remove(scheduleTag)
     }
 
+    fun hasTimeInfo(): Boolean {
+        return startDateTime.hour != 0 || startDateTime.minute != 0
+    }
+
 }
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt
new file mode 100644
index 00000000..34e17f31
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt
@@ -0,0 +1,9 @@
+package com.tistory.shanepark.dutypark.schedule.domain.enums
+
+enum class ParsingTimeStatus {
+    WAIT,
+    PARSED,
+    NO_TIME_INFO,
+    ALREADY_HAVE_TIME_INFO,
+    FAILED,
+}
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/repository/ScheduleRepository.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/repository/ScheduleRepository.kt
index 5cf2528c..eefb290d 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/repository/ScheduleRepository.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/repository/ScheduleRepository.kt
@@ -3,6 +3,7 @@ package com.tistory.shanepark.dutypark.schedule.repository
 import com.tistory.shanepark.dutypark.member.domain.entity.Member
 import com.tistory.shanepark.dutypark.member.domain.enums.Visibility
 import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus
 import org.springframework.data.domain.Page
 import org.springframework.data.domain.Pageable
 import org.springframework.data.jpa.repository.JpaRepository
@@ -97,5 +98,7 @@ interface ScheduleRepository : JpaRepository<Schedule, UUID> {
         @Param("endOfDay") endOfDay: LocalDateTime = LocalDateTime.now().toLocalDate().atTime(23, 59, 59)
     ): List<Schedule>
 
+    fun findAllByParsingTimeStatus(parsingTimeStatus: ParsingTimeStatus): List<Schedule>
+
 }
 
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/service/ScheduleService.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/service/ScheduleService.kt
index 1715f777..b2b8454e 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/service/ScheduleService.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/service/ScheduleService.kt
@@ -8,7 +8,9 @@ import com.tistory.shanepark.dutypark.member.service.FriendService
 import com.tistory.shanepark.dutypark.schedule.domain.dto.ScheduleDto
 import com.tistory.shanepark.dutypark.schedule.domain.dto.ScheduleUpdateDto
 import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus
 import com.tistory.shanepark.dutypark.schedule.repository.ScheduleRepository
+import com.tistory.shanepark.dutypark.schedule.timeparsing.service.ScheduleTimeParsingQueueManager
 import com.tistory.shanepark.dutypark.security.domain.dto.LoginMember
 import org.springframework.stereotype.Service
 import org.springframework.transaction.annotation.Transactional
@@ -21,7 +23,8 @@ import java.util.*
 class ScheduleService(
     private val scheduleRepository: ScheduleRepository,
     private val memberRepository: MemberRepository,
-    private val friendService: FriendService
+    private val friendService: FriendService,
+    private val scheduleTimeParsingQueueManager: ScheduleTimeParsingQueueManager,
 ) {
     private val log = org.slf4j.LoggerFactory.getLogger(this.javaClass)
 
@@ -74,7 +77,6 @@ class ScheduleService(
         return array
     }
 
-
     fun createSchedule(loginMember: LoginMember, scheduleUpdateDto: ScheduleUpdateDto): Schedule {
         val scheduleMember = memberRepository.findById(scheduleUpdateDto.memberId).orElseThrow()
         checkScheduleCreateAuthority(loginMember, scheduleMember)
@@ -92,7 +94,9 @@ class ScheduleService(
         )
 
         log.info("create schedule: $scheduleUpdateDto")
-        return scheduleRepository.save(schedule)
+        scheduleRepository.save(schedule)
+        scheduleTimeParsingQueueManager.addTask(schedule)
+        return schedule
     }
 
     private fun findNextPosition(
@@ -109,9 +113,12 @@ class ScheduleService(
         schedule.content = scheduleUpdateDto.content
         schedule.description = scheduleUpdateDto.description
         schedule.visibility = scheduleUpdateDto.visibility
+        schedule.parsingTimeStatus = ParsingTimeStatus.WAIT
 
         log.info("update schedule: $scheduleUpdateDto")
-        return scheduleRepository.save(schedule)
+        scheduleRepository.save(schedule)
+        scheduleTimeParsingQueueManager.addTask(schedule)
+        return schedule
     }
 
     fun swapSchedulePosition(loginMember: LoginMember, schedule1Id: UUID, schedule2Id: UUID) {
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt
new file mode 100644
index 00000000..b534d40f
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt
@@ -0,0 +1,19 @@
+package com.tistory.shanepark.dutypark.schedule.timeparsing.domain
+
+import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
+import java.time.LocalDateTime
+import java.util.*
+
+data class ScheduleTimeParsingTask(
+    val scheduleId: UUID,
+) {
+    private val requestDateTime: LocalDateTime = LocalDateTime.now()
+
+    fun isExpired(schedule: Schedule): Boolean {
+        if (schedule.id != scheduleId) {
+            throw IllegalArgumentException("Schedule ID does not match: ${schedule.id} != $scheduleId")
+        }
+        return schedule.lastModifiedDate.isAfter(requestDateTime)
+    }
+}
+
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
new file mode 100644
index 00000000..152a8d71
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
@@ -0,0 +1,104 @@
+package com.tistory.shanepark.dutypark.schedule.timeparsing.service
+
+import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus
+import com.tistory.shanepark.dutypark.schedule.repository.ScheduleRepository
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingTask
+import jakarta.annotation.PostConstruct
+import org.slf4j.LoggerFactory
+import org.springframework.stereotype.Component
+import java.time.LocalDateTime
+import java.util.*
+import java.util.concurrent.ConcurrentLinkedQueue
+import java.util.concurrent.Executors
+import java.util.concurrent.TimeUnit
+import java.util.concurrent.atomic.AtomicBoolean
+
+@Component
+class ScheduleTimeParsingQueueManager(
+    private val worker: ScheduleTimeParsingWorker,
+    private val scheduleRepository: ScheduleRepository,
+) {
+    private val log = LoggerFactory.getLogger(ScheduleTimeParsingQueueManager::class.java)
+    private val executorService = Executors.newSingleThreadExecutor()
+    private val queue = ConcurrentLinkedQueue<ScheduleTimeParsingTask>()
+    private val isRunning = AtomicBoolean(false)
+
+    private val completedTasks: Queue<LocalDateTime> = ConcurrentLinkedQueue()
+    private val completedDailyTasks: Queue<LocalDateTime> = ConcurrentLinkedQueue()
+
+    private val rpmLimit = 30
+    private val rpdLimit = 1500
+
+    @PostConstruct
+    fun init() {
+        val allWaitJobs = scheduleRepository.findAllByParsingTimeStatus(ParsingTimeStatus.WAIT)
+        allWaitJobs.forEach { schedule -> addTask(schedule) }
+        log.info("${allWaitJobs.size} schedules are added to the queue.")
+    }
+
+    fun addTask(schedule: Schedule) {
+        queue.add(ScheduleTimeParsingTask(schedule.id))
+        startWorkIfNeeded()
+    }
+
+    private fun startWorkIfNeeded() {
+        if (queue.isEmpty() || !isRunning.compareAndSet(false, true)) return
+
+        executorService.execute {
+            try {
+                // wait enough til schedule transaction is committed
+                TimeUnit.SECONDS.sleep(10)
+                run()
+            } finally {
+                isRunning.set(false)
+            }
+        }
+    }
+
+    private fun run() {
+        while (queue.isNotEmpty()) {
+            while (shouldWait()) {
+                log.info("Waiting for API rate limit...")
+                TimeUnit.MINUTES.sleep(1)
+            }
+
+            val task = queue.poll() ?: continue
+            worker.run(task)
+            recordCompletion()
+        }
+    }
+
+    private fun shouldWait(): Boolean {
+        val now = LocalDateTime.now()
+
+        completedTasks.peek()?.let {
+            if (completedTasks.size >= rpmLimit && it.isAfter(now.minusMinutes(1))) {
+                return true
+            }
+        }
+
+        completedDailyTasks.peek()?.let {
+            if (completedDailyTasks.size >= rpdLimit && it.isAfter(now.minusDays(1))) {
+                return true
+            }
+        }
+
+        return false
+    }
+
+    private fun recordCompletion() {
+        val now = LocalDateTime.now()
+
+        completedTasks.add(now)
+        while (completedTasks.size > rpmLimit) {
+            completedTasks.poll()
+        }
+
+        completedDailyTasks.add(now)
+        while (completedDailyTasks.size > rpdLimit) {
+            completedDailyTasks.poll()
+        }
+    }
+
+}
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
index bd782fa7..e7c542c5 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
@@ -6,10 +6,12 @@ import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimePa
 import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingResponse
 import org.springframework.ai.chat.client.ChatClient
 import org.springframework.ai.chat.model.ChatModel
+import org.springframework.stereotype.Service
 
+@Service
 class ScheduleTimeParsingService(
     chatModel: ChatModel,
-    private val objectMapper: ObjectMapper
+    private val objectMapper: ObjectMapper,
 ) {
     private val chatClient = ChatClient.builder(chatModel).build()
     private val log: org.slf4j.Logger = org.slf4j.LoggerFactory.getLogger(ScheduleTimeParsingService::class.java)
@@ -24,7 +26,7 @@ class ScheduleTimeParsingService(
         }
         val chatAnswer = chatResponse.result.output.text
         val response = parseChatAnswer(chatAnswer)
-        log.info("ScheduleTimeParsing Request:\n $request \nResponse:\n $response")
+        log.info("ScheduleTimeParsing==\n $request \nResponse:\n $response\n")
         return response
     }
 
@@ -35,7 +37,7 @@ class ScheduleTimeParsingService(
         return try {
             objectMapper.readValue(json, ScheduleTimeParsingResponse::class.java)
         } catch (e: JsonProcessingException) {
-            log.warn("Failed to parse JSON: $json", e)
+            log.warn("Failed to parse JSON:\n$json", e)
             ScheduleTimeParsingResponse(result = false)
         }
     }
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
new file mode 100644
index 00000000..2b4d43f4
--- /dev/null
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
@@ -0,0 +1,99 @@
+package com.tistory.shanepark.dutypark.schedule.timeparsing.service
+
+import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus.*
+import com.tistory.shanepark.dutypark.schedule.repository.ScheduleRepository
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingRequest
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingResponse
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingTask
+import org.slf4j.Logger
+import org.slf4j.LoggerFactory
+import org.springframework.stereotype.Service
+import java.time.LocalDate
+import java.time.LocalDateTime
+import java.time.format.DateTimeParseException
+
+/**
+ * Do not use @Transaction dirty checking since it will be on another thread.
+ */
+@Service
+class ScheduleTimeParsingWorker(
+    private val scheduleTimeParsingService: ScheduleTimeParsingService,
+    private val scheduleRepository: ScheduleRepository,
+) {
+    private val log: Logger = LoggerFactory.getLogger(ScheduleTimeParsingWorker::class.java)
+
+    fun run(task: ScheduleTimeParsingTask) {
+        val scheduleOption = scheduleRepository.findById(task.scheduleId)
+        if (scheduleOption.isEmpty) {
+            log.info("Schedule not found. maybe already deleted. scheduleId: ${task.scheduleId}")
+            return
+        }
+        val schedule = scheduleOption.get()
+        if (task.isExpired(schedule)) {
+            log.info("Schedule is updated, skip parsing. scheduleId: ${task.scheduleId}")
+            return
+        }
+
+        if (alreadyHaveTimeInfo(schedule)) return
+
+        val request = ScheduleTimeParsingRequest(
+            date = LocalDate.of(
+                schedule.startDateTime.year,
+                schedule.startDateTime.monthValue,
+                schedule.startDateTime.dayOfMonth,
+            ),
+            content = schedule.content
+        )
+        val response = scheduleTimeParsingService.parseScheduleTime(request)
+
+        if (responseFail(response, schedule)) return
+        if (haveNoTimeInfo(response, schedule)) return
+
+        try {
+            val parsed: LocalDateTime = LocalDateTime.parse(response.dateTime.toString())
+            schedule.parsingTimeStatus = PARSED
+            schedule.startDateTime = parsed
+            schedule.contentWithoutTime = response.content ?: ""
+            scheduleRepository.save(schedule)
+        } catch (e: DateTimeParseException) {
+            log.warn("Failed to parse dateTime: $response")
+            schedule.parsingTimeStatus = FAILED
+            scheduleRepository.save(schedule)
+        }
+    }
+
+    private fun haveNoTimeInfo(
+        response: ScheduleTimeParsingResponse,
+        schedule: Schedule
+    ): Boolean {
+        if (response.hasTime) {
+            return false
+        }
+        schedule.parsingTimeStatus = NO_TIME_INFO
+        scheduleRepository.save(schedule)
+        return true
+    }
+
+    private fun responseFail(
+        response: ScheduleTimeParsingResponse,
+        schedule: Schedule
+    ): Boolean {
+        if (response.result) {
+            return false
+        }
+        schedule.parsingTimeStatus = FAILED
+        scheduleRepository.save(schedule)
+        return true
+    }
+
+    private fun alreadyHaveTimeInfo(schedule: Schedule): Boolean {
+        if (schedule.hasTimeInfo()) {
+            schedule.parsingTimeStatus = ALREADY_HAVE_TIME_INFO
+            scheduleRepository.save(schedule)
+            return true
+        }
+        return false
+    }
+
+}
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/todo/domain/entity/Todo.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/todo/domain/entity/Todo.kt
index 6bf9f40d..32d541ff 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/todo/domain/entity/Todo.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/todo/domain/entity/Todo.kt
@@ -3,11 +3,8 @@ package com.tistory.shanepark.dutypark.todo.domain.entity
 import com.tistory.shanepark.dutypark.common.domain.entity.EntityBase
 import com.tistory.shanepark.dutypark.member.domain.entity.Member
 import jakarta.persistence.*
-import org.springframework.data.jpa.domain.support.AuditingEntityListener
-import java.time.LocalDateTime
 
 @Entity
-@EntityListeners(AuditingEntityListener::class)
 class Todo(
     @ManyToOne(fetch = FetchType.LAZY)
     @JoinColumn(name = "member_id", nullable = false)
@@ -27,13 +24,6 @@ class Todo(
     fun update(title: String, content: String) {
         this.title = title
         this.content = content
-        this.modifiedDate = LocalDateTime.now()
     }
 
-    @Column(name = "modified_date", updatable = true)
-    var modifiedDate: LocalDateTime = LocalDateTime.now()
-
-    @Column(name = "created_date", updatable = false)
-    val createdDate: LocalDateTime = LocalDateTime.now()
-
 }
diff --git a/src/main/resources/db/migration/v2/V2.0.22__base_time_entities.sql b/src/main/resources/db/migration/v2/V2.0.22__base_time_entities.sql
new file mode 100644
index 00000000..ec0e833a
--- /dev/null
+++ b/src/main/resources/db/migration/v2/V2.0.22__base_time_entities.sql
@@ -0,0 +1,17 @@
+alter table holiday
+    add column created_date  datetime,
+    add column modified_date datetime;
+
+update holiday
+set created_date  = now(),
+    modified_date = now()
+where created_date is null;
+
+alter table schedule
+    add column created_date  datetime,
+    add column modified_date datetime;
+
+update schedule
+set created_date  = now(),
+    modified_date = now()
+where created_date is null;
diff --git a/src/main/resources/db/migration/v2/V2.0.23__parsing_time_status.sql b/src/main/resources/db/migration/v2/V2.0.23__parsing_time_status.sql
new file mode 100644
index 00000000..4692ecb1
--- /dev/null
+++ b/src/main/resources/db/migration/v2/V2.0.23__parsing_time_status.sql
@@ -0,0 +1,2 @@
+alter table schedule
+    add column parsing_time_status varchar(255) default 'WAIT';
diff --git a/src/main/resources/db/migration/v2/V2.0.24__schedule_content_without_time.sql b/src/main/resources/db/migration/v2/V2.0.24__schedule_content_without_time.sql
new file mode 100644
index 00000000..7fa81dda
--- /dev/null
+++ b/src/main/resources/db/migration/v2/V2.0.24__schedule_content_without_time.sql
@@ -0,0 +1,2 @@
+alter table schedule
+    add column content_without_time varchar(50) default ''
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/common/domain/BaseTimeEntityTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/common/domain/BaseTimeEntityTest.kt
index 99f86a67..22e9d387 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/common/domain/BaseTimeEntityTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/common/domain/BaseTimeEntityTest.kt
@@ -21,8 +21,8 @@ class BaseTimeEntityTest : DutyparkIntegrationTest() {
         refreshTokenRepository.save(refreshToken)
 
         assertThat(refreshToken.createdDate).isNotNull
-        assertThat(refreshToken.modifiedDate).isNotNull
-        assertThat(refreshToken.createdDate).isSameAs(refreshToken.modifiedDate)
+        assertThat(refreshToken.lastModifiedDate).isNotNull
+        assertThat(refreshToken.createdDate).isSameAs(refreshToken.lastModifiedDate)
 
         // When
         refreshToken.validUntil = LocalDateTime.now()
@@ -30,7 +30,7 @@ class BaseTimeEntityTest : DutyparkIntegrationTest() {
 
         // Then
         val saved = refreshTokenRepository.save(refreshToken)
-        assertThat(saved.modifiedDate).isAfter(refreshToken.createdDate)
+        assertThat(saved.lastModifiedDate).isAfter(refreshToken.createdDate)
     }
 
 }
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
index 3ee09db2..6e377127 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
@@ -13,37 +13,12 @@ import java.time.LocalDate
 
 class ScheduleTimeParsingServiceTest {
 
+    private val apiKey = "PUT_KEY_HERE_for_external_integration_test"
+    val service = makeService()
+
     @Test
     @Disabled("External API test")
-    fun parseScheduleTime() {
-        // Given
-        val apiKey = "PUT_KEY_HERE_for_external_integration_test"
-        val openapi = OpenAiApi
-            .builder()
-            .apiKey(apiKey)
-            .baseUrl("https://generativelanguage.googleapis.com/v1beta/openai/")
-            .completionsPath("/chat/completions")
-            .build()
-
-        val chatOption = OpenAiChatOptions
-            .builder()
-            .model("gemini-2.0-flash-lite")
-            .temperature(0.0)
-            .build()
-
-        val chatModel = OpenAiChatModel
-            .builder()
-            .openAiApi(openapi)
-            .defaultOptions(chatOption)
-            .build()
-
-        val service = ScheduleTimeParsingService(
-            chatModel = chatModel,
-            objectMapper = jsr310ObjectMapper()
-        )
-
-
-        // Then
+    fun parseScheduleTime1() {
         val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
@@ -55,39 +30,94 @@ class ScheduleTimeParsingServiceTest {
         Assertions.assertThat(response.hasTime).isTrue()
         Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T23:00:00")
         Assertions.assertThat(response.content).doesNotContain("11시")
+    }
 
-        val response2 = service.parseScheduleTime(
+    @Test
+    @Disabled("External API test")
+    fun parseScheduleTime2() {
+        val service = makeService()
+        val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
                 content = "다섯시 저녁약속"
             )
         )
-        Assertions.assertThat(response2.result).isTrue()
-        Assertions.assertThat(response2.hasTime).isTrue()
-        Assertions.assertThat(response2.dateTime).isEqualTo("2025-02-28T17:00:00")
-        Assertions.assertThat(response2.content).doesNotContain("다섯시")
+        Assertions.assertThat(response.result).isTrue()
+        Assertions.assertThat(response.hasTime).isTrue()
+        Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T17:00:00")
+        Assertions.assertThat(response.content).doesNotContain("다섯시")
+    }
 
-        val response3 = service.parseScheduleTime(
+    @Test
+    @Disabled("External API test")
+    fun parseScheduleTime3() {
+        val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
                 content = "11:30세탁기설치"
             )
         )
-        Assertions.assertThat(response3.result).isTrue()
-        Assertions.assertThat(response3.hasTime).isTrue()
-        Assertions.assertThat(response3.dateTime).isEqualTo("2025-02-28T11:30:00")
-        Assertions.assertThat(response3.content).doesNotContain("11:30")
+        Assertions.assertThat(response.result).isTrue()
+        Assertions.assertThat(response.hasTime).isTrue()
+        Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T11:30:00")
+        Assertions.assertThat(response.content).doesNotContain("11:30")
+    }
 
-        val response4 = service.parseScheduleTime(
+    @Test
+    @Disabled("External API test")
+    fun parseScheduleTime4() {
+        val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
                 content = "오사카 여행"
             )
         )
-        Assertions.assertThat(response4.result).isTrue()
-        Assertions.assertThat(response4.hasTime).isFalse()
-        Assertions.assertThat(response4.dateTime).isNull()
-        Assertions.assertThat(response4.content).isEqualTo("오사카 여행")
+        Assertions.assertThat(response.result).isTrue()
+        Assertions.assertThat(response.hasTime).isFalse()
+        Assertions.assertThat(response.dateTime).isNull()
+        Assertions.assertThat(response.content).isEqualTo("오사카 여행")
+    }
+
+    @Test
+    @Disabled("External API test")
+    fun parseScheduleTime5() {
+        val response = service.parseScheduleTime(
+            ScheduleTimeParsingRequest(
+                date = LocalDate.of(2025, 2, 28),
+                content = "테니스 2시~4시"
+            )
+        )
+        Assertions.assertThat(response.result).isTrue()
+        Assertions.assertThat(response.hasTime).isFalse()
+        Assertions.assertThat(response.dateTime).isNull()
+        Assertions.assertThat(response.content).isEqualTo("2시")
+    }
+
+    private fun makeService(): ScheduleTimeParsingService {
+        val openapi = OpenAiApi
+            .builder()
+            .apiKey(apiKey)
+            .baseUrl("https://generativelanguage.googleapis.com/v1beta/openai/")
+            .completionsPath("/chat/completions")
+            .build()
+
+        val chatOption = OpenAiChatOptions
+            .builder()
+            .model("gemini-2.0-flash-lite")
+            .temperature(0.0)
+            .build()
+
+        val chatModel = OpenAiChatModel
+            .builder()
+            .openAiApi(openapi)
+            .defaultOptions(chatOption)
+            .build()
+
+        val service = ScheduleTimeParsingService(
+            chatModel = chatModel,
+            objectMapper = jsr310ObjectMapper()
+        )
+        return service
     }
 
 }

From f2919d3660600286c0fb6be9558c551ca75c4614 Mon Sep 17 00:00:00 2001
From: shane <psh40963@naver.com>
Date: Mon, 3 Mar 2025 11:36:06 +0900
Subject: [PATCH 6/7] feat: LLM time parsing supports time range

---
 dutypark_secret                               |   2 +-
 .../schedule/domain/dto/ScheduleDto.kt        |   4 +-
 .../schedule/domain/entity/Schedule.kt        |   4 +
 .../domain/enums/ParsingTimeStatus.kt         |   1 +
 .../domain/ScheduleTimeParsingResponse.kt     |   3 +-
 .../domain/ScheduleTimeParsingTask.kt         |   5 +-
 .../ScheduleTimeParsingQueueManager.kt        |   6 +-
 .../service/ScheduleTimeParsingService.kt     |  14 +-
 .../service/ScheduleTimeParsingWorker.kt      |  10 +-
 .../v2/V2.0.25__skip_parse_old_schedules.sql  |   3 +
 src/main/resources/static/css/base.css        |  26 +--
 src/main/resources/templates/duty/duty.html   | 156 +++++++++++-------
 .../resources/templates/layout/layout.html    |  11 +-
 .../service/ScheduleTimeParsingServiceTest.kt |  64 +++++--
 14 files changed, 202 insertions(+), 107 deletions(-)
 create mode 100644 src/main/resources/db/migration/v2/V2.0.25__skip_parse_old_schedules.sql

diff --git a/dutypark_secret b/dutypark_secret
index 5a71c824..fd28022c 160000
--- a/dutypark_secret
+++ b/dutypark_secret
@@ -1 +1 @@
-Subproject commit 5a71c824ffa2b8b3820be68e0ca7389b124cafb0
+Subproject commit fd28022cf9dcfc39856ea8e71d90eee2c6081506
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/dto/ScheduleDto.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/dto/ScheduleDto.kt
index 4110d884..320e3cba 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/dto/ScheduleDto.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/dto/ScheduleDto.kt
@@ -32,7 +32,7 @@ data class ScheduleDto(
         fun ofSimple(member: Member, schedule: Schedule): ScheduleDto {
             return ScheduleDto(
                 id = schedule.id,
-                content = schedule.content,
+                content = schedule.content(),
                 position = schedule.position,
                 year = schedule.startDateTime.year,
                 month = schedule.startDateTime.monthValue,
@@ -57,7 +57,7 @@ data class ScheduleDto(
             return validDays.map {
                 ScheduleDto(
                     id = schedule.id,
-                    content = schedule.content,
+                    content = schedule.content(),
                     description = schedule.description,
                     position = schedule.position,
                     year = it.year,
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
index 2e8c4ebb..334991b8 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
@@ -64,4 +64,8 @@ class Schedule(
         return startDateTime.hour != 0 || startDateTime.minute != 0
     }
 
+    fun content(): String {
+        return contentWithoutTime.ifBlank { content }
+    }
+
 }
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt
index 34e17f31..9d07c5cd 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/enums/ParsingTimeStatus.kt
@@ -2,6 +2,7 @@ package com.tistory.shanepark.dutypark.schedule.domain.enums
 
 enum class ParsingTimeStatus {
     WAIT,
+    SKIP,
     PARSED,
     NO_TIME_INFO,
     ALREADY_HAVE_TIME_INFO,
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingResponse.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingResponse.kt
index 1ba07f15..0a7f7569 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingResponse.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingResponse.kt
@@ -3,6 +3,7 @@ package com.tistory.shanepark.dutypark.schedule.timeparsing.domain
 data class ScheduleTimeParsingResponse(
     val result: Boolean = false,
     val hasTime: Boolean = false,
-    val dateTime: String? = null,
+    val startDateTime: String? = null,
+    val endDateTime: String? = null,
     val content: String? = null,
 )
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt
index b534d40f..b6f08f8c 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/domain/ScheduleTimeParsingTask.kt
@@ -13,7 +13,10 @@ data class ScheduleTimeParsingTask(
         if (schedule.id != scheduleId) {
             throw IllegalArgumentException("Schedule ID does not match: ${schedule.id} != $scheduleId")
         }
-        return schedule.lastModifiedDate.isAfter(requestDateTime)
+        return schedule.lastModifiedDate
+            .minusSeconds(1)
+            .isAfter(requestDateTime)
     }
+
 }
 
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
index 152a8d71..0d9b97c8 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
@@ -1,7 +1,7 @@
 package com.tistory.shanepark.dutypark.schedule.timeparsing.service
 
 import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
-import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus.WAIT
 import com.tistory.shanepark.dutypark.schedule.repository.ScheduleRepository
 import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingTask
 import jakarta.annotation.PostConstruct
@@ -32,12 +32,14 @@ class ScheduleTimeParsingQueueManager(
 
     @PostConstruct
     fun init() {
-        val allWaitJobs = scheduleRepository.findAllByParsingTimeStatus(ParsingTimeStatus.WAIT)
+        val allWaitJobs = scheduleRepository.findAllByParsingTimeStatus(WAIT)
         allWaitJobs.forEach { schedule -> addTask(schedule) }
         log.info("${allWaitJobs.size} schedules are added to the queue.")
     }
 
     fun addTask(schedule: Schedule) {
+        if (schedule.parsingTimeStatus != WAIT)
+            return
         queue.add(ScheduleTimeParsingTask(schedule.id))
         startWorkIfNeeded()
     }
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
index e7c542c5..a8df39c4 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingService.kt
@@ -48,18 +48,22 @@ class ScheduleTimeParsingService(
               Task: Extract time from the text and return a JSON response.
  
                  - Identify time and convert it to ISO 8601 (YYYY-MM-DDTHH:MM:SS).
+                 - If a time range is mentioned (e.g., "2시~4시"), assign the first time to `startDateTime` and the second time to `endDateTime`.
+                 - If only one time is mentioned, set both `startDateTime` and `endDateTime` to the same value.
                  - Remove the identified time from the text. The remaining text becomes `content`.
+                 - if AM/PM is not specified, assume based on the content.
                  - If no time is found, return:
-                   { "result": true, "hasTime": false}
-                 - If multiple time exists, return:
+                   { "result": true, "hasTime": false }
+                 - If more than two time exist, return:
                    { "result": false }
- 
+    
                  Respond in JSON format only, with the following fields:
                  - result
                  - hasTime
-                 - dateTime
+                 - startDateTime
+                 - endDateTime
                  - content
- 
+     
                  No explanations.
  
                  ===
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
index 2b4d43f4..9b8ee6d6 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
@@ -14,7 +14,7 @@ import java.time.LocalDateTime
 import java.time.format.DateTimeParseException
 
 /**
- * Do not use @Transaction dirty checking since it will be on another thread.
+ * Do not use @Transaction dirty checking since it will be working on another thread.
  */
 @Service
 class ScheduleTimeParsingWorker(
@@ -51,9 +51,11 @@ class ScheduleTimeParsingWorker(
         if (haveNoTimeInfo(response, schedule)) return
 
         try {
-            val parsed: LocalDateTime = LocalDateTime.parse(response.dateTime.toString())
+            val parsedStart = LocalDateTime.parse(response.startDateTime.toString())
+            val parsedEnd = LocalDateTime.parse(response.endDateTime.toString())
             schedule.parsingTimeStatus = PARSED
-            schedule.startDateTime = parsed
+            schedule.startDateTime = parsedStart
+            schedule.endDateTime = parsedEnd
             schedule.contentWithoutTime = response.content ?: ""
             scheduleRepository.save(schedule)
         } catch (e: DateTimeParseException) {
@@ -88,7 +90,7 @@ class ScheduleTimeParsingWorker(
     }
 
     private fun alreadyHaveTimeInfo(schedule: Schedule): Boolean {
-        if (schedule.hasTimeInfo()) {
+        if (schedule.hasTimeInfo() || schedule.startDateTime != schedule.endDateTime) {
             schedule.parsingTimeStatus = ALREADY_HAVE_TIME_INFO
             scheduleRepository.save(schedule)
             return true
diff --git a/src/main/resources/db/migration/v2/V2.0.25__skip_parse_old_schedules.sql b/src/main/resources/db/migration/v2/V2.0.25__skip_parse_old_schedules.sql
new file mode 100644
index 00000000..9575d2a8
--- /dev/null
+++ b/src/main/resources/db/migration/v2/V2.0.25__skip_parse_old_schedules.sql
@@ -0,0 +1,3 @@
+update schedule
+set parsing_time_status = 'SKIP'
+where start_date_time < '2025-01-01 00:00:00';
diff --git a/src/main/resources/static/css/base.css b/src/main/resources/static/css/base.css
index de5ccd28..86886619 100644
--- a/src/main/resources/static/css/base.css
+++ b/src/main/resources/static/css/base.css
@@ -413,18 +413,22 @@ a.homeButton:hover {
     margin: 10px;
 }
 
-#detail-view-modal .schedules .schedule.visibility-private {
-    background-color: mistyrose;
-}
-
-#detail-view-modal .schedules .schedule.visibility-public {
+#detail-view-modal .schedules .schedule.visibility-PUBLIC {
     background-color: honeydew;
 }
 
-#detail-view-modal .schedules .schedule.visibility-friends {
+#detail-view-modal .schedules .schedule.visibility-FRIENDS {
     background-color: aliceblue;
 }
 
+#detail-view-modal .schedules .schedule.visibility-FAMILY {
+    background-color: moccasin;
+}
+
+#detail-view-modal .schedules .schedule.visibility-PRIVATE {
+    background-color: mistyrose;
+}
+
 .schedules .schedule .schedule-content {
     margin: 0;
     padding: 0;
@@ -438,13 +442,15 @@ a.homeButton:hover {
     display: none;
 }
 
-.schedule-add .content-length,
+.schedule-edit {
+    display: grid;
+}
+
 .schedule-edit .content-length {
     font-size: 0.6em;
     color: #333;
 }
 
-.schedule-add textarea,
 .schedule-edit textarea {
     font-size: 1em;
 }
@@ -540,10 +546,6 @@ a.homeButton:hover {
     text-align: right;
 }
 
-.shadow {
-    box-shadow: 2px 4px 7px 3px #eaeaea;
-}
-
 .navbar {
     font-size: 1.5em;
     color: rgba(255, 255, 255, 0.55);
diff --git a/src/main/resources/templates/duty/duty.html b/src/main/resources/templates/duty/duty.html
index f90a636c..4521d838 100644
--- a/src/main/resources/templates/duty/duty.html
+++ b/src/main/resources/templates/duty/duty.html
@@ -394,14 +394,14 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
             </form>
           </div>
           <div class="schedules mt-4">
-            <div id="schedule-edit" class="schedule card shadow"
+            <div class="schedule card shadow"
                  v-if="!isCreateScheduleMode && (editingSchedule.id == null || isEditing(schedule) )"
-                 :class="{'visibility-public': schedule.visibility == 'PUBLIC', 'visibility-friends': schedule.visibility == 'FRIENDS', 'visibility-private': schedule.visibility == 'PRIVATE'}"
+                 :class="['visibility-' + schedule.visibility]"
                  v-for="(schedule, s_index) in schedulesByDays[detailView.index]"
                  :id="'schedule-' + schedule.id">
               <div v-if="!isEditing(schedule)" v-html="printSchedule(schedule)"></div>
               <div v-if="isEditing(schedule)" class="schedule-edit">
-                <label>일정 추가 <span class="content-length"
+                <label>일정 제목 <span class="content-length"
                                    v-text="editingSchedule.content.length + ' / ' + schedule_content_max_length"></span>
                   <small class="help-note">달력에 표시되는 제목이에요 <i class="bi bi-info-circle-fill"></i></small>
                 </label>
@@ -412,25 +412,36 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                 </label>
                 <textarea class="form-control" placeholder="(선택사항) 일정 상세정보를 입력하세요." rows="4"
                           v-model="editingSchedule.description"></textarea>
-                <label>시작일</label>
-                <input type="datetime-local" class="form-control"
-                       v-model="editingSchedule.startDateTime"/>
-                <label>종료일 (선택사항)</label>
-                <input type="datetime-local" class="form-control"
-                       v-model="editingSchedule.endDateTime"/>
+                <label>시작일
+                  <input type="date" class="form-control" v-model="editingSchedule.startDate" readonly/>
+                </label>
+                <label>시작시간 (선택사항)
+                  <input type="time" class="form-control" v-model="editingSchedule.startTime"/>
+                </label>
+                <label>종료일 (선택사항)
+                  <input type="datetime-local" class="form-control"
+                         v-model="editingSchedule.endDateTime"/>
+                </label>
                 <label>공개설정</label>
                 <div class="schedule-visibility">
                   <div class="pretty p-default p-curve">
                     <input type="radio" value="PUBLIC" v-model="editingSchedule.visibility"/>
                     <div class="state p-success-o">
-                      <label>전체공개</label>
+                      <label>전체</label>
                     </div>
                   </div>
 
                   <div class="pretty p-default p-curve">
                     <input type="radio" value="FRIENDS" v-model="editingSchedule.visibility"/>
                     <div class="state p-warning-o">
-                      <label>친구공개</label>
+                      <label>친구</label>
+                    </div>
+                  </div>
+
+                  <div class="pretty p-default p-curve">
+                    <input type="radio" value="FAMILY" v-model="editingSchedule.visibility"/>
+                    <div class="state p-warning-o">
+                      <label>가족</label>
                     </div>
                   </div>
 
@@ -471,57 +482,63 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                 <button class="btn btn-secondary" v-on:click="cancelEditMode()">취소</button>
               </div>
             </div>
-            <div id="schedule-create" class="schedule schedule-add card shadow" v-if="isCreateScheduleMode">
-              <label>일정 제목 <span class="content-length"
-                                 v-text="createSchedule.content.length + ' / ' + schedule_content_max_length"></span>
-                <small class="help-note">달력에 표시되는 제목이에요 <i class="bi bi-info-circle-fill"></i></small>
-                <input class="form-control" placeholder="일정 제목을 입력하세요." :maxlength="schedule_content_max_length"
-                       v-model="createSchedule.content"/>
-              </label>
-              <label>일정 상세<small class="help-note">달력에 표시되지 않고 클릭했을때만 보여져요 <i
-                  class="bi bi-info-circle-fill"></i></small>
-                <textarea class="form-control" placeholder="(선택사항) 일정 상세정보를 입력하세요." rows="4"
-                          v-model="createSchedule.description"></textarea>
-              </label>
-              <label>시작일</label>
-              <input type="datetime-local" class="form-control"
-                     v-model="createSchedule.startDateTime"/>
-              <label>종료일 (선택사항)</label>
-              <input type="datetime-local" class="form-control" v-model="createSchedule.endDateTime"
-                     :min="createSchedule.startDateTime"/>
-              <label>공개설정</label>
-              <div class="schedule-visibility">
-                <div class="pretty p-default p-curve">
-                  <input type="radio" value="PUBLIC" v-model="createSchedule.visibility"/>
-                  <div class="state p-success-o">
-                    <label>전체공개</label>
+            <div class="schedule card shadow" v-if="isCreateScheduleMode">
+              <div class="schedule-edit">
+                <label>일정 추가 <span class="content-length"
+                                   v-text="createSchedule.content.length + ' / ' + schedule_content_max_length"></span>
+                  <small class="help-note">달력에 표시되는 제목이에요 <i class="bi bi-info-circle-fill"></i></small>
+                  <input class="form-control" placeholder="일정 제목을 입력하세요." :maxlength="schedule_content_max_length"
+                         v-model="createSchedule.content"/>
+                </label>
+                <label>일정 상세<small class="help-note">달력에 표시되지 않고 클릭했을때만 보여져요 <i
+                    class="bi bi-info-circle-fill"></i></small>
+                  <textarea class="form-control" placeholder="(선택사항) 일정 상세정보를 입력하세요." rows="4"
+                            v-model="createSchedule.description"></textarea>
+                </label>
+                <label>시작일
+                  <input type="date" class="form-control" v-model="createSchedule.startDate" readonly/>
+                </label>
+                <label>시작시간 (선택사항)
+                  <input type="time" class="form-control" v-model="createSchedule.startTime"/>
+                </label>
+                <label>종료일시 (선택사항)
+                  <input type="datetime-local" class="form-control" v-model="createSchedule.endDateTime"
+                         :min="createSchedule.startDateTime"/>
+                </label>
+                <label>공개설정</label>
+                <div class="schedule-visibility">
+                  <div class="pretty p-default p-curve">
+                    <input type="radio" value="PUBLIC" v-model="createSchedule.visibility"/>
+                    <div class="state p-success-o">
+                      <label>전체</label>
+                    </div>
                   </div>
-                </div>
 
-                <div class="pretty p-default p-curve">
-                  <input type="radio" value="FRIENDS" v-model="createSchedule.visibility"/>
-                  <div class="state p-info-o">
-                    <label>친구공개</label>
+                  <div class="pretty p-default p-curve">
+                    <input type="radio" value="FRIENDS" v-model="createSchedule.visibility"/>
+                    <div class="state p-info-o">
+                      <label>친구</label>
+                    </div>
                   </div>
-                </div>
 
-                <div class="pretty p-default p-curve">
-                  <input type="radio" value="FAMILY" v-model="createSchedule.visibility"/>
-                  <div class="state p-warning-o">
-                    <label>가족공개</label>
+                  <div class="pretty p-default p-curve">
+                    <input type="radio" value="FAMILY" v-model="createSchedule.visibility"/>
+                    <div class="state p-warning-o">
+                      <label>가족</label>
+                    </div>
                   </div>
-                </div>
 
-                <div class="pretty p-default p-curve">
-                  <input type="radio" value="PRIVATE" v-model="createSchedule.visibility"/>
-                  <div class="state p-danger-o">
-                    <label>비공개</label>
+                  <div class="pretty p-default p-curve">
+                    <input type="radio" value="PRIVATE" v-model="createSchedule.visibility"/>
+                    <div class="state p-danger-o">
+                      <label>비공개</label>
+                    </div>
                   </div>
                 </div>
-              </div>
-              <div class="buttons mt-3">
-                <button id="add-btn" class="btn btn-success" v-on:click="saveSchedule">추가</button>
-                <button class="btn btn-secondary" v-on:click="cancelCreateSchedule">취소</button>
+                <div class="buttons mt-3">
+                  <button id="add-btn" class="btn btn-success" v-on:click="saveSchedule">추가</button>
+                  <button class="btn btn-secondary" v-on:click="cancelCreateSchedule">취소</button>
+                </div>
               </div>
             </div>
           </div>
@@ -563,7 +580,14 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                     department: {},
                     dDays: [],
                     selectedDday: null,
-                    detailView: null,
+                    detailView: {
+                        'dutyColor': '',
+                        'dutyType': '',
+                        'id': '',
+                        'month': '',
+                        'year': '',
+                        'day': '',
+                    },
                     batchEditMode: false,
                     isCreateScheduleMode: false,
                     calendarVisibility: "[[${member.calendarVisibility}]]",
@@ -575,6 +599,8 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                         content: '',
                         description: '',
                         startDateTime: '',
+                        startDate: '',
+                        startTime: '',
                         startDateTimeOld: '',
                         endDateTime: '',
                         visibility: 'FAMILY',
@@ -584,6 +610,8 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                         content: '',
                         description: '',
                         startDateTime: '',
+                        startDate: '',
+                        startTime: '',
                         startDateTimeOld: '',
                         endDateTime: '',
                         visibility: '',
@@ -802,16 +830,18 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                         app.monthSelector.year = app.year;
                     }
                     ,
-                    'createSchedule.startDateTime':
+                    'createSchedule.startTime':
                         function () {
+                            app.createSchedule.startDateTime = app.createSchedule.startDate + 'T' + app.createSchedule.startTime;
                             if (app.createSchedule.startDateTimeOld === app.createSchedule.endDateTime || app.createSchedule.startDateTime > app.createSchedule.endDateTime) {
                                 app.createSchedule.endDateTime = app.createSchedule.startDateTime;
                             }
                             app.createSchedule.startDateTimeOld = app.createSchedule.startDateTime;
                         }
                     ,
-                    'editingSchedule.startDateTime':
+                    'editingSchedule.startTime':
                         function () {
+                            app.editingSchedule.startDateTime = app.editingSchedule.startDate + 'T' + app.editingSchedule.startTime;
                             if (app.editingSchedule.startDateTimeOld === app.editingSchedule.endDateTime || app.editingSchedule.startDateTime > app.editingSchedule.endDateTime) {
                                 app.editingSchedule.endDateTime = app.editingSchedule.startDateTime;
                             }
@@ -1025,6 +1055,8 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                             content: '',
                             description: '',
                             startDateTime: app.formattedDateTime(app.detailView),
+                            startDate: app.formattedDate(app.detailView.year, app.detailView.month, app.detailView.day),
+                            startTime: '00:00',
                             endDateTime: app.formattedDateTime(app.detailView),
                             visibility: 'FAMILY',
                         }
@@ -1032,7 +1064,7 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                     ,
                     isDutyType(duty, dutyType) {
                         if (duty?.dutyType) {
-                            return dutyType.name == duty.dutyType
+                            return dutyType.name === duty.dutyType
                         }
                         return !dutyType.id
                     }
@@ -1063,14 +1095,12 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                                 });
                             }
                         })
-                    }
-                    ,
+                    },
                     formattedDateTime(duty) {
                         const month = duty.month.toString().padStart(2, '0');
                         const day = duty.day.toString().padStart(2, '0');
                         return `${duty.year}-${month}-${day}T00:00`;
-                    }
-                    ,
+                    },
                     scheduleCreateMode() {
                         app.isCreateScheduleMode = true;
                         const schedules = document.querySelector('#detail-view-modal .schedules');
@@ -1126,6 +1156,8 @@ <h5 class="modal-title" id="addModalLabel">할일 추가</h5>
                         app.editingSchedule.content = schedule.content;
                         app.editingSchedule.description = schedule.description;
                         app.editingSchedule.startDateTime = schedule.startDateTime;
+                        app.editingSchedule.startDate = schedule.startDateTime.split('T')[0];
+                        app.editingSchedule.startTime = schedule.startDateTime.split('T')[1];
                         app.editingSchedule.endDateTime = schedule.endDateTime;
                         app.editingSchedule.visibility = schedule.visibility;
                     }
diff --git a/src/main/resources/templates/layout/layout.html b/src/main/resources/templates/layout/layout.html
index 8111bdc0..455119dd 100644
--- a/src/main/resources/templates/layout/layout.html
+++ b/src/main/resources/templates/layout/layout.html
@@ -19,13 +19,22 @@
 <script>
     document.addEventListener('click', function (event) {
         const isClickInside = document.querySelector('.navbar-collapse').contains(event.target);
-        const isNavbarTogglerOpen = document.querySelector('.navbar-toggler').getAttribute('aria-expanded') == 'true';
+        const isNavbarTogglerOpen = document.querySelector('.navbar-toggler').getAttribute('aria-expanded') === 'true';
 
         if (!isClickInside && isNavbarTogglerOpen) {
             document.querySelector('.navbar-toggler').click();
         }
     });
 
+    // Prevent Blocked aria-hidden
+    document.addEventListener("DOMContentLoaded", function () {
+        document.addEventListener('hide.bs.modal', function () {
+            if (document.activeElement) {
+                document.activeElement.blur();
+            }
+        });
+    });
+
     document.querySelector('.navbar-header').addEventListener('click', function (event) {
         document.querySelector('.navbar-toggler').click();
     });
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
index 6e377127..bf56b81d 100644
--- a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingServiceTest.kt
@@ -11,14 +11,14 @@ import org.springframework.ai.openai.api.OpenAiApi
 import java.time.LocalDate
 
 
+@Disabled("External API test")
 class ScheduleTimeParsingServiceTest {
 
     private val apiKey = "PUT_KEY_HERE_for_external_integration_test"
     val service = makeService()
 
     @Test
-    @Disabled("External API test")
-    fun parseScheduleTime1() {
+    fun `parseScheduleTime guess night`() {
         val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
@@ -28,13 +28,13 @@ class ScheduleTimeParsingServiceTest {
 
         Assertions.assertThat(response.result).isTrue()
         Assertions.assertThat(response.hasTime).isTrue()
-        Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T23:00:00")
+        Assertions.assertThat(response.startDateTime).isEqualTo("2025-02-28T23:00:00")
+        Assertions.assertThat(response.endDateTime).isEqualTo("2025-02-28T23:00:00")
         Assertions.assertThat(response.content).doesNotContain("11시")
     }
 
     @Test
-    @Disabled("External API test")
-    fun parseScheduleTime2() {
+    fun `parseScheduleTime guess evening`() {
         val service = makeService()
         val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
@@ -44,13 +44,13 @@ class ScheduleTimeParsingServiceTest {
         )
         Assertions.assertThat(response.result).isTrue()
         Assertions.assertThat(response.hasTime).isTrue()
-        Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T17:00:00")
+        Assertions.assertThat(response.startDateTime).isEqualTo("2025-02-28T17:00:00")
+        Assertions.assertThat(response.endDateTime).isEqualTo("2025-02-28T17:00:00")
         Assertions.assertThat(response.content).doesNotContain("다섯시")
     }
 
     @Test
-    @Disabled("External API test")
-    fun parseScheduleTime3() {
+    fun `parseScheduleTime guess AM`() {
         val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
@@ -59,13 +59,13 @@ class ScheduleTimeParsingServiceTest {
         )
         Assertions.assertThat(response.result).isTrue()
         Assertions.assertThat(response.hasTime).isTrue()
-        Assertions.assertThat(response.dateTime).isEqualTo("2025-02-28T11:30:00")
+        Assertions.assertThat(response.startDateTime).isEqualTo("2025-02-28T11:30:00")
+        Assertions.assertThat(response.endDateTime).isEqualTo("2025-02-28T11:30:00")
         Assertions.assertThat(response.content).doesNotContain("11:30")
     }
 
     @Test
-    @Disabled("External API test")
-    fun parseScheduleTime4() {
+    fun `parseScheduleTime does not have time info`() {
         val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
@@ -74,13 +74,13 @@ class ScheduleTimeParsingServiceTest {
         )
         Assertions.assertThat(response.result).isTrue()
         Assertions.assertThat(response.hasTime).isFalse()
-        Assertions.assertThat(response.dateTime).isNull()
+        Assertions.assertThat(response.startDateTime).isNull()
+        Assertions.assertThat(response.endDateTime).isNull()
         Assertions.assertThat(response.content).isEqualTo("오사카 여행")
     }
 
     @Test
-    @Disabled("External API test")
-    fun parseScheduleTime5() {
+    fun `parseScheduleTime range`() {
         val response = service.parseScheduleTime(
             ScheduleTimeParsingRequest(
                 date = LocalDate.of(2025, 2, 28),
@@ -88,9 +88,41 @@ class ScheduleTimeParsingServiceTest {
             )
         )
         Assertions.assertThat(response.result).isTrue()
+        Assertions.assertThat(response.hasTime).isTrue()
+        Assertions.assertThat(response.startDateTime).isEqualTo("2025-02-28T14:00:00")
+        Assertions.assertThat(response.endDateTime).isEqualTo("2025-02-28T16:00:00")
+        Assertions.assertThat(response.content).doesNotContain("2시")
+        Assertions.assertThat(response.content).doesNotContain("4시")
+    }
+
+    @Test
+    fun `parseScheduleTime guess early morning`() {
+        val response = service.parseScheduleTime(
+            ScheduleTimeParsingRequest(
+                date = LocalDate.of(2025, 2, 28),
+                content = "등산 6시 출발"
+            )
+        )
+        Assertions.assertThat(response.result).isTrue()
+        Assertions.assertThat(response.hasTime).isTrue()
+        Assertions.assertThat(response.startDateTime).isEqualTo("2025-02-28T06:00:00")
+        Assertions.assertThat(response.endDateTime).isEqualTo("2025-02-28T06:00:00")
+        Assertions.assertThat(response.content).doesNotContain("5시")
+    }
+
+    @Test
+    fun `parseScheduleTime have too many time`() {
+        val response = service.parseScheduleTime(
+            ScheduleTimeParsingRequest(
+                date = LocalDate.of(2025, 2, 28),
+                content = "3시 4시 5시중에 대충 밥 먹자"
+            )
+        )
+        Assertions.assertThat(response.result).isFalse()
         Assertions.assertThat(response.hasTime).isFalse()
-        Assertions.assertThat(response.dateTime).isNull()
-        Assertions.assertThat(response.content).isEqualTo("2시")
+        Assertions.assertThat(response.startDateTime).isNull()
+        Assertions.assertThat(response.endDateTime).isNull()
+        Assertions.assertThat(response.content).isNull()
     }
 
     private fun makeService(): ScheduleTimeParsingService {

From 719a7749d12dd175deffbdaad6592aa1b4652160 Mon Sep 17 00:00:00 2001
From: shane <psh40963@naver.com>
Date: Mon, 3 Mar 2025 13:21:59 +0900
Subject: [PATCH 7/7] test: ScheduleTimeParsingQueueManager,
 ScheduleTimeParsingWorker

---
 .../schedule/domain/entity/Schedule.kt        |   2 +-
 .../ScheduleTimeParsingQueueManager.kt        |   4 +
 .../service/ScheduleTimeParsingWorker.kt      |   5 +-
 .../ScheduleTimeParsingQueueManagerTest.kt    |  77 ++++++++
 .../service/ScheduleTimeParsingWorkerTest.kt  | 180 ++++++++++++++++++
 5 files changed, 264 insertions(+), 4 deletions(-)
 create mode 100644 src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManagerTest.kt
 create mode 100644 src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorkerTest.kt

diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
index 334991b8..9a0feb29 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/domain/entity/Schedule.kt
@@ -26,7 +26,7 @@ class Schedule(
     var endDateTime: LocalDateTime,
 
     @Column(name = "position", nullable = false)
-    var position: Int,
+    var position: Int = -1,
 
     @Column(name = "visibility", nullable = false)
     @Enumerated(EnumType.STRING)
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
index 0d9b97c8..396d86d7 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManager.kt
@@ -103,4 +103,8 @@ class ScheduleTimeParsingQueueManager(
         }
     }
 
+    fun queueSize(): Int {
+        return queue.size
+    }
+
 }
diff --git a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
index 9b8ee6d6..21ba427c 100644
--- a/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
+++ b/src/main/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorker.kt
@@ -13,9 +13,6 @@ import java.time.LocalDate
 import java.time.LocalDateTime
 import java.time.format.DateTimeParseException
 
-/**
- * Do not use @Transaction dirty checking since it will be working on another thread.
- */
 @Service
 class ScheduleTimeParsingWorker(
     private val scheduleTimeParsingService: ScheduleTimeParsingService,
@@ -57,6 +54,8 @@ class ScheduleTimeParsingWorker(
             schedule.startDateTime = parsedStart
             schedule.endDateTime = parsedEnd
             schedule.contentWithoutTime = response.content ?: ""
+            
+            // Do not use JPA dirty checking since it will be working on another thread.
             scheduleRepository.save(schedule)
         } catch (e: DateTimeParseException) {
             log.warn("Failed to parse dateTime: $response")
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManagerTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManagerTest.kt
new file mode 100644
index 00000000..137f84d7
--- /dev/null
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingQueueManagerTest.kt
@@ -0,0 +1,77 @@
+package com.tistory.shanepark.dutypark.schedule.timeparsing.service
+
+import com.tistory.shanepark.dutypark.member.domain.entity.Member
+import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus.PARSED
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus.WAIT
+import com.tistory.shanepark.dutypark.schedule.repository.ScheduleRepository
+import org.junit.jupiter.api.Assertions.assertEquals
+import org.junit.jupiter.api.BeforeEach
+import org.junit.jupiter.api.Test
+import org.junit.jupiter.api.extension.ExtendWith
+import org.mockito.InjectMocks
+import org.mockito.Mock
+import org.mockito.Mockito.`when`
+import org.mockito.junit.jupiter.MockitoExtension
+import org.mockito.kotlin.times
+import org.mockito.kotlin.verify
+import java.time.LocalDateTime
+
+@ExtendWith(MockitoExtension::class)
+class ScheduleTimeParsingQueueManagerTest {
+
+    @Mock
+    lateinit var worker: ScheduleTimeParsingWorker
+
+    @Mock
+    lateinit var scheduleRepository: ScheduleRepository
+
+    @InjectMocks
+    lateinit var queueManager: ScheduleTimeParsingQueueManager
+
+    @BeforeEach
+    fun setUp() {
+        queueManager = ScheduleTimeParsingQueueManager(worker, scheduleRepository)
+    }
+
+    @Test
+    fun `init should load WAIT schedules into queue`() {
+        // Given
+        val schedules = listOf(
+            makeSchedule(),
+            makeSchedule(),
+        )
+        `when`(scheduleRepository.findAllByParsingTimeStatus(WAIT)).thenReturn(schedules)
+
+        // When
+        queueManager.init()
+
+        // Then
+        assertEquals(2, queueManager.queueSize())
+        verify(scheduleRepository, times(1)).findAllByParsingTimeStatus(WAIT)
+    }
+
+    @Test
+    fun `addTask should add only WAIT status tasks to queue`() {
+        // Given
+        val waitSchedule = makeSchedule()
+        val nonWaitSchedule = makeSchedule(PARSED)
+
+        // When
+        queueManager.addTask(waitSchedule)
+        queueManager.addTask(nonWaitSchedule)
+
+        // Then
+        assertEquals(1, queueManager.queueSize())
+    }
+
+    private fun makeSchedule(parsingTimeStatus: ParsingTimeStatus = WAIT): Schedule {
+        val now = LocalDateTime.now()
+        val member = Member("")
+        val schedule = Schedule(member = member, content = "", startDateTime = now, endDateTime = now)
+        schedule.parsingTimeStatus = parsingTimeStatus
+        return schedule
+    }
+
+}
diff --git a/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorkerTest.kt b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorkerTest.kt
new file mode 100644
index 00000000..a1dd2096
--- /dev/null
+++ b/src/test/kotlin/com/tistory/shanepark/dutypark/schedule/timeparsing/service/ScheduleTimeParsingWorkerTest.kt
@@ -0,0 +1,180 @@
+import com.tistory.shanepark.dutypark.member.domain.entity.Member
+import com.tistory.shanepark.dutypark.schedule.domain.entity.Schedule
+import com.tistory.shanepark.dutypark.schedule.domain.enums.ParsingTimeStatus
+import com.tistory.shanepark.dutypark.schedule.repository.ScheduleRepository
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingResponse
+import com.tistory.shanepark.dutypark.schedule.timeparsing.domain.ScheduleTimeParsingTask
+import com.tistory.shanepark.dutypark.schedule.timeparsing.service.ScheduleTimeParsingService
+import com.tistory.shanepark.dutypark.schedule.timeparsing.service.ScheduleTimeParsingWorker
+import org.assertj.core.api.Assertions.assertThat
+import org.junit.jupiter.api.Test
+import org.junit.jupiter.api.extension.ExtendWith
+import org.mockito.ArgumentMatchers.any
+import org.mockito.InjectMocks
+import org.mockito.Mock
+import org.mockito.Mockito.*
+import org.mockito.junit.jupiter.MockitoExtension
+import org.mockito.kotlin.anyOrNull
+import java.time.LocalDateTime
+import java.util.*
+
+@ExtendWith(MockitoExtension::class)
+class ScheduleTimeParsingWorkerTest {
+
+    @Mock
+    lateinit var scheduleTimeParsingService: ScheduleTimeParsingService
+
+    @Mock
+    lateinit var scheduleRepository: ScheduleRepository
+
+    @InjectMocks
+    lateinit var worker: ScheduleTimeParsingWorker
+
+    private fun createSchedule(): Schedule {
+        val randomDay = LocalDateTime.of(2025, 3, 3, 0, 0, 0, 0)
+        val member = Member("")
+        val schedule = Schedule(member = member, content = "", startDateTime = randomDay, endDateTime = randomDay)
+        return schedule
+    }
+
+    @Test
+    fun `if schedule is already deleted, never run`() {
+        // Given
+        val scheduleId = UUID.randomUUID()
+        val task = ScheduleTimeParsingTask(scheduleId = scheduleId)
+        `when`(scheduleRepository.findById(scheduleId)).thenReturn(Optional.empty())
+
+        // When
+        worker.run(task)
+
+        // Then
+        verify(scheduleRepository, never()).save(any())
+    }
+
+    @Test
+    fun `if the task is expired, skip`() {
+        // Given
+        val schedule = createSchedule()
+        schedule.lastModifiedDate = LocalDateTime.now().plusHours(1)
+        val task = ScheduleTimeParsingTask(scheduleId = schedule.id)
+        `when`(scheduleRepository.findById(schedule.id)).thenReturn(Optional.of(schedule))
+
+        // When
+        worker.run(task)
+
+        // Then
+        verify(scheduleRepository, never()).save(any())
+    }
+
+    @Test
+    fun `if time info already exists, it changes status into ALREADY_HAVE_TIME_INFO`() {
+        // Given
+        val schedule = createSchedule().apply {
+            startDateTime = LocalDateTime.of(2023, 3, 1, 10, 0)
+            endDateTime = LocalDateTime.of(2023, 3, 1, 11, 0)
+        }
+        val task = ScheduleTimeParsingTask(scheduleId = schedule.id)
+        `when`(scheduleRepository.findById(schedule.id)).thenReturn(Optional.of(schedule))
+
+        // When
+        worker.run(task)
+
+        // Then
+        assertThat(schedule.parsingTimeStatus).isEqualTo(ParsingTimeStatus.ALREADY_HAVE_TIME_INFO)
+        verify(scheduleRepository).save(schedule)
+    }
+
+    @Test
+    fun `if fail to parse, it changes status into FAILED`() {
+        // Given
+        val schedule = createSchedule()
+        val task = ScheduleTimeParsingTask(scheduleId = schedule.id)
+        `when`(scheduleRepository.findById(schedule.id)).thenReturn(Optional.of(schedule))
+        val response = ScheduleTimeParsingResponse(
+            result = false,
+        )
+        `when`(scheduleTimeParsingService.parseScheduleTime(anyOrNull())).thenReturn(response)
+
+        // When
+        worker.run(task)
+
+        // Then
+        assertThat(schedule.parsingTimeStatus).isEqualTo(ParsingTimeStatus.FAILED)
+        verify(scheduleRepository).save(schedule)
+    }
+
+    @Test
+    fun `If there is no time information, it changes status into NO_TIME_INFO`() {
+        // Given
+        val schedule = createSchedule()
+        val task = ScheduleTimeParsingTask(scheduleId = schedule.id)
+        `when`(scheduleRepository.findById(schedule.id)).thenReturn(Optional.of(schedule))
+        val response = ScheduleTimeParsingResponse(
+            result = true,
+            hasTime = false,
+        )
+        `when`(scheduleTimeParsingService.parseScheduleTime(anyOrNull())).thenReturn(response)
+
+        // When
+        worker.run(task)
+
+        // Then
+        assertThat(schedule.parsingTimeStatus).isEqualTo(ParsingTimeStatus.NO_TIME_INFO)
+        verify(scheduleRepository).save(schedule)
+    }
+
+    @Test
+    fun `When parsing is successful, it updates the schedule`() {
+        // Given
+        val schedule = createSchedule()
+        val task = ScheduleTimeParsingTask(scheduleId = schedule.id)
+        `when`(scheduleRepository.findById(schedule.id)).thenReturn(Optional.of(schedule))
+
+        val newStart = LocalDateTime.of(2023, 3, 1, 9, 0).toString()
+        val newEnd = LocalDateTime.of(2023, 3, 1, 10, 0).toString()
+        val response = ScheduleTimeParsingResponse(
+            result = true,
+            hasTime = true,
+            startDateTime = newStart,
+            endDateTime = newEnd,
+            content = "시간정보 제거된 내용"
+        )
+        `when`(scheduleTimeParsingService.parseScheduleTime(anyOrNull())).thenReturn(response)
+
+        // When
+        worker.run(task)
+
+        // Then
+        assertThat(schedule.parsingTimeStatus).isEqualTo(ParsingTimeStatus.PARSED)
+        assertThat(schedule.startDateTime).isEqualTo(newStart)
+        assertThat(schedule.endDateTime).isEqualTo(newEnd)
+        assertThat(schedule.contentWithoutTime).isEqualTo("시간정보 제거된 내용")
+
+        verify(scheduleRepository).save(schedule)
+    }
+
+    @Test
+    fun `if date is not parsable and DateTimeParseException is thrown, it changes status into FAILED`() {
+        // Given
+        val schedule = createSchedule()
+        val task = ScheduleTimeParsingTask(scheduleId = schedule.id)
+        `when`(scheduleRepository.findById(schedule.id)).thenReturn(Optional.of(schedule))
+
+        `when`(scheduleTimeParsingService.parseScheduleTime(anyOrNull())).thenReturn(
+            ScheduleTimeParsingResponse(
+                result = true,
+                hasTime = true,
+                startDateTime = "can not parse date",
+                endDateTime = "not parseable date",
+            )
+        )
+
+        // When
+        worker.run(task)
+
+        // Then
+        assertThat(schedule.parsingTimeStatus).isEqualTo(ParsingTimeStatus.FAILED)
+        verify(scheduleRepository).save(schedule)
+    }
+
+}