diff --git a/crates/goose-cli/src/prompt.rs b/crates/goose-cli/src/prompt.rs
index 79d7ae58c..a45933ecc 100644
--- a/crates/goose-cli/src/prompt.rs
+++ b/crates/goose-cli/src/prompt.rs
@@ -19,6 +19,7 @@ pub trait Prompt {
         println!("Goose is running! Enter your instructions, or try asking what goose can do.");
         println!("\n");
     }
+    fn ask_user_for_truncation(&self) -> Result<Input>; // Pd8b8
 }
 
 pub struct Input {
@@ -30,10 +31,5 @@ pub enum InputType {
     AskAgain, // Ask the user for input again. Control flow command.
     Message,  // User sent a message
     Exit,     // User wants to exit the session
-}
-
-pub enum Theme {
-    Light,
-    Dark,
-    Ansi, // Use terminal's ANSI/base16 colors directly.
+    TruncateFurther, // P3abf
 }
diff --git a/crates/goose/src/agents/extension.rs b/crates/goose/src/agents/extension.rs
index db5d5f3bc..4a1c739f2 100644
--- a/crates/goose/src/agents/extension.rs
+++ b/crates/goose/src/agents/extension.rs
@@ -11,7 +11,7 @@ pub enum ExtensionError {
     Initialization(ExtensionConfig, ClientError),
     #[error("Failed a client call to an MCP server: {0}")]
     Client(#[from] ClientError),
-    #[error("User Message exceeded context-limit. History could not be truncated to accomodate.")]
+    #[error("User Message exceeded context-limit. History could not be truncated to accomodate. Please choose to either attempt further truncation or exit.")]
     ContextLimit,
     #[error("Transport error: {0}")]
     Transport(#[from] mcp_client::transport::Error),
diff --git a/crates/goose/tests/providers.rs b/crates/goose/tests/providers.rs
index 332f3ee76..f7e17ad6d 100644
--- a/crates/goose/tests/providers.rs
+++ b/crates/goose/tests/providers.rs
@@ -253,11 +253,71 @@ impl ProviderTester {
         Ok(())
     }
 
+    async fn test_user_prompt_on_context_length_exceeded(&self) -> Result<()> { // P91ef
+        // Simulate a scenario where context length is exceeded and user is prompted
+        let large_message_content = "hello ".repeat(300_000);
+
+        let messages = vec![
+            Message::user().with_text("hi there. what is 2 + 2?"),
+            Message::assistant().with_text("hey! I think it's 4."),
+            Message::user().with_text(&large_message_content),
+            Message::assistant().with_text("heyy!!"),
+            Message::user().with_text("what's the meaning of life?"),
+            Message::assistant().with_text("the meaning of life is 42"),
+            Message::user().with_text(
+                "did I ask you what's 2+2 in this message history? just respond with 'yes' or 'no'",
+            ),
+        ];
+
+        // Test that we get ProviderError::ContextLengthExceeded when the context window is exceeded
+        let result = self
+            .provider
+            .complete("You are a helpful assistant.", &messages, &[])
+            .await;
+
+        // Print some debug info
+        println!("=== {}::user_prompt_on_context_length_exceeded ===", self.name);
+        dbg!(&result);
+        println!("===================");
+
+        // Verify that the user is prompted for further action
+        assert!(
+            result.is_err(),
+            "Expected error when context window is exceeded"
+        );
+        assert!(
+            matches!(result.unwrap_err(), ProviderError::ContextLengthExceeded(_)),
+            "Expected error to be ContextLengthExceeded"
+        );
+
+        // Simulate user choosing to attempt further truncation
+        let user_input = Message::user().with_text("Attempt further truncation");
+
+        let result = self
+            .provider
+            .complete("You are a helpful assistant.", &[user_input], &[])
+            .await;
+
+        // Print some debug info
+        println!("=== {}::user_prompt_on_context_length_exceeded_further_truncation ===", self.name);
+        dbg!(&result);
+        println!("===================");
+
+        // Verify that the system continues truncation with a further reduced context limit
+        assert!(
+            result.is_ok(),
+            "Expected success after user chooses to attempt further truncation"
+        );
+
+        Ok(())
+    }
+
     /// Run all provider tests
     async fn run_test_suite(&self) -> Result<()> {
         self.test_basic_response().await?;
         self.test_tool_usage().await?;
         self.test_context_length_exceeded_error().await?;
+        self.test_user_prompt_on_context_length_exceeded().await?; // P91ef
         Ok(())
     }
 }