diff --git a/.github/ISSUE_TEMPLATE/bug.yml b/.github/ISSUE_TEMPLATE/bug.yml
index 8432d2f92..fdee895b8 100644
--- a/.github/ISSUE_TEMPLATE/bug.yml
+++ b/.github/ISSUE_TEMPLATE/bug.yml
@@ -15,7 +15,7 @@ body:
     attributes:
       label: Singer SDK Version
       description: Version of the library you are using
-      placeholder: "0.44.1"
+      placeholder: "0.44.2"
     validations:
       required: true
   - type: checkboxes
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 52d6a75e9..3e60d4c28 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,14 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## v0.44.2 (2025-01-31)
+
+### 📦 Packaging changes
+
+- [#2854](https://github.com/meltano/sdk/issues/2854) Use PEP 639
+- [#2852](https://github.com/meltano/sdk/issues/2852) Remove `urllib3` constraint
+- [#2851](https://github.com/meltano/sdk/issues/2851) Use uv to manage this project
+
 ## v0.44.1 (2025-01-29)
 
 ### 🐛 Fixes
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
index b2a7ce578..b1f384118 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
@@ -36,12 +36,12 @@ packages = [
 {%- endif %}
 
 [tool.poetry.dependencies]
-singer-sdk = { version="~=0.44.1"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
+singer-sdk = { version="~=0.44.2"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
 fs-s3fs = { version = "~=1.1.1", optional = true }
 
 [tool.poetry.group.dev.dependencies]
 pytest = ">=8"
-singer-sdk = { version="~=0.44.1", extras = ["testing"] }
+singer-sdk = { version="~=0.44.2", extras = ["testing"] }
 
 [tool.poetry.extras]
 s3 = ["fs-s3fs"]
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
index f376111e4..56b55eafc 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
@@ -35,7 +35,7 @@ packages = [
 {%- endif %}
 
 [tool.poetry.dependencies]
-singer-sdk = { version="~=0.44.1", extras = [
+singer-sdk = { version="~=0.44.2", extras = [
     {%- if cookiecutter.auth_method == "JWT" -%}"jwt", {% endif -%}
     {%- if cookiecutter.faker_extra -%}"faker",{%- endif -%}
 ] }
@@ -50,9 +50,9 @@ sqlalchemy = "~=2.0.36"
 [tool.poetry.group.dev.dependencies]
 pytest = ">=8"
 {%- if cookiecutter.auth_method == "JWT" %}
-singer-sdk = { version="~=0.44.1", extras = ["jwt", "testing"] }
+singer-sdk = { version="~=0.44.2", extras = ["jwt", "testing"] }
 {%- else %}
-singer-sdk = { version="~=0.44.1", extras = ["testing"] }
+singer-sdk = { version="~=0.44.2", extras = ["testing"] }
 {%- endif %}
 
 [tool.poetry.extras]
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
index 8975b9a99..3b747cfec 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
@@ -35,7 +35,7 @@ packages = [
 {%- endif %}
 
 [tool.poetry.dependencies]
-singer-sdk = { version="~=0.44.1"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
+singer-sdk = { version="~=0.44.2"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
 fs-s3fs = { version = "~=1.1.1", optional = true }
 {%- if cookiecutter.serialization_method != "SQL" %}
 requests = "~=2.32.3"
@@ -43,7 +43,7 @@ requests = "~=2.32.3"
 
 [tool.poetry.dev-dependencies]
 pytest = ">=8"
-singer-sdk = { version="~=0.44.1", extras = ["testing"] }
+singer-sdk = { version="~=0.44.2", extras = ["testing"] }
 
 [tool.poetry.extras]
 s3 = ["fs-s3fs"]
diff --git a/docs/conf.py b/docs/conf.py
index 9b2d437b4..fe0a41f92 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -29,7 +29,7 @@
 author = "Meltano Core Team and Contributors"
 
 # The full version, including alpha/beta/rc tags
-release = "0.44.1"
+release = "0.44.2"
 
 
 # -- General configuration -------------------------------------------------------------
diff --git a/pyproject.toml b/pyproject.toml
index 17b999d22..f8816bc43 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -180,7 +180,7 @@ xfail_strict = false
 
 [tool.commitizen]
 name = "cz_version_bump"
-version = "0.44.1"
+version = "0.44.2"
 changelog_merge_prerelease = true
 prerelease_offset = 1
 tag_format = "v$major.$minor.$patch$prerelease"