diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
index a71071521..7fad53cd1 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
@@ -49,8 +49,14 @@ s3 = [
 
 [dependency-groups]
 dev = [
+    { include-group = "test" },
+]
+test = [
     "pytest>=8",
-    "singer-sdk[testing]~=0.44.3",
+    {%- if cookiecutter.include_ci_files == "GitHub" %}
+    "pytest-github-actions-annotate-failures>=0.3",
+    {%- endif %}
+    "singer-sdk[testing]",
 ]
 
 {%- if cookiecutter.variant != "None (Skip)" %}
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
index 632c513b0..8e6fe0032 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
@@ -2,13 +2,14 @@
 
 [tox]
 envlist = py3{9,10,11,12,13}
+minversion = 4.22
 requires =
-    tox>=4.19
+    tox>=4.22
 
 [testenv]
 pass_env =
     {{cookiecutter.mapper_id.replace('-', '_').upper()}}_*
-deps =
-    pytest
+dependency_groups =
+    test
 commands =
     pytest {posargs}
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
index cd112255a..371845264 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
@@ -58,8 +58,14 @@ s3 = [
 
 [dependency-groups]
 dev = [
+    { include-group = "test" },
+]
+test = [
     "pytest>=8",
-    "singer-sdk[testing]~=0.44.3",
+    {%- if cookiecutter.include_ci_files == "GitHub" %}
+    "pytest-github-actions-annotate-failures>=0.3",
+    {%- endif %}
+    "singer-sdk[testing]",
 ]
 
 {%- if cookiecutter.variant != "None (Skip)" %}
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
index 18cf562e1..628dc4f23 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
@@ -2,13 +2,14 @@
 
 [tox]
 envlist = py3{9,10,11,12,13}
+minversion = 4.22
 requires =
-    tox>=4.19
+    tox>=4.22
 
 [testenv]
 pass_env =
     {{cookiecutter.tap_id.replace('-', '_').upper()}}_*
-deps =
-    pytest
+dependency_groups =
+    test
 commands =
     pytest {posargs}
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
index 2128c8d1d..622d1d76b 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
@@ -51,8 +51,14 @@ s3 = [
 
 [dependency-groups]
 dev = [
+    { include-group = "test" },
+]
+test = [
     "pytest>=8",
-    "singer-sdk[testing]~=0.44.3",
+    {%- if cookiecutter.include_ci_files == "GitHub" %}
+    "pytest-github-actions-annotate-failures>=0.3",
+    {%- endif %}
+    "singer-sdk[testing]",
 ]
 
 {%- if cookiecutter.variant != "None (Skip)" %}
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini b/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
index 82cea9e62..11cea93b6 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
@@ -2,13 +2,14 @@
 
 [tox]
 envlist = py3{9,10,11,12,13}
+minversion = 4.22
 requires =
-    tox>=4.19
+    tox>=4.22
 
 [testenv]
 pass_env =
     {{cookiecutter.target_id.replace('-', '_').upper()}}_*
-deps =
-    pytest
+dependency_groups =
+    test
 commands =
     pytest {posargs}