diff --git a/datadog_checks_dev/hatch.toml b/datadog_checks_dev/hatch.toml
index 809fa9273f3c3..e4e3ffa2cf4c9 100644
--- a/datadog_checks_dev/hatch.toml
+++ b/datadog_checks_dev/hatch.toml
@@ -7,10 +7,6 @@ mypy-args = [
   "datadog_checks/dev/tooling/commands/release/trello/testable.py",
   "datadog_checks/dev/tooling/commands/release/trello/status.py",
 ]
-# TODO remove once https://github.com/pallets/click/issues/2558 is solved
-mypy-deps = [
-  "click~=8.1,!=8.1.4",
-]
 
 [envs.default]
 e2e-env = false
diff --git a/datadog_checks_dev/pyproject.toml b/datadog_checks_dev/pyproject.toml
index 609c71f68bf6c..17c14abcfce56 100644
--- a/datadog_checks_dev/pyproject.toml
+++ b/datadog_checks_dev/pyproject.toml
@@ -63,8 +63,7 @@ cli = [
     "atomicwrites",
     "beautifulsoup4>=4.9.3",
     "build>=0.7.0",
-    # TODO remove when https://github.com/pallets/click/issues/2558 is solved and unpin the version in the hatch files for ddev and datadog_checks_dev
-    "click~=8.1,!=8.1.4",
+    "click~=8.1.6",
     "codespell",
     "colorama",
     "datamodel-code-generator~=0.21.1",
diff --git a/ddev/hatch.toml b/ddev/hatch.toml
index 60c7db65736e3..174ef100f206d 100644
--- a/ddev/hatch.toml
+++ b/ddev/hatch.toml
@@ -3,10 +3,6 @@ check-types = true
 mypy-args = [
   "src/ddev",
 ]
-# TODO remove once https://github.com/pallets/click/issues/2558 is solved
-mypy-deps = [
-  "click~=8.1,!=8.1.4",
-]
 
 [envs.default]
 python = "3.9"
diff --git a/ddev/pyproject.toml b/ddev/pyproject.toml
index 05bf1f2c42f17..62e575a126934 100644
--- a/ddev/pyproject.toml
+++ b/ddev/pyproject.toml
@@ -26,6 +26,7 @@ classifiers = [
     "Programming Language :: Python :: 3.9",
 ]
 dependencies = [
+    "click~=8.1.6",
     "datadog-checks-dev[cli]~=22.0",
     "hatch>=1.6.3",
     "httpx",