diff --git a/ddev/CHANGELOG.md b/ddev/CHANGELOG.md
index a4d192f7e831c..66000a2e0333d 100644
--- a/ddev/CHANGELOG.md
+++ b/ddev/CHANGELOG.md
@@ -5,6 +5,7 @@
 ***Added***:
 
 * Migrate E2E features ([#15931](https://github.com/DataDog/integrations-core/pull/15931))
+* Bump the minimum supported version of datadog-checks-dev ([#16006](https://github.com/DataDog/integrations-core/pull/16006))
 
 ## 5.1.1 / 2023-09-29
 
diff --git a/ddev/pyproject.toml b/ddev/pyproject.toml
index b3871b3dbe0c2..27bf44abfd8f6 100644
--- a/ddev/pyproject.toml
+++ b/ddev/pyproject.toml
@@ -28,7 +28,7 @@ classifiers = [
 dependencies = [
     "click~=8.1.6",
     "coverage",
-    "datadog-checks-dev[cli]>=25.1.2,<26",
+    "datadog-checks-dev[cli]~=27.0",
     "hatch>=1.6.3",
     "httpx",
     "jsonpointer",
diff --git a/ddev/src/ddev/e2e/agent/docker.py b/ddev/src/ddev/e2e/agent/docker.py
index a508e0d5c7f3f..30e8e2a0effe6 100644
--- a/ddev/src/ddev/e2e/agent/docker.py
+++ b/ddev/src/ddev/e2e/agent/docker.py
@@ -162,7 +162,7 @@ def start(self, *, agent_build: str, local_packages: dict[Path, str], env_vars:
                     remaining = ':'.join(parts[2:])
                     volumes[i] = f'/{vm_file}:{remaining}'
 
-        if not os.getenv('DDEV_E2E_DOCKER_NO_PULL') != '1':
+        if os.getenv('DDEV_E2E_DOCKER_NO_PULL') != '1':
             process = self._run_command(['docker', 'pull', agent_build])
             if process.returncode:
                 raise RuntimeError(f'Could not pull image {agent_build}')