diff --git a/features/k8s_helm_chart.feature b/features/k8s_helm_chart.feature
index 551577ed2..f7c732148 100644
--- a/features/k8s_helm_chart.feature
+++ b/features/k8s_helm_chart.feature
@@ -131,6 +131,14 @@ Feature: Kubernetes Helm Chart Structure
     When I read the server Dockerfile
     Then it should not use unpinned uv latest tag
 
+  Scenario: Server Dockerfile uses python -m cleveragents as ENTRYPOINT
+    When I read the server Dockerfile
+    Then the ENTRYPOINT should use "python -m cleveragents"
+
+  Scenario: Server Dockerfile CMD uses server serve subcommand
+    When I read the server Dockerfile
+    Then the CMD should include "server" and "serve"
+
   # -- Secrets structure --
 
   Scenario: Secrets template guards database secret with existingSecret check
diff --git a/features/steps/k8s_helm_chart_steps.py b/features/steps/k8s_helm_chart_steps.py
index df5588569..daaec178a 100644
--- a/features/steps/k8s_helm_chart_steps.py
+++ b/features/steps/k8s_helm_chart_steps.py
@@ -353,6 +353,35 @@ def step_dockerfile_removes_uv(context: Context) -> None:
     )
 
 
+@then('the ENTRYPOINT should use "{entrypoint}"')
+def step_dockerfile_entrypoint(context: Context, entrypoint: str) -> None:
+    """Assert that the Dockerfile ENTRYPOINT contains the expected command."""
+    pattern: re.Pattern[str] = re.compile(r"^ENTRYPOINT\s+\[.*\]", re.MULTILINE)
+    match = pattern.search(context.dockerfile_content)
+    assert match is not None, "Dockerfile.server is missing an ENTRYPOINT instruction"
+    entrypoint_line = match.group(0)
+    # Verify each token of the expected entrypoint appears in the ENTRYPOINT line
+    for token in entrypoint.split():
+        assert token in entrypoint_line, (
+            f"Expected ENTRYPOINT to contain '{token}', but got: {entrypoint_line!r}"
+        )
+
+
+@then('the CMD should include "{cmd_a}" and "{cmd_b}"')
+def step_dockerfile_cmd_includes(context: Context, cmd_a: str, cmd_b: str) -> None:
+    """Assert that the Dockerfile CMD contains the expected subcommand tokens."""
+    pattern: re.Pattern[str] = re.compile(r"^CMD\s+\[.*\]", re.MULTILINE)
+    match = pattern.search(context.dockerfile_content)
+    assert match is not None, "Dockerfile.server is missing a CMD instruction"
+    cmd_line = match.group(0)
+    assert cmd_a in cmd_line, (
+        f"Expected CMD to contain '{cmd_a}', but got: {cmd_line!r}"
+    )
+    assert cmd_b in cmd_line, (
+        f"Expected CMD to contain '{cmd_b}', but got: {cmd_line!r}"
+    )
+
+
 @when("I read the deployment README")
 def step_read_deployment_readme(context: Context) -> None:
     readme_path: Path = context.project_root / "k8s" / "README.md"