diff --git a/agent-container.py b/agent-container.py
index 2c06fe7..ba76ea3 100755
--- a/agent-container.py
+++ b/agent-container.py
@@ -161,6 +161,12 @@ class AgentContainer:
         if not self.image_exists():
             self.build_image()
 
+        if self.container_exists() and not self._container_image_matches():
+            logger.info(
+                "Recreating container: it was created from an outdated image"
+            )
+            self.remove_container()
+
         if not self.container_exists():
             self.create_container()
 
@@ -392,6 +398,24 @@ class AgentContainer:
             ]
         )
 
+    def _container_image_matches(self) -> bool:
+        """Whether the existing container was created from the current image.
+
+        After an image rebuild the old container keeps running the stale
+        image, so tools baked into previous builds (or missing from new
+        ones) linger. Comparing image IDs catches that."""
+        container_image = subprocess.run(
+            ["docker", "container", "inspect", "-f", "{{.Image}}", self.container_name],
+            capture_output=True,
+            text=True,
+        ).stdout.strip()
+        current_image = subprocess.run(
+            ["docker", "image", "inspect", "-f", "{{.Id}}", self.IMAGE],
+            capture_output=True,
+            text=True,
+        ).stdout.strip()
+        return bool(container_image) and container_image == current_image
+
     def start_container(self) -> bool:
         subprocess.run(
             ["docker", "start", self.container_name],