diff --git a/python_modules/dagster-test/dagster_test/test_project/test_jobs/repo.py b/python_modules/dagster-test/dagster_test/test_project/test_jobs/repo.py
index 4307a3c237fe2..9440bee4d18c8 100644
--- a/python_modules/dagster-test/dagster_test/test_project/test_jobs/repo.py
+++ b/python_modules/dagster-test/dagster_test/test_project/test_jobs/repo.py
@@ -31,6 +31,7 @@
 from dagster._core.definitions.job_definition import JobDefinition
 from dagster._core.definitions.output import Out
 from dagster._core.definitions.resource_definition import ResourceDefinition
+from dagster._core.errors import DagsterExecutionInterruptedError
 from dagster._core.execution.plan.objects import StepSuccessData
 from dagster._core.test_utils import nesting_graph, poll_for_step_start
 from dagster._utils import segfault
@@ -175,10 +176,18 @@ def demo_slow_graph():
     count_letters(multiply_the_word_slow())
 
 
-@op
-def hanging_op(_):
-    while True:
-        time.sleep(0.1)
+@op(config_schema={"cleanup_delay": Field(int, is_required=False)})
+def hanging_op(context):
+    try:
+        while True:
+            time.sleep(0.1)
+    except DagsterExecutionInterruptedError:
+        cleanup_delay = context.op_config.get("cleanup_delay")
+        if cleanup_delay:
+            context.log.info(f"Delaying cleanup for {cleanup_delay} seconds")
+            time.sleep(cleanup_delay)
+            context.log.info("Done cleaning up")
+        raise
 
 
 @op(config_schema={"looking_for": str})
diff --git a/python_modules/libraries/dagster-docker/dagster_docker/docker_executor.py b/python_modules/libraries/dagster-docker/dagster_docker/docker_executor.py
index 608ede06330f7..ab60303b0f8a7 100644
--- a/python_modules/libraries/dagster-docker/dagster_docker/docker_executor.py
+++ b/python_modules/libraries/dagster-docker/dagster_docker/docker_executor.py
@@ -203,6 +203,12 @@ def _create_step_container(
         assert len(step_keys_to_execute) == 1, "Launching multiple steps is not currently supported"
         step_key = step_keys_to_execute[0]
 
+        container_kwargs = {**container_context.container_kwargs}
+        if "stop_timeout" in container_kwargs:
+            # This should work, but does not due to https://github.com/docker/docker-py/issues/3168
+            # Pull it out and apply it in the terminate() method instead
+            del container_kwargs["stop_timeout"]
+
         env_vars = dict([parse_env_var(env_var) for env_var in container_context.env_vars])
         env_vars["DAGSTER_RUN_JOB_NAME"] = step_handler_context.dagster_run.job_name
         env_vars["DAGSTER_RUN_STEP_KEY"] = step_key
@@ -213,7 +219,7 @@ def _create_step_container(
             network=container_context.networks[0] if len(container_context.networks) else None,
             command=execute_step_args.get_command_args(),
             environment=env_vars,
-            **container_context.container_kwargs,
+            **container_kwargs,
         )
 
     def launch_step(self, step_handler_context: StepHandlerContext) -> Iterator[DagsterEvent]:
@@ -311,4 +317,6 @@ def terminate_step(self, step_handler_context: StepHandlerContext) -> Iterator[D
 
         container = client.containers.get(container_name)
 
-        container.stop()
+        stop_timeout = container_context.container_kwargs.get("stop_timeout")
+
+        container.stop(timeout=stop_timeout)
diff --git a/python_modules/libraries/dagster-docker/dagster_docker/docker_run_launcher.py b/python_modules/libraries/dagster-docker/dagster_docker/docker_run_launcher.py
index 64630843fb12f..ad2b5ca3f822b 100644
--- a/python_modules/libraries/dagster-docker/dagster_docker/docker_run_launcher.py
+++ b/python_modules/libraries/dagster-docker/dagster_docker/docker_run_launcher.py
@@ -105,6 +105,12 @@ def _launch_container_with_command(self, run, docker_image, command):
 
         container_kwargs = {**container_context.container_kwargs}
         labels = container_kwargs.pop("labels", {})
+
+        if "stop_timeout" in container_kwargs:
+            # This should work, but does not due to https://github.com/docker/docker-py/issues/3168
+            # Pull it out and apply it in the terminate() method instead
+            del container_kwargs["stop_timeout"]
+
         if isinstance(labels, list):
             labels = {key: "" for key in labels}
 
@@ -208,6 +214,9 @@ def terminate(self, run_id):
 
         container = self._get_container(run)
 
+        container_context = self.get_container_context(run)
+        stop_timeout = container_context.container_kwargs.get("stop_timeout")
+
         if not container:
             self._instance.report_engine_event(
                 message="Unable to get docker container to send termination request to.",
@@ -216,7 +225,7 @@ def terminate(self, run_id):
             )
             return False
 
-        container.stop()
+        container.stop(timeout=stop_timeout)
 
         return True
 
diff --git a/python_modules/libraries/dagster-docker/dagster_docker_tests/test_launch_docker.py b/python_modules/libraries/dagster-docker/dagster_docker_tests/test_launch_docker.py
index c5c780beef93d..d73208450dd98 100644
--- a/python_modules/libraries/dagster-docker/dagster_docker_tests/test_launch_docker.py
+++ b/python_modules/libraries/dagster-docker/dagster_docker_tests/test_launch_docker.py
@@ -192,6 +192,7 @@ def test_terminate_launched_docker_run(aws_env):
     launcher_config = {
         "env_vars": aws_env,
         "network": "container:test-postgres-db-docker",
+        "container_kwargs": {"stop_timeout": 15},
     }
 
     if IS_BUILDKITE:
@@ -199,11 +200,14 @@ def test_terminate_launched_docker_run(aws_env):
     else:
         find_local_test_image(docker_image)
 
-    run_config = merge_yamls(
-        [
-            os.path.join(get_test_project_environments_path(), "env_s3.yaml"),
-        ]
-    )
+    run_config = {
+        **merge_yamls(
+            [
+                os.path.join(get_test_project_environments_path(), "env_s3.yaml"),
+            ]
+        ),
+        "ops": {"hanging_op": {"config": {"cleanup_delay": 10}}},
+    }
 
     with docker_postgres_instance(
         overrides={