diff --git a/.circleci/config.yml b/.circleci/config.yml
index 7f63bd7a3569b..786946b5182e6 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -59,6 +59,9 @@ parameters:
   sync_test_op_node_dispatch:
     type: boolean
     default: false
+  ai_contracts_test_dispatch:
+    type: boolean
+    default: false
   github-event-type:
     type: string
     default: "__not_set__"
@@ -985,6 +988,28 @@ jobs:
             - "/root/.cache/go-build"
       - notify-failures-on-develop
 
+  # AI Contracts Test Maintenance System
+  # Runbook: https://github.com/ethereum-optimism/optimism/blob/develop/ops/ai-eng/contracts-test-maintenance/docs/runbook.md
+  ai-contracts-test:
+    circleci_ip_ranges: true
+    docker:
+      - image: <<pipeline.parameters.default_docker_image>>
+    resource_class: xlarge
+    steps:
+      - checkout-from-workspace
+      - run:
+          name: Check Python version
+          command: python3 --version
+      - run:
+          name: Run AI Contracts Test System
+          command: just ai-contracts-test
+          working_directory: ops/ai-eng
+          no_output_timeout: 60m
+      - store_artifacts:
+          path: ops/ai-eng/contracts-test-maintenance/log.jsonl
+          destination: log.jsonl
+      - notify-failures-on-develop
+
   contracts-bedrock-coverage:
     circleci_ip_ranges: true
     docker:
@@ -3074,3 +3099,17 @@ workflows:
           context:
             - circleci-repo-readonly-authenticated-github-token
             - oplabs-tools-data-public-metrics-bucket
+
+  ai-contracts-test-workflow:
+    when:
+      equal: [true, << pipeline.parameters.ai_contracts_test_dispatch >>]
+    jobs:
+      - initialize:
+          context:
+            - circleci-repo-readonly-authenticated-github-token
+      - ai-contracts-test:
+          context:
+            - circleci-repo-readonly-authenticated-github-token
+            - devin-api
+          requires:
+            - initialize
diff --git a/ops/ai-eng/contracts-test-maintenance/VERSION b/ops/ai-eng/contracts-test-maintenance/VERSION
index a2268e2de4458..d15723fbe8de3 100644
--- a/ops/ai-eng/contracts-test-maintenance/VERSION
+++ b/ops/ai-eng/contracts-test-maintenance/VERSION
@@ -1 +1 @@
-0.3.1
\ No newline at end of file
+0.3.2
diff --git a/ops/ai-eng/contracts-test-maintenance/components/devin-api/devin_client.py b/ops/ai-eng/contracts-test-maintenance/components/devin-api/devin_client.py
index 8623076e9194a..d30a716b9b9dd 100644
--- a/ops/ai-eng/contracts-test-maintenance/components/devin-api/devin_client.py
+++ b/ops/ai-eng/contracts-test-maintenance/components/devin-api/devin_client.py
@@ -105,6 +105,9 @@ def _make_request(url, headers, data=None, method="GET"):
             print(f"Request failed: {method} {url}")
             print(f"Error: {e}")
             raise
+    except TimeoutError as e:
+        print(f"Request timeout - will retry")
+        return None
     except Exception as e:
         print(f"Request failed: {method} {url}")
         print(f"Error: {e}")