diff --git a/tests/gateway_workflow_integration.rs b/tests/gateway_workflow_integration.rs
index edf7de91..372cfdf8 100644
--- a/tests/gateway_workflow_integration.rs
+++ b/tests/gateway_workflow_integration.rs
@@ -30,15 +30,11 @@ mod tests {
                         "name": "wf-ci-webhook-demo",
                         "description": "CI webhook workflow demo",
                         "trigger_type": "system_event",
-                        "trigger": {
-                            "source": "github",
-                            "event_type": "issue.opened",
-                            "filters": {"repository": "nearai/ironclaw"}
-                        },
+                        "event_source": "github",
+                        "event_type": "issue.opened",
+                        "event_filters": {"repository": "nearai/ironclaw"},
                         "action_type": "lightweight",
-                        "action": {
-                            "prompt": "Summarize webhook and report issue number"
-                        }
+                        "prompt": "Summarize webhook and report issue number"
                     }),
                 )]),
             ))
@@ -69,6 +65,30 @@ mod tests {
         harness
             .send_chat(&thread_id, "create workflow routine")
             .await;
+        harness
+            .wait_for_turns(&thread_id, 1, Duration::from_secs(10))
+            .await;
+
+        let mut routine = None;
+        for _ in 0..30 {
+            routine = harness.routine_by_name("wf-ci-webhook-demo").await;
+            if routine.is_some() {
+                break;
+            }
+            tokio::time::sleep(Duration::from_millis(100)).await;
+        }
+        let routine = if let Some(r) = routine {
+            r
+        } else {
+            let history_dbg = harness.history(&thread_id).await;
+            let started_dbg = harness.test_channel.tool_calls_started();
+            let requests_dbg = mock.requests().await;
+            panic!(
+                "routine not created; tool_calls_started={started_dbg:?}; history={history_dbg}; mock_requests={requests_dbg:?}"
+            );
+        };
+        let routine_id = routine["id"].as_str().expect("routine id missing");
+
         harness.send_chat(&thread_id, "emit webhook event").await;
 
         let history = harness
@@ -77,12 +97,6 @@ mod tests {
         let turns = history["turns"].as_array().expect("turns array missing");
         assert!(turns.len() >= 2, "expected at least 2 turns");
 
-        let routine = harness
-            .routine_by_name("wf-ci-webhook-demo")
-            .await
-            .expect("routine not created");
-        let routine_id = routine["id"].as_str().expect("routine id missing");
-
         let runs_before = harness.routine_runs(routine_id).await;
         let before_count = runs_before["runs"]
             .as_array()
diff --git a/tests/support/gateway_workflow_harness.rs b/tests/support/gateway_workflow_harness.rs
index 77d53ac1..a1563f0e 100644
--- a/tests/support/gateway_workflow_harness.rs
+++ b/tests/support/gateway_workflow_harness.rs
@@ -17,8 +17,7 @@ use ironclaw::channels::web::server::{GatewayState, RateLimiter, start_server};
 use ironclaw::channels::web::sse::SseManager;
 use ironclaw::channels::web::ws::WsConnectionTracker;
 use ironclaw::channels::{Channel, IncomingMessage, MessageStream};
-use ironclaw::config::llm::RegistryProviderConfig;
-use ironclaw::config::{Config, RoutineConfig};
+use ironclaw::config::{Config, RegistryProviderConfig, RoutineConfig};
 use ironclaw::context::ContextManager;
 use ironclaw::db::Database;
 use ironclaw::db::libsql::LibSqlBackend;
diff --git a/tests/support/mock_openai_server.rs b/tests/support/mock_openai_server.rs
index 4d9e0117..2a64c018 100644
--- a/tests/support/mock_openai_server.rs
+++ b/tests/support/mock_openai_server.rs
@@ -198,15 +198,37 @@ async fn chat_completions_handler(
         .and_then(|r| r.as_str())
         .unwrap_or_default();
 
+    fn extract_text_content(msg: &Value) -> Option<String> {
+        let content = msg.get("content")?;
+        if let Some(s) = content.as_str() {
+            return Some(s.to_string());
+        }
+        if let Some(parts) = content.as_array() {
+            let mut out = String::new();
+            for part in parts {
+                if part.get("type").and_then(|v| v.as_str()) == Some("text")
+                    && let Some(text) = part.get("text").and_then(|v| v.as_str())
+                {
+                    if !out.is_empty() {
+                        out.push(' ');
+                    }
+                    out.push_str(text);
+                }
+            }
+            if !out.is_empty() {
+                return Some(out);
+            }
+        }
+        None
+    }
+
     let latest_user = body
         .pointer("/messages")
         .and_then(|m| m.as_array())
         .and_then(|arr| {
             arr.iter().rev().find_map(|msg| {
                 if msg.get("role").and_then(|r| r.as_str()) == Some("user") {
-                    msg.get("content")
-                        .and_then(|c| c.as_str())
-                        .map(ToOwned::to_owned)
+                    extract_text_content(msg)
                 } else {
                     None
                 }
@@ -215,10 +237,11 @@ async fn chat_completions_handler(
         .unwrap_or_default();
 
     let selected = if last_role == "user" {
+        let latest_user_lower = latest_user.to_ascii_lowercase();
         state
             .rules
             .iter()
-            .find(|r| latest_user.contains(&r.contains))
+            .find(|r| latest_user_lower.contains(&r.contains.to_ascii_lowercase()))
             .map(|r| r.response.clone())
             .unwrap_or_else(|| state.default_response.clone())
     } else {