diff --git a/codex-rs/core/tests/suite/resume.rs b/codex-rs/core/tests/suite/resume.rs
index 98a570a1d..b5889c9aa 100644
--- a/codex-rs/core/tests/suite/resume.rs
+++ b/codex-rs/core/tests/suite/resume.rs
@@ -13,10 +13,49 @@ use core_test_support::responses::mount_sse_sequence;
 use core_test_support::responses::sse;
 use core_test_support::responses::start_mock_server;
 use core_test_support::skip_if_no_network;
+use core_test_support::test_codex::TestCodex;
+use core_test_support::test_codex::TestCodexBuilder;
 use core_test_support::test_codex::test_codex;
 use core_test_support::wait_for_event;
 use pretty_assertions::assert_eq;
+use std::path::PathBuf;
 use std::sync::Arc;
+use std::time::Duration;
+use tempfile::TempDir;
+use wiremock::MockServer;
+
+async fn resume_until_initial_messages(
+    builder: &mut TestCodexBuilder,
+    server: &MockServer,
+    home: Arc<TempDir>,
+    rollout_path: PathBuf,
+    predicate: impl Fn(&[EventMsg]) -> bool,
+) -> Result<TestCodex> {
+    let deadline = tokio::time::Instant::now() + Duration::from_secs(2);
+    let poll_interval = Duration::from_millis(10);
+    let mut last_initial_messages = "<missing initial messages>".to_string();
+
+    loop {
+        let resumed = builder
+            .resume(server, Arc::clone(&home), rollout_path.clone())
+            .await?;
+        if let Some(initial_messages) = resumed.session_configured.initial_messages.as_ref() {
+            if predicate(initial_messages) {
+                return Ok(resumed);
+            }
+            last_initial_messages = format!("{initial_messages:#?}");
+        }
+
+        if tokio::time::Instant::now() >= deadline {
+            panic!(
+                "timed out waiting for rollout resume messages to stabilize: {last_initial_messages}"
+            );
+        }
+
+        drop(resumed);
+        tokio::time::sleep(poll_interval).await;
+    }
+}
 
 #[tokio::test(flavor = "multi_thread", worker_threads = 2)]
 async fn resume_includes_initial_messages_from_rollout_events() -> Result<()> {
@@ -57,7 +96,26 @@ async fn resume_includes_initial_messages_from_rollout_events() -> Result<()> {
 
     wait_for_event(&codex, |event| matches!(event, EventMsg::TurnComplete(_))).await;
 
-    let resumed = builder.resume(&server, home, rollout_path).await?;
+    let resumed = resume_until_initial_messages(
+        &mut builder,
+        &server,
+        home,
+        rollout_path,
+        |initial_messages| {
+            matches!(
+                initial_messages,
+                [
+                    EventMsg::TurnStarted(_),
+                    EventMsg::UserMessage(_),
+                    EventMsg::TokenCount(_),
+                    EventMsg::AgentMessage(_),
+                    EventMsg::TokenCount(_),
+                    EventMsg::TurnComplete(_),
+                ]
+            )
+        },
+    )
+    .await?;
     let initial_messages = resumed
         .session_configured
         .initial_messages
@@ -123,7 +181,28 @@ async fn resume_includes_initial_messages_from_reasoning_events() -> Result<()>
 
     wait_for_event(&codex, |event| matches!(event, EventMsg::TurnComplete(_))).await;
 
-    let resumed = builder.resume(&server, home, rollout_path).await?;
+    let resumed = resume_until_initial_messages(
+        &mut builder,
+        &server,
+        home,
+        rollout_path,
+        |initial_messages| {
+            matches!(
+                initial_messages,
+                [
+                    EventMsg::TurnStarted(_),
+                    EventMsg::UserMessage(_),
+                    EventMsg::TokenCount(_),
+                    EventMsg::AgentReasoning(_),
+                    EventMsg::AgentReasoningRawContent(_),
+                    EventMsg::AgentMessage(_),
+                    EventMsg::TokenCount(_),
+                    EventMsg::TurnComplete(_),
+                ]
+            )
+        },
+    )
+    .await?;
     let initial_messages = resumed
         .session_configured
         .initial_messages