diff --git a/codex-rs/utils/readiness/src/lib.rs b/codex-rs/utils/readiness/src/lib.rs
index 8b92f9387a1..ff99c3df8e9 100644
--- a/codex-rs/utils/readiness/src/lib.rs
+++ b/codex-rs/utils/readiness/src/lib.rs
@@ -118,26 +118,25 @@ impl Readiness for ReadinessFlag {
             return Err(errors::ReadinessError::FlagAlreadyReady);
         }
 
-        // Generate a token; ensure it's not 0.
-        let token = Token(self.next_id.fetch_add(1, Ordering::Relaxed));
-
         // Recheck readiness while holding the lock so mark_ready can't flip the flag between the
-        // check above and inserting the token.
-        let inserted = self
+        // check above and inserting the token. Also ensure the token is non-zero and unique in
+        // the presence of `i32` wrap-around.
+        let token = self
             .with_tokens(|tokens| {
                 if self.load_ready() {
-                    return false;
+                    return None;
+                }
+
+                loop {
+                    let token = Token(self.next_id.fetch_add(1, Ordering::Relaxed));
+                    if token.0 != 0 && tokens.insert(token) {
+                        return Some(token);
+                    }
                 }
-                tokens.insert(token);
-                true
             })
             .await?;
 
-        if !inserted {
-            return Err(errors::ReadinessError::FlagAlreadyReady);
-        }
-
-        Ok(token)
+        token.ok_or(errors::ReadinessError::FlagAlreadyReady)
     }
 
     async fn mark_ready(&self, token: Token) -> Result<bool, errors::ReadinessError> {
@@ -199,6 +198,7 @@ mod errors {
 #[cfg(test)]
 mod tests {
     use std::sync::Arc;
+    use std::sync::atomic::Ordering;
 
     use super::Readiness;
     use super::ReadinessFlag;
@@ -289,4 +289,26 @@ mod tests {
             .expect_err("contended subscribe should report a lock failure");
         assert_matches!(err, ReadinessError::TokenLockFailed);
     }
+
+    #[tokio::test]
+    async fn subscribe_skips_zero_token() -> Result<(), ReadinessError> {
+        let flag = ReadinessFlag::new();
+        flag.next_id.store(0, Ordering::Relaxed);
+
+        let token = flag.subscribe().await?;
+        assert_ne!(token, Token(0));
+        assert!(flag.mark_ready(token).await?);
+        Ok(())
+    }
+
+    #[tokio::test]
+    async fn subscribe_avoids_duplicate_tokens() -> Result<(), ReadinessError> {
+        let flag = ReadinessFlag::new();
+        let token = flag.subscribe().await?;
+        flag.next_id.store(token.0, Ordering::Relaxed);
+
+        let token2 = flag.subscribe().await?;
+        assert_ne!(token2, token);
+        Ok(())
+    }
 }