From 6ac13ffdad25872a963a688fd26dffe75d01074d Mon Sep 17 00:00:00 2001
From: Andreas Haida <andreas.haida@gmail.com>
Date: Sun, 3 May 2026 18:44:03 +0200
Subject: [PATCH] Handle OpenAI token-limit errors as context-window failures

---
 rust/crates/api/src/error.rs             | 25 ++++++++++++++++++
 rust/crates/rusty-claude-cli/src/main.rs | 33 ++++++++++++++++++++++++
 2 files changed, 58 insertions(+)

diff --git a/rust/crates/api/src/error.rs b/rust/crates/api/src/error.rs
index 836f46e0..21d980af 100644
--- a/rust/crates/api/src/error.rs
+++ b/rust/crates/api/src/error.rs
@@ -14,6 +14,11 @@ const CONTEXT_WINDOW_ERROR_MARKERS: &[&str] = &[
     "too many tokens",
     "prompt is too long",
     "input is too long",
+    "input tokens exceed",
+    "configured limit",
+    "messages resulted in",
+    "completion tokens",
+    "prompt tokens",
     "request is too large",
 ];
 
@@ -542,6 +547,26 @@ mod tests {
         assert_eq!(error.request_id(), Some("req_ctx_123"));
     }
 
+    #[test]
+    fn classifies_openai_configured_limit_errors_as_context_window_failures() {
+        let error = ApiError::Api {
+            status: reqwest::StatusCode::BAD_REQUEST,
+            error_type: Some("invalid_request_error".to_string()),
+            message: Some(
+                "Input tokens exceed the configured limit of 922000 tokens. Your messages resulted in 1860900 tokens. Please reduce the length of the messages."
+                    .to_string(),
+            ),
+            request_id: Some("req_ctx_openai_123".to_string()),
+            body: String::new(),
+            retryable: false,
+            suggested_action: None,
+        };
+
+        assert!(error.is_context_window_failure());
+        assert_eq!(error.safe_failure_class(), "context_window");
+        assert_eq!(error.request_id(), Some("req_ctx_openai_123"));
+    }
+
     #[test]
     fn missing_credentials_without_hint_renders_the_canonical_message() {
         // given
diff --git a/rust/crates/rusty-claude-cli/src/main.rs b/rust/crates/rusty-claude-cli/src/main.rs
index dbdbd07b..e2c889e9 100644
--- a/rust/crates/rusty-claude-cli/src/main.rs
+++ b/rust/crates/rusty-claude-cli/src/main.rs
@@ -9424,6 +9424,39 @@ mod tests {
         );
     }
 
+    #[test]
+    fn openai_configured_limit_errors_are_rendered_as_context_window_guidance() {
+        let error = ApiError::Api {
+            status: "400".parse().expect("status"),
+            error_type: Some("invalid_request_error".to_string()),
+            message: Some(
+                "Input tokens exceed the configured limit of 922000 tokens. Your messages resulted in 1860900 tokens. Please reduce the length of the messages."
+                    .to_string(),
+            ),
+            request_id: Some("req_ctx_openai_456".to_string()),
+            body: String::new(),
+            retryable: false,
+            suggested_action: None,
+        };
+
+        let rendered = format_user_visible_api_error("session-issue-32", &error);
+        assert!(rendered.contains("Context window blocked"), "{rendered}");
+        assert!(rendered.contains("context_window_blocked"), "{rendered}");
+        assert!(
+            rendered.contains("Trace            req_ctx_openai_456"),
+            "{rendered}"
+        );
+        assert!(
+            rendered.contains("Detail           Input tokens exceed the configured limit of 922000 tokens."),
+            "{rendered}"
+        );
+        assert!(rendered.contains("Compact          /compact"), "{rendered}");
+        assert!(
+            rendered.contains("Fresh session    /clear --confirm"),
+            "{rendered}"
+        );
+    }
+
     #[test]
     fn retry_wrapped_context_window_errors_keep_recovery_guidance() {
         let error = ApiError::RetriesExhausted {