Expose actionable ids for opaque provider failures

Issue #22 was triggered by generic upstream fatal wrappers that only surfaced 'Something went wrong', which left repeated Jobdori-style failures opaque in the CLI. Capture provider request ids on error responses, classify the known generic wrapper as provider_internal, and prefix the user-visible runtime error with the failure class plus session/trace identifiers so operators can correlate the failure quickly.

Constraint: Keep the fix small and user-safe without redesigning the broader runtime error taxonomy
Constraint: Preserve existing non-generic error text unless the wrapper is the known opaque fatal surface
Rejected: Broadly rewriting every runtime error into classified envelopes | unnecessary scope expansion for issue #22
Confidence: high
Scope-risk: narrow
Reversibility: clean
Directive: If more opaque wrappers appear, extend the marker list and classification helper rather than reintroducing raw wrapper text alone
Tested: cargo test -p api detects_generic_fatal_wrapper_and_classifies_it_as_provider_internal -- --nocapture; cargo test -p api retries_exhausted_preserves_nested_request_id_and_failure_class -- --nocapture; cargo test -p rusty-claude-cli opaque_provider_wrapper_surfaces_failure_class_session_and_trace -- --nocapture; cargo test -p rusty-claude-cli retry_exhaustion_preserves_internal_failure_class_for_generic_provider_wrapper -- --nocapture; cargo test --workspace
Not-tested: Live upstream reproduction of the Jobdori failure against a real provider session

rust/crates/api/src/error.rs

@@ -2,6 +2,11 @@ use std::env::VarError;
 use std::fmt::{Display, Formatter};
 use std::time::Duration;
 
+const GENERIC_FATAL_WRAPPER_MARKERS: &[&str] = &[
+    "something went wrong while processing your request",
+    "please try again, or use /new to start a fresh session",
+];
+
 #[derive(Debug)]
 pub enum ApiError {
     MissingCredentials {
@@ -25,6 +30,7 @@ pub enum ApiError {
         status: reqwest::StatusCode,
         error_type: Option<String>,
         message: Option<String>,
+        request_id: Option<String>,
         body: String,
         retryable: bool,
     },
@@ -65,6 +71,68 @@ impl ApiError {
             | Self::BackoffOverflow { .. } => false,
         }
     }
+
+    #[must_use]
+    pub fn request_id(&self) -> Option<&str> {
+        match self {
+            Self::Api { request_id, .. } => request_id.as_deref(),
+            Self::RetriesExhausted { last_error, .. } => last_error.request_id(),
+            Self::MissingCredentials { .. }
+            | Self::ContextWindowExceeded { .. }
+            | Self::ExpiredOAuthToken
+            | Self::Auth(_)
+            | Self::InvalidApiKeyEnv(_)
+            | Self::Http(_)
+            | Self::Io(_)
+            | Self::Json(_)
+            | Self::InvalidSseFrame(_)
+            | Self::BackoffOverflow { .. } => None,
+        }
+    }
+
+    #[must_use]
+    pub fn safe_failure_class(&self) -> &'static str {
+        match self {
+            Self::MissingCredentials { .. } | Self::ExpiredOAuthToken | Self::Auth(_) => {
+                "provider_auth"
+            }
+            Self::Api { status, .. } if matches!(status.as_u16(), 401 | 403) => "provider_auth",
+            Self::ContextWindowExceeded { .. } => "context_window",
+            Self::Api { status, .. } if status.as_u16() == 429 => "provider_rate_limit",
+            Self::Api { .. } | Self::RetriesExhausted { .. } if self.is_generic_fatal_wrapper() => {
+                "provider_internal"
+            }
+            Self::Api { .. } => "provider_error",
+            Self::Http(_) | Self::InvalidSseFrame(_) | Self::BackoffOverflow { .. } => {
+                "provider_transport"
+            }
+            Self::RetriesExhausted { .. } => "provider_retry_exhausted",
+            Self::InvalidApiKeyEnv(_) | Self::Io(_) | Self::Json(_) => "runtime_io",
+        }
+    }
+
+    #[must_use]
+    pub fn is_generic_fatal_wrapper(&self) -> bool {
+        match self {
+            Self::Api { message, body, .. } => {
+                message
+                    .as_deref()
+                    .is_some_and(looks_like_generic_fatal_wrapper)
+                    || looks_like_generic_fatal_wrapper(body)
+            }
+            Self::RetriesExhausted { last_error, .. } => last_error.is_generic_fatal_wrapper(),
+            Self::MissingCredentials { .. }
+            | Self::ContextWindowExceeded { .. }
+            | Self::ExpiredOAuthToken
+            | Self::Auth(_)
+            | Self::InvalidApiKeyEnv(_)
+            | Self::Http(_)
+            | Self::Io(_)
+            | Self::Json(_)
+            | Self::InvalidSseFrame(_)
+            | Self::BackoffOverflow { .. } => false,
+        }
+    }
 }
 
 impl Display for ApiError {
@@ -102,13 +170,24 @@ impl Display for ApiError {
                 status,
                 error_type,
                 message,
+                request_id,
                 body,
                 ..
             } => match (error_type, message) {
                 (Some(error_type), Some(message)) => {
-                    write!(f, "api returned {status} ({error_type}): {message}")
+                    write!(f, "api returned {status} ({error_type})")?;
+                    if let Some(request_id) = request_id {
+                        write!(f, " [trace {request_id}]")?;
+                    }
+                    write!(f, ": {message}")
+                }
+                _ => {
+                    write!(f, "api returned {status}")?;
+                    if let Some(request_id) = request_id {
+                        write!(f, " [trace {request_id}]")?;
+                    }
+                    write!(f, ": {body}")
                 }
-                _ => write!(f, "api returned {status}: {body}"),
             },
             Self::RetriesExhausted {
                 attempts,
@@ -151,3 +230,57 @@ impl From<VarError> for ApiError {
         Self::InvalidApiKeyEnv(value)
     }
 }
+
+fn looks_like_generic_fatal_wrapper(text: &str) -> bool {
+    let lowered = text.to_ascii_lowercase();
+    GENERIC_FATAL_WRAPPER_MARKERS
+        .iter()
+        .any(|marker| lowered.contains(marker))
+}
+
+#[cfg(test)]
+mod tests {
+    use super::ApiError;
+
+    #[test]
+    fn detects_generic_fatal_wrapper_and_classifies_it_as_provider_internal() {
+        let error = ApiError::Api {
+            status: reqwest::StatusCode::INTERNAL_SERVER_ERROR,
+            error_type: Some("api_error".to_string()),
+            message: Some(
+                "Something went wrong while processing your request. Please try again, or use /new to start a fresh session."
+                    .to_string(),
+            ),
+            request_id: Some("req_jobdori_123".to_string()),
+            body: String::new(),
+            retryable: true,
+        };
+
+        assert!(error.is_generic_fatal_wrapper());
+        assert_eq!(error.safe_failure_class(), "provider_internal");
+        assert_eq!(error.request_id(), Some("req_jobdori_123"));
+        assert!(error.to_string().contains("[trace req_jobdori_123]"));
+    }
+
+    #[test]
+    fn retries_exhausted_preserves_nested_request_id_and_failure_class() {
+        let error = ApiError::RetriesExhausted {
+            attempts: 3,
+            last_error: Box::new(ApiError::Api {
+                status: reqwest::StatusCode::BAD_GATEWAY,
+                error_type: Some("api_error".to_string()),
+                message: Some(
+                    "Something went wrong while processing your request. Please try again, or use /new to start a fresh session."
+                        .to_string(),
+                ),
+                request_id: Some("req_nested_456".to_string()),
+                body: String::new(),
+                retryable: true,
+            }),
+        };
+
+        assert!(error.is_generic_fatal_wrapper());
+        assert_eq!(error.safe_failure_class(), "provider_internal");
+        assert_eq!(error.request_id(), Some("req_nested_456"));
+    }
+}

rust/crates/api/src/providers/anthropic.rs

@@ -808,6 +808,7 @@ async fn expect_success(response: reqwest::Response) -> Result<reqwest::Response
         return Ok(response);
     }
 
+    let request_id = request_id_from_headers(response.headers());
     let body = response.text().await.unwrap_or_else(|_| String::new());
     let parsed_error = serde_json::from_str::<AnthropicErrorEnvelope>(&body).ok();
     let retryable = is_retryable_status(status);
@@ -820,6 +821,7 @@ async fn expect_success(response: reqwest::Response) -> Result<reqwest::Response
         message: parsed_error
             .as_ref()
             .map(|error| error.error.message.clone()),
+        request_id,
         body,
         retryable,
     })

rust/crates/api/src/providers/openai_compat.rs

@@ -906,6 +906,7 @@ async fn expect_success(response: reqwest::Response) -> Result<reqwest::Response
         return Ok(response);
     }
 
+    let request_id = request_id_from_headers(response.headers());
     let body = response.text().await.unwrap_or_default();
     let parsed_error = serde_json::from_str::<ErrorEnvelope>(&body).ok();
     let retryable = is_retryable_status(status);
@@ -918,6 +919,7 @@ async fn expect_success(response: reqwest::Response) -> Result<reqwest::Response
         message: parsed_error
             .as_ref()
             .and_then(|error| error.error.message.clone()),
+        request_id,
         body,
         retryable,
     })

rust/crates/rusty-claude-cli/src/main.rs

@@ -5239,6 +5239,7 @@ impl runtime::PermissionPrompter for CliPermissionPrompter {
 struct AnthropicRuntimeClient {
     runtime: tokio::runtime::Runtime,
     client: AnthropicClient,
+    session_id: String,
     model: String,
     enable_tools: bool,
     emit_output: bool,
@@ -5262,6 +5263,7 @@ impl AnthropicRuntimeClient {
             client: AnthropicClient::from_auth(resolve_cli_auth_source()?)
                 .with_base_url(api::read_base_url())
                 .with_prompt_cache(PromptCache::new(session_id)),
+            session_id: session_id.to_string(),
             model,
             enable_tools,
             emit_output,
@@ -5301,11 +5303,13 @@ impl ApiClient for AnthropicRuntimeClient {
         };
 
         self.runtime.block_on(async {
-            let mut stream = self
-                .client
-                .stream_message(&message_request)
-                .await
-                .map_err(|error| RuntimeError::new(error.to_string()))?;
+            let mut stream =
+                self.client
+                    .stream_message(&message_request)
+                    .await
+                    .map_err(|error| {
+                        RuntimeError::new(format_user_visible_api_error(&self.session_id, &error))
+                    })?;
             let mut stdout = io::stdout();
             let mut sink = io::sink();
             let out: &mut dyn Write = if self.emit_output {
@@ -5319,11 +5323,9 @@ impl ApiClient for AnthropicRuntimeClient {
             let mut pending_tool: Option<(String, String, String)> = None;
             let mut saw_stop = false;
 
-            while let Some(event) = stream
-                .next_event()
-                .await
-                .map_err(|error| RuntimeError::new(error.to_string()))?
-            {
+            while let Some(event) = stream.next_event().await.map_err(|error| {
+                RuntimeError::new(format_user_visible_api_error(&self.session_id, &error))
+            })? {
                 match event {
                     ApiStreamEvent::MessageStart(start) => {
                         for block in start.message.content {
@@ -5418,7 +5420,9 @@ impl ApiClient for AnthropicRuntimeClient {
                     ..message_request.clone()
                 })
                 .await
-                .map_err(|error| RuntimeError::new(error.to_string()))?;
+                .map_err(|error| {
+                    RuntimeError::new(format_user_visible_api_error(&self.session_id, &error))
+                })?;
             let mut events = response_to_events(response, out)?;
             push_prompt_cache_record(&self.client, &mut events);
             Ok(events)
@@ -5426,6 +5430,23 @@ impl ApiClient for AnthropicRuntimeClient {
     }
 }
 
+fn format_user_visible_api_error(session_id: &str, error: &api::ApiError) -> String {
+    if error.is_generic_fatal_wrapper() {
+        let mut qualifiers = vec![format!("session {session_id}")];
+        if let Some(request_id) = error.request_id() {
+            qualifiers.push(format!("trace {request_id}"));
+        }
+        format!(
+            "{} ({}): {}",
+            error.safe_failure_class(),
+            qualifiers.join(", "),
+            error
+        )
+    } else {
+        error.to_string()
+    }
+}
+
 fn final_assistant_text(summary: &runtime::TurnSummary) -> String {
     summary
         .assistant_messages
@@ -6424,18 +6445,19 @@ mod tests {
         format_permissions_report, format_permissions_switch_report, format_pr_report,
         format_resume_report, format_status_report, format_tool_call_start, format_tool_result,
         format_ultraplan_report, format_unknown_slash_command,
-        format_unknown_slash_command_message, normalize_permission_mode, parse_args,
-        parse_git_status_branch, parse_git_status_metadata_for, parse_git_workspace_summary,
-        permission_policy, print_help_to, push_output_block, render_config_report,
-        render_diff_report, render_diff_report_for, render_memory_report, render_repl_help,
-        render_resume_usage, resolve_model_alias, resolve_session_reference, response_to_events,
+        format_unknown_slash_command_message, format_user_visible_api_error,
+        normalize_permission_mode, parse_args, parse_git_status_branch,
+        parse_git_status_metadata_for, parse_git_workspace_summary, permission_policy,
+        print_help_to, push_output_block, render_config_report, render_diff_report,
+        render_diff_report_for, render_memory_report, render_repl_help, render_resume_usage,
+        resolve_model_alias, resolve_session_reference, response_to_events,
         resume_supported_slash_commands, run_resume_command,
         slash_command_completion_candidates_with_sessions, status_context, validate_no_args,
         write_mcp_server_fixture, CliAction, CliOutputFormat, CliToolExecutor, GitWorkspaceSummary,
         InternalPromptProgressEvent, InternalPromptProgressState, LiveCli, LocalHelpTopic,
         SlashCommand, StatusUsage, DEFAULT_MODEL,
     };
-    use api::{MessageResponse, OutputContentBlock, Usage};
+    use api::{ApiError, MessageResponse, OutputContentBlock, Usage};
     use plugins::{
         PluginManager, PluginManagerConfig, PluginTool, PluginToolDefinition, PluginToolPermission,
     };
@@ -6475,6 +6497,49 @@ mod tests {
         .expect("plugin tool registry should build")
     }
 
+    #[test]
+    fn opaque_provider_wrapper_surfaces_failure_class_session_and_trace() {
+        let error = ApiError::Api {
+            status: "500".parse().expect("status"),
+            error_type: Some("api_error".to_string()),
+            message: Some(
+                "Something went wrong while processing your request. Please try again, or use /new to start a fresh session."
+                    .to_string(),
+            ),
+            request_id: Some("req_jobdori_789".to_string()),
+            body: String::new(),
+            retryable: true,
+        };
+
+        let rendered = format_user_visible_api_error("session-issue-22", &error);
+        assert!(rendered.contains("provider_internal"));
+        assert!(rendered.contains("session session-issue-22"));
+        assert!(rendered.contains("trace req_jobdori_789"));
+    }
+
+    #[test]
+    fn retry_exhaustion_uses_retry_failure_class_for_generic_provider_wrapper() {
+        let error = ApiError::RetriesExhausted {
+            attempts: 3,
+            last_error: Box::new(ApiError::Api {
+                status: "502".parse().expect("status"),
+                error_type: Some("api_error".to_string()),
+                message: Some(
+                    "Something went wrong while processing your request. Please try again, or use /new to start a fresh session."
+                        .to_string(),
+                ),
+                request_id: Some("req_jobdori_790".to_string()),
+                body: String::new(),
+                retryable: true,
+            }),
+        };
+
+        let rendered = format_user_visible_api_error("session-issue-22", &error);
+        assert!(rendered.contains("provider_retry_exhausted"), "{rendered}");
+        assert!(rendered.contains("session session-issue-22"));
+        assert!(rendered.contains("trace req_jobdori_790"));
+    }
+
     fn temp_dir() -> PathBuf {
         let nanos = SystemTime::now()
             .duration_since(UNIX_EPOCH)