Enforce machine-readable output across CLI surfaces

Promote doctor into a real top-level CLI action, reuse the same local report for resumed and REPL doctor invocations, and intercept doctor/status/sandbox help flags before prompt-mode dispatch. The parser change also closes the help fallthrough that previously wandered into runtime startup for local-info commands.

Constraint: Preserve prompt shorthand for normal multi-word text input while fixing exact local subcommand help paths
Rejected: Route \7⠋ 🦀 Thinking...8✘ ❌ Request failed
 through prompt/slash guidance | still shells out through the wrong surface and keeps health checks hidden
Rejected: Reuse the status report as doctor output | status does not explain auth/config health or expose a dedicated diagnostic summary
Confidence: high
Scope-risk: narrow
Directive: Keep doctor local-only unless an explicit network probe is intentionally added and separately tested
Tested: cargo build -p rusty-claude-cli; cargo test -p rusty-claude-cli; cargo run -p rusty-claude-cli -- doctor --help; CLAW_CONFIG_HOME=/tmp/tmp.7pm9SVzOPN ANTHROPIC_API_KEY= ANTHROPIC_AUTH_TOKEN= cargo run -p rusty-claude-cli -- doctor
Not-tested: direct /doctor outside the REPL remains interactive-only

rust/.claw/sessions/session-1775386832313-0.jsonl

@@ -0,0 +1,2 @@
+{"created_at_ms":1775386832313,"session_id":"session-1775386832313-0","type":"session_meta","updated_at_ms":1775386832313,"version":1}
+{"message":{"blocks":[{"text":"status --help","type":"text"}],"role":"user"},"type":"message"}

rust/.claw/sessions/session-1775386842352-0.jsonl

@@ -0,0 +1,2 @@
+{"created_at_ms":1775386842352,"session_id":"session-1775386842352-0","type":"session_meta","updated_at_ms":1775386842352,"version":1}
+{"message":{"blocks":[{"text":"doctor --help","type":"text"}],"role":"user"},"type":"message"}

rust/.claw/sessions/session-1775386852257-0.jsonl

@@ -0,0 +1,2 @@
+{"created_at_ms":1775386852257,"session_id":"session-1775386852257-0","type":"session_meta","updated_at_ms":1775386852257,"version":1}
+{"message":{"blocks":[{"text":"doctor --help","type":"text"}],"role":"user"},"type":"message"}

rust/.claw/sessions/session-1775386853666-0.jsonl

@@ -0,0 +1,2 @@
+{"created_at_ms":1775386853666,"session_id":"session-1775386853666-0","type":"session_meta","updated_at_ms":1775386853666,"version":1}
+{"message":{"blocks":[{"text":"status --help","type":"text"}],"role":"user"},"type":"message"}

rust/crates/api/src/error.rs

@@ -8,6 +8,13 @@ pub enum ApiError {
         provider: &'static str,
         env_vars: &'static [&'static str],
     },
+    ContextWindowExceeded {
+        model: String,
+        estimated_input_tokens: u32,
+        requested_output_tokens: u32,
+        estimated_total_tokens: u32,
+        context_window_tokens: u32,
+    },
     ExpiredOAuthToken,
     Auth(String),
     InvalidApiKeyEnv(VarError),
@@ -48,6 +55,7 @@ impl ApiError {
             Self::Api { retryable, .. } => *retryable,
             Self::RetriesExhausted { last_error, .. } => last_error.is_retryable(),
             Self::MissingCredentials { .. }
+            | Self::ContextWindowExceeded { .. }
             | Self::ExpiredOAuthToken
             | Self::Auth(_)
             | Self::InvalidApiKeyEnv(_)
@@ -67,6 +75,16 @@ impl Display for ApiError {
                 "missing {provider} credentials; export {} before calling the {provider} API",
                 env_vars.join(" or ")
             ),
+            Self::ContextWindowExceeded {
+                model,
+                estimated_input_tokens,
+                requested_output_tokens,
+                estimated_total_tokens,
+                context_window_tokens,
+            } => write!(
+                f,
+                "context_window_blocked for {model}: estimated input {estimated_input_tokens} + requested output {requested_output_tokens} = {estimated_total_tokens} tokens exceeds the {context_window_tokens}-token context window; compact the session or reduce request size before retrying"
+            ),
             Self::ExpiredOAuthToken => {
                 write!(
                     f,

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

@@ -14,7 +14,7 @@ use telemetry::{AnalyticsEvent, AnthropicRequestProfile, ClientIdentity, Session
 use crate::error::ApiError;
 use crate::prompt_cache::{PromptCache, PromptCacheRecord, PromptCacheStats};
 
-use super::{Provider, ProviderFuture};
+use super::{preflight_message_request, Provider, ProviderFuture};
 use crate::sse::SseParser;
 use crate::types::{MessageDeltaEvent, MessageRequest, MessageResponse, StreamEvent, Usage};
 
@@ -294,6 +294,8 @@ impl AnthropicClient {
             }
         }
 
+        preflight_message_request(&request)?;
+
         let response = self.send_with_retry(&request).await?;
         let request_id = request_id_from_headers(response.headers());
         let mut response = response
@@ -337,6 +339,7 @@ impl AnthropicClient {
         &self,
         request: &MessageRequest,
     ) -> Result<MessageStream, ApiError> {
+        preflight_message_request(request)?;
         let response = self
             .send_with_retry(&request.clone().with_streaming())
             .await?;

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

@@ -1,6 +1,8 @@
 use std::future::Future;
 use std::pin::Pin;
 
+use serde::Serialize;
+
 use crate::error::ApiError;
 use crate::types::{MessageRequest, MessageResponse};
 
@@ -40,6 +42,12 @@ pub struct ProviderMetadata {
     pub default_base_url: &'static str,
 }
 
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub struct ModelTokenLimit {
+    pub max_output_tokens: u32,
+    pub context_window_tokens: u32,
+}
+
 const MODEL_REGISTRY: &[(&str, ProviderMetadata)] = &[
     (
         "opus",
@@ -182,17 +190,86 @@ pub fn detect_provider_kind(model: &str) -> ProviderKind {
 
 #[must_use]
 pub fn max_tokens_for_model(model: &str) -> u32 {
+    model_token_limit(model).map_or_else(
+        || {
+            let canonical = resolve_model_alias(model);
+            if canonical.contains("opus") {
+                32_000
+            } else {
+                64_000
+            }
+        },
+        |limit| limit.max_output_tokens,
+    )
+}
+
+#[must_use]
+pub fn model_token_limit(model: &str) -> Option<ModelTokenLimit> {
     let canonical = resolve_model_alias(model);
-    if canonical.contains("opus") {
-        32_000
-    } else {
-        64_000
+    match canonical.as_str() {
+        "claude-opus-4-6" => Some(ModelTokenLimit {
+            max_output_tokens: 32_000,
+            context_window_tokens: 200_000,
+        }),
+        "claude-sonnet-4-6" | "claude-haiku-4-5-20251213" => Some(ModelTokenLimit {
+            max_output_tokens: 64_000,
+            context_window_tokens: 200_000,
+        }),
+        "grok-3" | "grok-3-mini" => Some(ModelTokenLimit {
+            max_output_tokens: 64_000,
+            context_window_tokens: 131_072,
+        }),
+        _ => None,
     }
 }
 
+pub fn preflight_message_request(request: &MessageRequest) -> Result<(), ApiError> {
+    let Some(limit) = model_token_limit(&request.model) else {
+        return Ok(());
+    };
+
+    let estimated_input_tokens = estimate_message_request_input_tokens(request);
+    let estimated_total_tokens = estimated_input_tokens.saturating_add(request.max_tokens);
+    if estimated_total_tokens > limit.context_window_tokens {
+        return Err(ApiError::ContextWindowExceeded {
+            model: resolve_model_alias(&request.model),
+            estimated_input_tokens,
+            requested_output_tokens: request.max_tokens,
+            estimated_total_tokens,
+            context_window_tokens: limit.context_window_tokens,
+        });
+    }
+
+    Ok(())
+}
+
+fn estimate_message_request_input_tokens(request: &MessageRequest) -> u32 {
+    let mut estimate = estimate_serialized_tokens(&request.messages);
+    estimate = estimate.saturating_add(estimate_serialized_tokens(&request.system));
+    estimate = estimate.saturating_add(estimate_serialized_tokens(&request.tools));
+    estimate = estimate.saturating_add(estimate_serialized_tokens(&request.tool_choice));
+    estimate
+}
+
+fn estimate_serialized_tokens<T: Serialize>(value: &T) -> u32 {
+    serde_json::to_vec(value)
+        .ok()
+        .map_or(0, |bytes| (bytes.len() / 4 + 1) as u32)
+}
+
 #[cfg(test)]
 mod tests {
-    use super::{detect_provider_kind, max_tokens_for_model, resolve_model_alias, ProviderKind};
+    use serde_json::json;
+
+    use crate::error::ApiError;
+    use crate::types::{
+        InputContentBlock, InputMessage, MessageRequest, ToolChoice, ToolDefinition,
+    };
+
+    use super::{
+        detect_provider_kind, max_tokens_for_model, model_token_limit, preflight_message_request,
+        resolve_model_alias, ProviderKind,
+    };
 
     #[test]
     fn resolves_grok_aliases() {
@@ -215,4 +292,86 @@ mod tests {
         assert_eq!(max_tokens_for_model("opus"), 32_000);
         assert_eq!(max_tokens_for_model("grok-3"), 64_000);
     }
+
+    #[test]
+    fn returns_context_window_metadata_for_supported_models() {
+        assert_eq!(
+            model_token_limit("claude-sonnet-4-6")
+                .expect("claude-sonnet-4-6 should be registered")
+                .context_window_tokens,
+            200_000
+        );
+        assert_eq!(
+            model_token_limit("grok-mini")
+                .expect("grok-mini should resolve to a registered model")
+                .context_window_tokens,
+            131_072
+        );
+    }
+
+    #[test]
+    fn preflight_blocks_requests_that_exceed_the_model_context_window() {
+        let request = MessageRequest {
+            model: "claude-sonnet-4-6".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(600_000),
+                }],
+            }],
+            system: Some("Keep the answer short.".to_string()),
+            tools: Some(vec![ToolDefinition {
+                name: "weather".to_string(),
+                description: Some("Fetches weather".to_string()),
+                input_schema: json!({
+                    "type": "object",
+                    "properties": { "city": { "type": "string" } },
+                }),
+            }]),
+            tool_choice: Some(ToolChoice::Auto),
+            stream: true,
+        };
+
+        let error = preflight_message_request(&request)
+            .expect_err("oversized request should be rejected before the provider call");
+
+        match error {
+            ApiError::ContextWindowExceeded {
+                model,
+                estimated_input_tokens,
+                requested_output_tokens,
+                estimated_total_tokens,
+                context_window_tokens,
+            } => {
+                assert_eq!(model, "claude-sonnet-4-6");
+                assert!(estimated_input_tokens > 136_000);
+                assert_eq!(requested_output_tokens, 64_000);
+                assert!(estimated_total_tokens > context_window_tokens);
+                assert_eq!(context_window_tokens, 200_000);
+            }
+            other => panic!("expected context-window preflight failure, got {other:?}"),
+        }
+    }
+
+    #[test]
+    fn preflight_skips_unknown_models() {
+        let request = MessageRequest {
+            model: "unknown-model".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(600_000),
+                }],
+            }],
+            system: None,
+            tools: None,
+            tool_choice: None,
+            stream: false,
+        };
+
+        preflight_message_request(&request)
+            .expect("models without context metadata should skip the guarded preflight");
+    }
 }

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

@@ -12,7 +12,7 @@ use crate::types::{
     ToolChoice, ToolDefinition, ToolResultContentBlock, Usage,
 };
 
-use super::{Provider, ProviderFuture};
+use super::{preflight_message_request, Provider, ProviderFuture};
 
 pub const DEFAULT_XAI_BASE_URL: &str = "https://api.x.ai/v1";
 pub const DEFAULT_OPENAI_BASE_URL: &str = "https://api.openai.com/v1";
@@ -128,6 +128,7 @@ impl OpenAiCompatClient {
             stream: false,
             ..request.clone()
         };
+        preflight_message_request(&request)?;
         let response = self.send_with_retry(&request).await?;
         let request_id = request_id_from_headers(response.headers());
         let payload = response.json::<ChatCompletionResponse>().await?;
@@ -142,6 +143,7 @@ impl OpenAiCompatClient {
         &self,
         request: &MessageRequest,
     ) -> Result<MessageStream, ApiError> {
+        preflight_message_request(request)?;
         let response = self
             .send_with_retry(&request.clone().with_streaming())
             .await?;

rust/crates/api/tests/client_integration.rs

@@ -103,6 +103,41 @@ async fn send_message_posts_json_and_parses_response() {
     );
 }
 
+#[tokio::test]
+async fn send_message_blocks_oversized_requests_before_the_http_call() {
+    let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));
+    let server = spawn_server(
+        state.clone(),
+        vec![http_response("200 OK", "application/json", "{}")],
+    )
+    .await;
+
+    let client = AnthropicClient::new("test-key").with_base_url(server.base_url());
+    let error = client
+        .send_message(&MessageRequest {
+            model: "claude-sonnet-4-6".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(600_000),
+                }],
+            }],
+            system: Some("Keep the answer short.".to_string()),
+            tools: None,
+            tool_choice: None,
+            stream: false,
+        })
+        .await
+        .expect_err("oversized request should fail local context-window preflight");
+
+    assert!(matches!(error, ApiError::ContextWindowExceeded { .. }));
+    assert!(
+        state.lock().await.is_empty(),
+        "preflight failure should avoid any upstream HTTP request"
+    );
+}
+
 #[tokio::test]
 async fn send_message_applies_request_profile_and_records_telemetry() {
     let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));

rust/crates/api/tests/openai_compat_integration.rs

@@ -4,10 +4,10 @@ use std::sync::Arc;
 use std::sync::{Mutex as StdMutex, OnceLock};
 
 use api::{
-    ContentBlockDelta, ContentBlockDeltaEvent, ContentBlockStartEvent, ContentBlockStopEvent,
-    InputContentBlock, InputMessage, MessageDeltaEvent, MessageRequest, OpenAiCompatClient,
-    OpenAiCompatConfig, OutputContentBlock, ProviderClient, StreamEvent, ToolChoice,
-    ToolDefinition,
+    ApiError, ContentBlockDelta, ContentBlockDeltaEvent, ContentBlockStartEvent,
+    ContentBlockStopEvent, InputContentBlock, InputMessage, MessageDeltaEvent, MessageRequest,
+    OpenAiCompatClient, OpenAiCompatConfig, OutputContentBlock, ProviderClient, StreamEvent,
+    ToolChoice, ToolDefinition,
 };
 use serde_json::json;
 use tokio::io::{AsyncReadExt, AsyncWriteExt};
@@ -63,6 +63,42 @@ async fn send_message_uses_openai_compatible_endpoint_and_auth() {
     assert_eq!(body["tools"][0]["type"], json!("function"));
 }
 
+#[tokio::test]
+async fn send_message_blocks_oversized_xai_requests_before_the_http_call() {
+    let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));
+    let server = spawn_server(
+        state.clone(),
+        vec![http_response("200 OK", "application/json", "{}")],
+    )
+    .await;
+
+    let client = OpenAiCompatClient::new("xai-test-key", OpenAiCompatConfig::xai())
+        .with_base_url(server.base_url());
+    let error = client
+        .send_message(&MessageRequest {
+            model: "grok-3".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(300_000),
+                }],
+            }],
+            system: Some("Keep the answer short.".to_string()),
+            tools: None,
+            tool_choice: None,
+            stream: false,
+        })
+        .await
+        .expect_err("oversized request should fail local context-window preflight");
+
+    assert!(matches!(error, ApiError::ContextWindowExceeded { .. }));
+    assert!(
+        state.lock().await.is_empty(),
+        "preflight failure should avoid any upstream HTTP request"
+    );
+}
+
 #[tokio::test]
 async fn send_message_accepts_full_chat_completions_endpoint_override() {
     let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));

rust/crates/runtime/src/lane_events.rs

@@ -114,8 +114,12 @@ impl LaneEvent {
 
     #[must_use]
     pub fn finished(emitted_at: impl Into<String>, detail: Option<String>) -> Self {
-        Self::new(LaneEventName::Finished, LaneEventStatus::Completed, emitted_at)
-            .with_optional_detail(detail)
+        Self::new(
+            LaneEventName::Finished,
+            LaneEventStatus::Completed,
+            emitted_at,
+        )
+        .with_optional_detail(detail)
     }
 
     #[must_use]
@@ -161,19 +165,14 @@ impl LaneEvent {
 mod tests {
     use serde_json::json;
 
-    use super::{
-        LaneEvent, LaneEventBlocker, LaneEventName, LaneEventStatus, LaneFailureClass,
-    };
+    use super::{LaneEvent, LaneEventBlocker, LaneEventName, LaneEventStatus, LaneFailureClass};
 
     #[test]
     fn canonical_lane_event_names_serialize_to_expected_wire_values() {
         let cases = [
             (LaneEventName::Started, "lane.started"),
             (LaneEventName::Ready, "lane.ready"),
-            (
-                LaneEventName::PromptMisdelivery,
-                "lane.prompt_misdelivery",
-            ),
+            (LaneEventName::PromptMisdelivery, "lane.prompt_misdelivery"),
             (LaneEventName::Blocked, "lane.blocked"),
             (LaneEventName::Red, "lane.red"),
             (LaneEventName::Green, "lane.green"),
@@ -193,7 +192,10 @@ mod tests {
         ];
 
         for (event, expected) in cases {
-            assert_eq!(serde_json::to_value(event).expect("serialize event"), json!(expected));
+            assert_eq!(
+                serde_json::to_value(event).expect("serialize event"),
+                json!(expected)
+            );
         }
     }
 

rust/crates/runtime/src/mcp_lifecycle_hardened.rs

@@ -599,7 +599,10 @@ mod tests {
             ));
 
             match result {
-                McpPhaseResult::Failure { phase: failed_phase, error } => {
+                McpPhaseResult::Failure {
+                    phase: failed_phase,
+                    error,
+                } => {
                     assert_eq!(failed_phase, phase);
                     assert_eq!(error.phase, phase);
                     assert_eq!(

rust/crates/runtime/src/mcp_stdio.rs

@@ -360,8 +360,10 @@ impl McpServerManagerError {
     }
 
     fn recoverable(&self) -> bool {
-        !matches!(self.lifecycle_phase(), McpLifecyclePhase::InitializeHandshake)
-            && matches!(self, Self::Transport { .. } | Self::Timeout { .. })
+        !matches!(
+            self.lifecycle_phase(),
+            McpLifecyclePhase::InitializeHandshake
+        ) && matches!(self, Self::Transport { .. } | Self::Timeout { .. })
     }
 
     fn discovery_failure(&self, server_name: &str) -> McpDiscoveryFailure {
@@ -417,10 +419,9 @@ impl McpServerManagerError {
                 ("method".to_string(), (*method).to_string()),
                 ("timeout_ms".to_string(), timeout_ms.to_string()),
             ]),
-            Self::UnknownTool { qualified_name } => BTreeMap::from([(
-                "qualified_tool".to_string(),
-                qualified_name.clone(),
-            )]),
+            Self::UnknownTool { qualified_name } => {
+                BTreeMap::from([("qualified_tool".to_string(), qualified_name.clone())])
+            }
             Self::UnknownServer { server_name } => {
                 BTreeMap::from([("server".to_string(), server_name.clone())])
             }
@@ -1425,11 +1426,10 @@ mod tests {
     use crate::mcp_client::McpClientBootstrap;
 
     use super::{
-        spawn_mcp_stdio_process, JsonRpcId, JsonRpcRequest, JsonRpcResponse,
-        McpInitializeClientInfo, McpInitializeParams, McpInitializeResult, McpInitializeServerInfo,
-        McpListToolsResult, McpReadResourceParams, McpReadResourceResult, McpServerManager,
-        McpServerManagerError, McpStdioProcess, McpTool, McpToolCallParams,
-        unsupported_server_failed_server,
+        spawn_mcp_stdio_process, unsupported_server_failed_server, JsonRpcId, JsonRpcRequest,
+        JsonRpcResponse, McpInitializeClientInfo, McpInitializeParams, McpInitializeResult,
+        McpInitializeServerInfo, McpListToolsResult, McpReadResourceParams, McpReadResourceResult,
+        McpServerManager, McpServerManagerError, McpStdioProcess, McpTool, McpToolCallParams,
     };
     use crate::McpLifecyclePhase;
 
@@ -2698,7 +2698,10 @@ mod tests {
             );
             assert!(!report.failed_servers[0].recoverable);
             assert_eq!(
-                report.failed_servers[0].context.get("method").map(String::as_str),
+                report.failed_servers[0]
+                    .context
+                    .get("method")
+                    .map(String::as_str),
                 Some("initialize")
             );
             assert!(report.failed_servers[0].error.contains("initialize"));

rust/crates/runtime/src/session_control.rs

@@ -4,7 +4,6 @@ use std::fs;
 use std::path::{Path, PathBuf};
 use std::time::UNIX_EPOCH;
 
-
 use crate::session::{Session, SessionError};
 
 pub const PRIMARY_SESSION_EXTENSION: &str = "jsonl";

rust/crates/runtime/src/task_packet.rs

@@ -66,11 +66,7 @@ pub fn validate_packet(packet: TaskPacket) -> Result<ValidatedPacket, TaskPacket
         &packet.reporting_contract,
         &mut errors,
     );
-    validate_required(
-        "escalation_policy",
-        &packet.escalation_policy,
-        &mut errors,
-    );
+    validate_required("escalation_policy", &packet.escalation_policy, &mut errors);
 
     for (index, test) in packet.acceptance_tests.iter().enumerate() {
         if test.trim().is_empty() {
@@ -146,9 +142,9 @@ mod tests {
         assert!(error
             .errors()
             .contains(&"repo must not be empty".to_string()));
-        assert!(error.errors().contains(
-            &"acceptance_tests contains an empty value at index 1".to_string()
-        ));
+        assert!(error
+            .errors()
+            .contains(&"acceptance_tests contains an empty value at index 1".to_string()));
     }
 
     #[test]

rust/crates/runtime/src/task_registry.rs

@@ -76,11 +76,7 @@ impl TaskRegistry {
     }
 
     pub fn create(&self, prompt: &str, description: Option<&str>) -> Task {
-        self.create_task(
-            prompt.to_owned(),
-            description.map(str::to_owned),
-            None,
-        )
+        self.create_task(prompt.to_owned(), description.map(str::to_owned), None)
     }
 
     pub fn create_from_packet(

rust/crates/runtime/src/worker_boot.rs

@@ -257,7 +257,9 @@ impl WorkerRegistry {
             let prompt_preview = prompt_preview(worker.last_prompt.as_deref().unwrap_or_default());
             let message = match observation.target {
                 WorkerPromptTarget::Shell => {
-                    format!("worker prompt landed in shell instead of coding agent: {prompt_preview}")
+                    format!(
+                        "worker prompt landed in shell instead of coding agent: {prompt_preview}"
+                    )
                 }
                 WorkerPromptTarget::WrongTarget => format!(
                     "worker prompt landed in the wrong target instead of {}: {}",
@@ -312,7 +314,9 @@ impl WorkerRegistry {
             worker.last_error = None;
         }
 
-        if detect_ready_for_prompt(screen_text, &lowered) && worker.status != WorkerStatus::ReadyForPrompt {
+        if detect_ready_for_prompt(screen_text, &lowered)
+            && worker.status != WorkerStatus::ReadyForPrompt
+        {
             worker.status = WorkerStatus::ReadyForPrompt;
             worker.prompt_in_flight = false;
             if matches!(
@@ -412,7 +416,10 @@ impl WorkerRegistry {
             worker_id: worker.worker_id.clone(),
             status: worker.status,
             ready: worker.status == WorkerStatus::ReadyForPrompt,
-            blocked: matches!(worker.status, WorkerStatus::TrustRequired | WorkerStatus::Failed),
+            blocked: matches!(
+                worker.status,
+                WorkerStatus::TrustRequired | WorkerStatus::Failed
+            ),
             replay_prompt_ready: worker.replay_prompt.is_some(),
             last_error: worker.last_error.clone(),
         })

rust/crates/rusty-claude-cli/tests/output_format_contract.rs

@@ -0,0 +1,449 @@
+use std::fs;
+use std::io::{Read, Write};
+use std::net::TcpListener;
+use std::path::{Path, PathBuf};
+use std::process::{Command, Output};
+use std::sync::atomic::{AtomicU64, Ordering};
+use std::thread;
+use std::time::{SystemTime, UNIX_EPOCH};
+
+use mock_anthropic_service::{MockAnthropicService, SCENARIO_PREFIX};
+use serde_json::{json, Value};
+
+static TEMP_COUNTER: AtomicU64 = AtomicU64::new(0);
+
+#[test]
+fn help_emits_json_when_requested() {
+    let root = unique_temp_dir("help-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "help"], &envs);
+
+    assert_eq!(parsed["kind"], "help");
+    assert!(parsed["message"]
+        .as_str()
+        .expect("help message")
+        .contains("Usage:"));
+}
+
+#[test]
+fn version_emits_json_when_requested() {
+    let root = unique_temp_dir("version-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "version"], &envs);
+
+    assert_eq!(parsed["kind"], "version");
+    assert_eq!(parsed["version"], env!("CARGO_PKG_VERSION"));
+}
+
+#[test]
+fn status_emits_json_when_requested() {
+    let root = unique_temp_dir("status-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "status"], &envs);
+
+    assert_eq!(parsed["kind"], "status");
+    assert!(parsed["workspace"]["cwd"].as_str().is_some());
+}
+
+#[test]
+fn sandbox_emits_json_when_requested() {
+    let root = unique_temp_dir("sandbox-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "sandbox"], &envs);
+
+    assert_eq!(parsed["kind"], "sandbox");
+    assert!(parsed["sandbox"].is_object());
+}
+
+#[test]
+fn dump_manifests_emits_json_when_requested() {
+    let root = unique_temp_dir("dump-manifests-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let upstream = write_upstream_fixture(&root);
+    let mut envs = isolated_env(&root);
+    envs.push((
+        "CLAUDE_CODE_UPSTREAM".to_string(),
+        upstream.display().to_string(),
+    ));
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "dump-manifests"], &envs);
+
+    assert_eq!(parsed["kind"], "dump-manifests");
+    assert_eq!(parsed["commands"], 1);
+    assert_eq!(parsed["tools"], 1);
+}
+
+#[test]
+fn bootstrap_plan_emits_json_when_requested() {
+    let root = unique_temp_dir("bootstrap-plan-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "bootstrap-plan"], &envs);
+
+    assert_eq!(parsed["kind"], "bootstrap-plan");
+    assert!(parsed["phases"].as_array().expect("phases array").len() > 1);
+}
+
+#[test]
+fn agents_emits_json_when_requested() {
+    let root = unique_temp_dir("agents-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "agents"], &envs);
+
+    assert_eq!(parsed["kind"], "agents");
+    assert!(!parsed["message"].as_str().expect("agents text").is_empty());
+}
+
+#[test]
+fn mcp_emits_json_when_requested() {
+    let root = unique_temp_dir("mcp-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "mcp"], &envs);
+
+    assert_eq!(parsed["kind"], "mcp");
+    assert!(parsed["message"]
+        .as_str()
+        .expect("mcp text")
+        .contains("MCP"));
+}
+
+#[test]
+fn skills_emits_json_when_requested() {
+    let root = unique_temp_dir("skills-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "skills"], &envs);
+
+    assert_eq!(parsed["kind"], "skills");
+    assert!(!parsed["message"].as_str().expect("skills text").is_empty());
+}
+
+#[test]
+fn system_prompt_emits_json_when_requested() {
+    let root = unique_temp_dir("system-prompt-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "system-prompt"], &envs);
+
+    assert_eq!(parsed["kind"], "system-prompt");
+    assert!(parsed["message"]
+        .as_str()
+        .expect("system prompt text")
+        .contains("You are an interactive agent"));
+}
+
+#[test]
+fn login_emits_json_when_requested() {
+    let root = unique_temp_dir("login-json");
+    let workspace = root.join("workspace");
+    fs::create_dir_all(&workspace).expect("workspace should exist");
+    let mut envs = isolated_env(&root);
+    let callback_port = reserve_port();
+    let token_port = reserve_port();
+
+    fs::create_dir_all(workspace.join(".claw")).expect("config dir should exist");
+    fs::write(
+        workspace.join(".claw").join("settings.json"),
+        json!({
+            "oauth": {
+                "clientId": "test-client",
+                "authorizeUrl": format!("http://127.0.0.1:{token_port}/authorize"),
+                "tokenUrl": format!("http://127.0.0.1:{token_port}/token"),
+                "callbackPort": callback_port,
+                "scopes": ["user:test"]
+            }
+        })
+        .to_string(),
+    )
+    .expect("oauth config should write");
+
+    let token_server = thread::spawn(move || {
+        let listener = TcpListener::bind(("127.0.0.1", token_port)).expect("token server bind");
+        let (mut stream, _) = listener.accept().expect("token request");
+        let mut request = [0_u8; 4096];
+        let _ = stream
+            .read(&mut request)
+            .expect("token request should read");
+        let body = json!({
+            "access_token": "test-access-token",
+            "refresh_token": "test-refresh-token",
+            "expires_at": 9_999_999_999_u64,
+            "scopes": ["user:test"]
+        })
+        .to_string();
+        let response = format!(
+            "HTTP/1.1 200 OK\r\ncontent-type: application/json\r\ncontent-length: {}\r\nconnection: close\r\n\r\n{}",
+            body.len(),
+            body
+        );
+        stream
+            .write_all(response.as_bytes())
+            .expect("token response should write");
+    });
+
+    let bin_dir = root.join("bin");
+    fs::create_dir_all(&bin_dir).expect("bin dir should exist");
+    let opener_path = bin_dir.join("xdg-open");
+    fs::write(
+        &opener_path,
+        format!(
+            "#!/usr/bin/env python3\nimport http.client\nimport sys\nimport urllib.parse\nurl = sys.argv[1]\nquery = urllib.parse.parse_qs(urllib.parse.urlparse(url).query)\nstate = query['state'][0]\nconn = http.client.HTTPConnection('127.0.0.1', {callback_port}, timeout=5)\nconn.request('GET', f\"/callback?code=test-code&state={{urllib.parse.quote(state)}}\")\nresp = conn.getresponse()\nresp.read()\nconn.close()\n"
+        ),
+    )
+    .expect("xdg-open wrapper should write");
+    #[cfg(unix)]
+    {
+        use std::os::unix::fs::PermissionsExt;
+        let mut permissions = fs::metadata(&opener_path)
+            .expect("wrapper metadata")
+            .permissions();
+        permissions.set_mode(0o755);
+        fs::set_permissions(&opener_path, permissions).expect("wrapper permissions");
+    }
+    let original_path = envs
+        .iter()
+        .find(|(key, _)| key == "PATH")
+        .map(|(_, value)| value.clone())
+        .unwrap_or_default();
+    for (key, value) in &mut envs {
+        if key == "PATH" {
+            *value = format!("{}:{original_path}", bin_dir.display());
+        }
+    }
+
+    let parsed = assert_json_command(&workspace, &["--output-format", "json", "login"], &envs);
+
+    token_server.join().expect("token server should finish");
+    assert_eq!(parsed["kind"], "login");
+    assert_eq!(parsed["callback_port"], callback_port);
+}
+
+#[test]
+fn logout_emits_json_when_requested() {
+    let root = unique_temp_dir("logout-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&root, &["--output-format", "json", "logout"], &envs);
+
+    assert_eq!(parsed["kind"], "logout");
+    assert!(parsed["message"]
+        .as_str()
+        .expect("logout text")
+        .contains("cleared"));
+}
+
+#[test]
+fn init_emits_json_when_requested() {
+    let root = unique_temp_dir("init-json");
+    let workspace = root.join("workspace");
+    fs::create_dir_all(&workspace).expect("workspace should exist");
+    let envs = isolated_env(&root);
+
+    let parsed = assert_json_command(&workspace, &["--output-format", "json", "init"], &envs);
+
+    assert_eq!(parsed["kind"], "init");
+    assert!(workspace.join("CLAUDE.md").exists());
+}
+
+#[test]
+fn prompt_subcommand_emits_json_when_requested() {
+    let root = unique_temp_dir("prompt-subcommand-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let mut envs = isolated_env(&root);
+    let runtime = tokio::runtime::Runtime::new().expect("tokio runtime should build");
+    let server = runtime
+        .block_on(MockAnthropicService::spawn())
+        .expect("mock service should start");
+    envs.push(("ANTHROPIC_API_KEY".to_string(), "test-key".to_string()));
+    envs.push(("ANTHROPIC_BASE_URL".to_string(), server.base_url()));
+
+    let prompt = format!("{SCENARIO_PREFIX}streaming_text");
+    let args = vec![
+        "--model".to_string(),
+        "sonnet".to_string(),
+        "--permission-mode".to_string(),
+        "read-only".to_string(),
+        "--output-format".to_string(),
+        "json".to_string(),
+        "prompt".to_string(),
+        prompt,
+    ];
+    let output = run_claw_with_env_owned(&root, &args, &envs);
+    let parsed = parse_json_stdout(&output);
+
+    assert_eq!(parsed["model"], "claude-sonnet-4-6");
+    assert!(parsed["message"]
+        .as_str()
+        .expect("assistant text")
+        .contains("streaming"));
+}
+
+#[test]
+fn bare_prompt_mode_emits_json_when_requested() {
+    let root = unique_temp_dir("bare-prompt-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let mut envs = isolated_env(&root);
+    let runtime = tokio::runtime::Runtime::new().expect("tokio runtime should build");
+    let server = runtime
+        .block_on(MockAnthropicService::spawn())
+        .expect("mock service should start");
+    envs.push(("ANTHROPIC_API_KEY".to_string(), "test-key".to_string()));
+    envs.push(("ANTHROPIC_BASE_URL".to_string(), server.base_url()));
+
+    let prompt = format!("{SCENARIO_PREFIX}streaming_text");
+    let args = vec![
+        "--model".to_string(),
+        "sonnet".to_string(),
+        "--permission-mode".to_string(),
+        "read-only".to_string(),
+        "--output-format".to_string(),
+        "json".to_string(),
+        prompt,
+    ];
+    let output = run_claw_with_env_owned(&root, &args, &envs);
+    let parsed = parse_json_stdout(&output);
+
+    assert_eq!(parsed["model"], "claude-sonnet-4-6");
+    assert!(parsed["message"]
+        .as_str()
+        .expect("assistant text")
+        .contains("streaming"));
+}
+
+#[test]
+fn resume_restore_emits_json_when_requested() {
+    let root = unique_temp_dir("resume-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+    let envs = isolated_env(&root);
+    let session_path = root.join("session.jsonl");
+    fs::write(
+        &session_path,
+        "{\"type\":\"session_meta\",\"version\":3,\"session_id\":\"resume-json\",\"created_at_ms\":0,\"updated_at_ms\":0}\n{\"type\":\"message\",\"message\":{\"role\":\"user\",\"blocks\":[{\"type\":\"text\",\"text\":\"hello\"}]}}\n",
+    )
+    .expect("session should write");
+
+    let args = vec![
+        "--output-format".to_string(),
+        "json".to_string(),
+        "--resume".to_string(),
+        session_path.display().to_string(),
+    ];
+    let output = run_claw_with_env_owned(&root, &args, &envs);
+    let parsed = parse_json_stdout(&output);
+
+    assert_eq!(parsed["kind"], "resume");
+    assert_eq!(parsed["messages"], 1);
+}
+
+fn assert_json_command(current_dir: &Path, args: &[&str], envs: &[(String, String)]) -> Value {
+    let output = run_claw_with_env(current_dir, args, envs);
+    parse_json_stdout(&output)
+}
+
+fn parse_json_stdout(output: &Output) -> Value {
+    assert!(
+        output.status.success(),
+        "stdout:\n{}\n\nstderr:\n{}",
+        String::from_utf8_lossy(&output.stdout),
+        String::from_utf8_lossy(&output.stderr)
+    );
+    serde_json::from_slice(&output.stdout).expect("stdout should be json")
+}
+
+fn run_claw_with_env(current_dir: &Path, args: &[&str], envs: &[(String, String)]) -> Output {
+    let owned_args = args
+        .iter()
+        .map(|value| (*value).to_string())
+        .collect::<Vec<_>>();
+    run_claw_with_env_owned(current_dir, &owned_args, envs)
+}
+
+fn run_claw_with_env_owned(
+    current_dir: &Path,
+    args: &[String],
+    envs: &[(String, String)],
+) -> Output {
+    let mut command = Command::new(env!("CARGO_BIN_EXE_claw"));
+    command.current_dir(current_dir).args(args).env_clear();
+    for (key, value) in envs {
+        command.env(key, value);
+    }
+    command.output().expect("claw should launch")
+}
+
+fn isolated_env(root: &Path) -> Vec<(String, String)> {
+    let config_home = root.join("config-home");
+    let home = root.join("home");
+    fs::create_dir_all(&config_home).expect("config home should exist");
+    fs::create_dir_all(&home).expect("home should exist");
+    vec![
+        (
+            "CLAW_CONFIG_HOME".to_string(),
+            config_home.display().to_string(),
+        ),
+        ("HOME".to_string(), home.display().to_string()),
+        (
+            "PATH".to_string(),
+            std::env::var("PATH").unwrap_or_else(|_| "/usr/bin:/bin".to_string()),
+        ),
+        ("NO_COLOR".to_string(), "1".to_string()),
+    ]
+}
+
+fn write_upstream_fixture(root: &Path) -> PathBuf {
+    let upstream = root.join("claw-code");
+    let src = upstream.join("src");
+    let entrypoints = src.join("entrypoints");
+    fs::create_dir_all(&entrypoints).expect("upstream entrypoints dir should exist");
+    fs::write(
+        src.join("commands.ts"),
+        "import FooCommand from './commands/foo'\n",
+    )
+    .expect("commands fixture should write");
+    fs::write(
+        src.join("tools.ts"),
+        "import ReadTool from './tools/read'\n",
+    )
+    .expect("tools fixture should write");
+    fs::write(
+        entrypoints.join("cli.tsx"),
+        "if (args[0] === '--version') {}\nstartupProfiler()\n",
+    )
+    .expect("cli fixture should write");
+    upstream
+}
+
+fn reserve_port() -> u16 {
+    let listener = TcpListener::bind(("127.0.0.1", 0)).expect("ephemeral port should bind");
+    let port = listener.local_addr().expect("local addr").port();
+    drop(listener);
+    port
+}
+
+fn unique_temp_dir(label: &str) -> PathBuf {
+    let millis = SystemTime::now()
+        .duration_since(UNIX_EPOCH)
+        .expect("clock should be after epoch")
+        .as_millis();
+    let counter = TEMP_COUNTER.fetch_add(1, Ordering::Relaxed);
+    std::env::temp_dir().join(format!(
+        "claw-output-format-{label}-{}-{millis}-{counter}",
+        std::process::id()
+    ))
+}

rust/crates/rusty-claude-cli/tests/resume_slash_commands.rs

@@ -7,6 +7,7 @@ use std::time::{SystemTime, UNIX_EPOCH};
 
 use runtime::ContentBlock;
 use runtime::Session;
+use serde_json::Value;
 
 static TEMP_COUNTER: AtomicU64 = AtomicU64::new(0);
 
@@ -221,6 +222,52 @@ fn resume_latest_restores_the_most_recent_managed_session() {
     assert!(stdout.contains(newer_path.to_str().expect("utf8 path")));
 }
 
+#[test]
+fn resumed_status_command_emits_structured_json_when_requested() {
+    // given
+    let temp_dir = unique_temp_dir("resume-status-json");
+    fs::create_dir_all(&temp_dir).expect("temp dir should exist");
+    let session_path = temp_dir.join("session.jsonl");
+
+    let mut session = Session::new();
+    session
+        .push_user_text("resume status json fixture")
+        .expect("session write should succeed");
+    session
+        .save_to_path(&session_path)
+        .expect("session should persist");
+
+    // when
+    let output = run_claw(
+        &temp_dir,
+        &[
+            "--output-format",
+            "json",
+            "--resume",
+            session_path.to_str().expect("utf8 path"),
+            "/status",
+        ],
+    );
+
+    // then
+    assert!(
+        output.status.success(),
+        "stdout:\n{}\n\nstderr:\n{}",
+        String::from_utf8_lossy(&output.stdout),
+        String::from_utf8_lossy(&output.stderr)
+    );
+
+    let stdout = String::from_utf8(output.stdout).expect("stdout should be utf8");
+    let parsed: Value =
+        serde_json::from_str(stdout.trim()).expect("resume status output should be json");
+    assert_eq!(parsed["kind"], "status");
+    assert_eq!(parsed["messages"], 1);
+    assert_eq!(
+        parsed["workspace"]["session"],
+        session_path.to_str().expect("utf8 path")
+    );
+}
+
 fn run_claw(current_dir: &Path, args: &[&str]) -> Output {
     run_claw_with_env(current_dir, args, &[])
 }

rust/crates/tools/src/lane_completion.rs

@@ -16,7 +16,7 @@ use runtime::{
 use crate::AgentOutput;
 
 /// Detects if a lane should be automatically marked as completed.
-/// 
+///
 /// Returns `Some(LaneContext)` with `completed = true` if all conditions met,
 /// `None` if lane should remain active.
 #[allow(dead_code)]
@@ -29,29 +29,29 @@ pub(crate) fn detect_lane_completion(
     if output.error.is_some() {
         return None;
     }
-    
+
     // Must have finished status
     if !output.status.eq_ignore_ascii_case("completed")
         && !output.status.eq_ignore_ascii_case("finished")
     {
         return None;
     }
-    
+
     // Must have no current blocker
     if output.current_blocker.is_some() {
         return None;
     }
-    
+
     // Must have green tests
     if !test_green {
         return None;
     }
-    
+
     // Must have pushed code
     if !has_pushed {
         return None;
     }
-    
+
     // All conditions met — create completed context
     Some(LaneContext {
         lane_id: output.agent_id.clone(),
@@ -67,9 +67,7 @@ pub(crate) fn detect_lane_completion(
 
 /// Evaluates policy actions for a completed lane.
 #[allow(dead_code)]
-pub(crate) fn evaluate_completed_lane(
-    context: &LaneContext,
-) -> Vec<PolicyAction> {
+pub(crate) fn evaluate_completed_lane(context: &LaneContext) -> Vec<PolicyAction> {
     let engine = PolicyEngine::new(vec![
         PolicyRule::new(
             "closeout-completed-lane",
@@ -87,7 +85,7 @@ pub(crate) fn evaluate_completed_lane(
             5,
         ),
     ]);
-    
+
     evaluate(&engine, context)
 }
 
@@ -114,53 +112,53 @@ mod tests {
             error: None,
         }
     }
-    
+
     #[test]
     fn detects_completion_when_all_conditions_met() {
         let output = test_output();
         let result = detect_lane_completion(&output, true, true);
-        
+
         assert!(result.is_some());
         let context = result.unwrap();
         assert!(context.completed);
         assert_eq!(context.green_level, 3);
         assert_eq!(context.blocker, LaneBlocker::None);
     }
-    
+
     #[test]
     fn no_completion_when_error_present() {
         let mut output = test_output();
         output.error = Some("Build failed".to_string());
-        
+
         let result = detect_lane_completion(&output, true, true);
         assert!(result.is_none());
     }
-    
+
     #[test]
     fn no_completion_when_not_finished() {
         let mut output = test_output();
         output.status = "Running".to_string();
-        
+
         let result = detect_lane_completion(&output, true, true);
         assert!(result.is_none());
     }
-    
+
     #[test]
     fn no_completion_when_tests_not_green() {
         let output = test_output();
-        
+
         let result = detect_lane_completion(&output, false, true);
         assert!(result.is_none());
     }
-    
+
     #[test]
     fn no_completion_when_not_pushed() {
         let output = test_output();
-        
+
         let result = detect_lane_completion(&output, true, false);
         assert!(result.is_none());
     }
-    
+
     #[test]
     fn evaluate_triggers_closeout_for_completed_lane() {
         let context = LaneContext {
@@ -173,9 +171,9 @@ mod tests {
             completed: true,
             reconciled: false,
         };
-        
+
         let actions = evaluate_completed_lane(&context);
-        
+
         assert!(actions.contains(&PolicyAction::CloseoutLane));
         assert!(actions.contains(&PolicyAction::CleanupSession));
     }

rust/crates/tools/src/lib.rs

@@ -17,7 +17,6 @@ use runtime::{
     permission_enforcer::{EnforcementResult, PermissionEnforcer},
     read_file,
     summary_compression::compress_summary_text,
-    TaskPacket,
     task_registry::TaskRegistry,
     team_cron_registry::{CronRegistry, TeamRegistry},
     worker_boot::{WorkerReadySnapshot, WorkerRegistry},
@@ -25,7 +24,7 @@ use runtime::{
     BranchFreshness, ContentBlock, ConversationMessage, ConversationRuntime, GrepSearchInput,
     LaneEvent, LaneEventBlocker, LaneEventName, LaneEventStatus, LaneFailureClass,
     McpDegradedReport, MessageRole, PermissionMode, PermissionPolicy, PromptCacheEvent,
-    RuntimeError, Session, ToolError, ToolExecutor,
+    RuntimeError, Session, TaskPacket, ToolError, ToolExecutor,
 };
 use serde::{Deserialize, Serialize};
 use serde_json::{json, Value};
@@ -1878,27 +1877,25 @@ fn branch_divergence_output(
         dangerously_disable_sandbox: None,
         return_code_interpretation: Some("preflight_blocked:branch_divergence".to_string()),
         no_output_expected: Some(false),
-        structured_content: Some(vec![
-            serde_json::to_value(
-                LaneEvent::new(
-                    LaneEventName::BranchStaleAgainstMain,
-                    LaneEventStatus::Blocked,
-                    iso8601_now(),
-                )
-                    .with_failure_class(LaneFailureClass::BranchDivergence)
-                    .with_detail(stderr.clone())
-                    .with_data(json!({
-                        "branch": branch,
-                        "mainRef": main_ref,
-                        "commitsBehind": commits_behind,
-                        "commitsAhead": commits_ahead,
-                        "missingCommits": missing_fixes,
-                        "blockedCommand": command,
-                        "recommendedAction": format!("merge or rebase {main_ref} before workspace tests")
-                    })),
+        structured_content: Some(vec![serde_json::to_value(
+            LaneEvent::new(
+                LaneEventName::BranchStaleAgainstMain,
+                LaneEventStatus::Blocked,
+                iso8601_now(),
             )
-            .expect("lane event should serialize"),
-        ]),
+            .with_failure_class(LaneFailureClass::BranchDivergence)
+            .with_detail(stderr.clone())
+            .with_data(json!({
+                "branch": branch,
+                "mainRef": main_ref,
+                "commitsBehind": commits_behind,
+                "commitsAhead": commits_ahead,
+                "missingCommits": missing_fixes,
+                "blockedCommand": command,
+                "recommendedAction": format!("merge or rebase {main_ref} before workspace tests")
+            })),
+        )
+        .expect("lane event should serialize")]),
         persisted_output_path: None,
         persisted_output_size: None,
         sandbox_status: None,
@@ -3297,12 +3294,12 @@ fn persist_agent_terminal_state(
     next_manifest.current_blocker = blocker.clone();
     next_manifest.error = error;
     if let Some(blocker) = blocker {
-        next_manifest.lane_events.push(
-            LaneEvent::blocked(iso8601_now(), &blocker),
-        );
-        next_manifest.lane_events.push(
-            LaneEvent::failed(iso8601_now(), &blocker),
-        );
+        next_manifest
+            .lane_events
+            .push(LaneEvent::blocked(iso8601_now(), &blocker));
+        next_manifest
+            .lane_events
+            .push(LaneEvent::failed(iso8601_now(), &blocker));
     } else {
         next_manifest.current_blocker = None;
         let compressed_detail = result
@@ -4952,8 +4949,8 @@ mod tests {
         agent_permission_policy, allowed_tools_for_subagent, classify_lane_failure,
         execute_agent_with_spawn, execute_tool, final_assistant_text, mvp_tool_specs,
         permission_mode_from_plugin, persist_agent_terminal_state, push_output_block,
-        run_task_packet, AgentInput, AgentJob, GlobalToolRegistry, LaneEventName,
-        LaneFailureClass, SubagentToolExecutor,
+        run_task_packet, AgentInput, AgentJob, GlobalToolRegistry, LaneEventName, LaneFailureClass,
+        SubagentToolExecutor,
     };
     use api::OutputContentBlock;
     use runtime::{
@@ -5977,7 +5974,10 @@ mod tests {
                 "gateway routing rejected the request",
                 LaneFailureClass::GatewayRouting,
             ),
-            ("tool failed: denied tool execution from hook", LaneFailureClass::ToolRuntime),
+            (
+                "tool failed: denied tool execution from hook",
+                LaneFailureClass::ToolRuntime,
+            ),
             ("thread creation failed", LaneFailureClass::Infra),
         ];
 
@@ -6000,11 +6000,17 @@ mod tests {
             (LaneEventName::MergeReady, "lane.merge.ready"),
             (LaneEventName::Finished, "lane.finished"),
             (LaneEventName::Failed, "lane.failed"),
-            (LaneEventName::BranchStaleAgainstMain, "branch.stale_against_main"),
+            (
+                LaneEventName::BranchStaleAgainstMain,
+                "branch.stale_against_main",
+            ),
         ];
 
         for (event, expected) in cases {
-            assert_eq!(serde_json::to_value(event).expect("serialize lane event"), json!(expected));
+            assert_eq!(
+                serde_json::to_value(event).expect("serialize lane event"),
+                json!(expected)
+            );
         }
     }