Clarify the resumed JSON parity audit record

The audit fix already landed, but the roadmap entry was split across two separate done items for /sandbox and inventory even though the underlying defect was one resumed-local-command JSON parity surface. Consolidating the note makes the machine-readable gap precise and keeps the backlog trail aligned with the actual fix scope.

Constraint: Preserve the existing issue ordering and backlog context around issues 23-24
Rejected: Leave the split entries as-is | obscures that one parity bug covered the same resumed JSON dispatch path
Confidence: high
Scope-risk: narrow
Reversibility: clean
Directive: Record future parity audits as one backlog item per underlying contract gap, not per individual command symptom
Tested: Existing green verification from HEAD remains applicable; docs-only wording update
Not-tested: No additional code-path verification required for this wording-only change

ROADMAP.md

@@ -307,6 +307,11 @@ Priority order: P0 = blocks CI/green state, P1 = blocks integration wiring, P2 =
 18. **Context-window preflight gap** — **done**: provider request sizing now emits `context_window_blocked` before oversized requests leave the process, using a model-context registry instead of the old naive max-token heuristic.
 19. **Subcommand help falls through into runtime/API path** — **done**: `claw doctor --help`, `claw status --help`, `claw sandbox --help`, and nested `mcp`/`skills` help are now intercepted locally without runtime/provider startup, with regression tests covering the direct CLI paths.
 20. **Session state classification gap (working vs blocked vs finished vs truly stale)** — **done**: agent manifests now derive machine states such as `working`, `blocked_background_job`, `blocked_merge_conflict`, `degraded_mcp`, `interrupted_transport`, `finished_pending_report`, and `finished_cleanable`, and terminal-state persistence records commit provenance plus derived state so downstream monitoring can distinguish quiet progress from truly idle sessions.
+21. **Resumed `/status` JSON parity gap** — dogfooding shows fresh `claw status --output-format json` now emits structured JSON, but resumed slash-command status still leaks through a text-shaped path in at least one dispatch path. Local CI-equivalent repro fails `rust/crates/rusty-claude-cli/tests/resume_slash_commands.rs::resumed_status_command_emits_structured_json_when_requested` with `expected value at line 1 column 1`, so resumed automation can receive text where JSON was explicitly requested. **Action:** unify fresh vs resumed `/status` rendering through one output-format contract and add regression coverage so resumed JSON output is guaranteed valid.
+22. **Opaque failure surface for session/runtime crashes** — repeated dogfood-facing failures can currently collapse to generic wrappers like `Something went wrong while processing your request. Please try again, or use /new to start a fresh session.` without exposing whether the fault was provider auth, session corruption, slash-command dispatch, render failure, or transport/runtime panic. This blocks fast self-recovery and turns actionable clawability bugs into blind retries. **Action:** preserve a short user-safe failure class (`provider_auth`, `session_load`, `command_dispatch`, `render`, `runtime_panic`, etc.), attach a local trace/session id, and ensure operators can jump from the chat-visible error to the exact failure log quickly.
+23. **`doctor --output-format json` check-level structure gap** — **done**: `claw doctor --output-format json` now keeps the human-readable `message`/`report` while also emitting structured per-check diagnostics (`name`, `status`, `summary`, `details`, plus typed fields like workspace paths and sandbox fallback data), with regression coverage in `output_format_contract.rs`.
+24. **Plugin lifecycle init/shutdown test flakes under workspace-parallel execution** — dogfooding surfaced that `build_runtime_runs_plugin_lifecycle_init_and_shutdown` can fail under `cargo test --workspace` while passing in isolation because sibling tests race on tempdir-backed shell init script paths. This is test brittleness rather than a code-path regression, but it still destabilizes CI confidence and wastes diagnosis cycles. **Action:** isolate temp resources per test robustly (unique dirs + no shared cwd assumptions), audit cleanup timing, and add a regression guard so the plugin lifecycle test remains stable under parallel workspace execution.
+26. **Resumed local-command JSON parity gap** — **done**: direct `claw --output-format json` already had structured renderers for `sandbox`, `mcp`, `skills`, `version`, and `init`, but resumed `claw --output-format json --resume <session> /…` paths still fell back to prose because resumed slash dispatch only emitted JSON for `/status`. Resumed `/sandbox`, `/mcp`, `/skills`, `/version`, and `/init` now reuse the same JSON envelopes as their direct CLI counterparts, with regression coverage in `rust/crates/rusty-claude-cli/tests/resume_slash_commands.rs` and `rust/crates/rusty-claude-cli/tests/output_format_contract.rs`.
 **P3 — Swarm efficiency**
 13. Swarm branch-lock protocol — **done**: `branch_lock::detect_branch_lock_collisions()` now detects same-branch/same-scope and nested-module collisions before parallel lanes drift into duplicate implementation
 14. Commit provenance / worktree-aware push events — **done**: lane event provenance now includes branch/worktree/superseded/canonical lineage metadata, and manifest persistence de-dupes superseded commit events before downstream consumers render them

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 +71,66 @@ 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::RetriesExhausted { .. } => "provider_retry_exhausted",
+            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 { .. } if self.is_generic_fatal_wrapper() => "provider_internal",
+            Self::Api { .. } => "provider_error",
+            Self::Http(_) | Self::InvalidSseFrame(_) | Self::BackoffOverflow { .. } => {
+                "provider_transport"
+            }
+            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 {
@@ -102,14 +168,24 @@ 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}")
+            } => {
+                if let (Some(error_type), Some(message)) = (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}")
+                } else {
+                    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,
                 last_error,
@@ -151,3 +227,57 @@ 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_retry_exhausted");
+        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/commands/src/lib.rs

@@ -2187,6 +2187,27 @@ pub fn handle_agents_slash_command(args: Option<&str>, cwd: &Path) -> std::io::R
     }
 }
 
+pub fn handle_agents_slash_command_json(args: Option<&str>, cwd: &Path) -> std::io::Result<Value> {
+    if let Some(args) = normalize_optional_args(args) {
+        if let Some(help_path) = help_path_from_args(args) {
+            return Ok(match help_path.as_slice() {
+                [] => render_agents_usage_json(None),
+                _ => render_agents_usage_json(Some(&help_path.join(" "))),
+            });
+        }
+    }
+
+    match normalize_optional_args(args) {
+        None | Some("list") => {
+            let roots = discover_definition_roots(cwd, "agents");
+            let agents = load_agents_from_roots(&roots)?;
+            Ok(render_agents_report_json(cwd, &agents))
+        }
+        Some(args) if is_help_arg(args) => Ok(render_agents_usage_json(None)),
+        Some(args) => Ok(render_agents_usage_json(Some(args))),
+    }
+}
+
 pub fn handle_mcp_slash_command(
     args: Option<&str>,
     cwd: &Path,
@@ -3039,6 +3060,25 @@ fn render_agents_report(agents: &[AgentSummary]) -> String {
     lines.join("\n").trim_end().to_string()
 }
 
+fn render_agents_report_json(cwd: &Path, agents: &[AgentSummary]) -> Value {
+    let active = agents
+        .iter()
+        .filter(|agent| agent.shadowed_by.is_none())
+        .count();
+    json!({
+        "kind": "agents",
+        "action": "list",
+        "working_directory": cwd.display().to_string(),
+        "count": agents.len(),
+        "summary": {
+            "total": agents.len(),
+            "active": active,
+            "shadowed": agents.len().saturating_sub(active),
+        },
+        "agents": agents.iter().map(agent_summary_json).collect::<Vec<_>>(),
+    })
+}
+
 fn agent_detail(agent: &AgentSummary) -> String {
     let mut parts = vec![agent.name.clone()];
     if let Some(description) = &agent.description {
@@ -3327,6 +3367,19 @@ fn render_agents_usage(unexpected: Option<&str>) -> String {
     lines.join("\n")
 }
 
+fn render_agents_usage_json(unexpected: Option<&str>) -> Value {
+    json!({
+        "kind": "agents",
+        "action": "help",
+        "usage": {
+            "slash_command": "/agents [list|help]",
+            "direct_cli": "claw agents [list|help]",
+            "sources": [".claw/agents", "~/.claw/agents", "$CLAW_CONFIG_HOME/agents"],
+        },
+        "unexpected": unexpected,
+    })
+}
+
 fn render_skills_usage(unexpected: Option<&str>) -> String {
     let mut lines = vec![
         "Skills".to_string(),
@@ -3478,6 +3531,18 @@ fn definition_source_json(source: DefinitionSource) -> Value {
     })
 }
 
+fn agent_summary_json(agent: &AgentSummary) -> Value {
+    json!({
+        "name": &agent.name,
+        "description": &agent.description,
+        "model": &agent.model,
+        "reasoning_effort": &agent.reasoning_effort,
+        "source": definition_source_json(agent.source),
+        "active": agent.shadowed_by.is_none(),
+        "shadowed_by": agent.shadowed_by.map(definition_source_json),
+    })
+}
+
 fn skill_origin_id(origin: SkillOrigin) -> &'static str {
     match origin {
         SkillOrigin::SkillsDir => "skills_dir",
@@ -3686,8 +3751,9 @@ pub fn handle_slash_command(
 #[cfg(test)]
 mod tests {
     use super::{
-        handle_plugins_slash_command, handle_skills_slash_command_json, handle_slash_command,
-        load_agents_from_roots, load_skills_from_roots, render_agents_report,
+        handle_agents_slash_command_json, handle_plugins_slash_command,
+        handle_skills_slash_command_json, handle_slash_command, load_agents_from_roots,
+        load_skills_from_roots, render_agents_report, render_agents_report_json,
         render_mcp_report_json_for, render_plugins_report, render_skills_report,
         render_slash_command_help, render_slash_command_help_detail,
         resume_supported_slash_commands, slash_command_specs, suggest_slash_commands,
@@ -4363,6 +4429,72 @@ mod tests {
         let _ = fs::remove_dir_all(user_home);
     }
 
+    #[test]
+    fn renders_agents_reports_as_json() {
+        let workspace = temp_dir("agents-json-workspace");
+        let project_agents = workspace.join(".codex").join("agents");
+        let user_home = temp_dir("agents-json-home");
+        let user_agents = user_home.join(".codex").join("agents");
+
+        write_agent(
+            &project_agents,
+            "planner",
+            "Project planner",
+            "gpt-5.4",
+            "medium",
+        );
+        write_agent(
+            &project_agents,
+            "verifier",
+            "Verification agent",
+            "gpt-5.4-mini",
+            "high",
+        );
+        write_agent(
+            &user_agents,
+            "planner",
+            "User planner",
+            "gpt-5.4-mini",
+            "high",
+        );
+
+        let roots = vec![
+            (DefinitionSource::ProjectCodex, project_agents),
+            (DefinitionSource::UserCodex, user_agents),
+        ];
+        let report = render_agents_report_json(
+            &workspace,
+            &load_agents_from_roots(&roots).expect("agent roots should load"),
+        );
+
+        assert_eq!(report["kind"], "agents");
+        assert_eq!(report["action"], "list");
+        assert_eq!(report["working_directory"], workspace.display().to_string());
+        assert_eq!(report["count"], 3);
+        assert_eq!(report["summary"]["active"], 2);
+        assert_eq!(report["summary"]["shadowed"], 1);
+        assert_eq!(report["agents"][0]["name"], "planner");
+        assert_eq!(report["agents"][0]["model"], "gpt-5.4");
+        assert_eq!(report["agents"][0]["active"], true);
+        assert_eq!(report["agents"][1]["name"], "verifier");
+        assert_eq!(report["agents"][2]["name"], "planner");
+        assert_eq!(report["agents"][2]["active"], false);
+        assert_eq!(report["agents"][2]["shadowed_by"]["id"], "project_claw");
+
+        let help = handle_agents_slash_command_json(Some("help"), &workspace).expect("agents help");
+        assert_eq!(help["kind"], "agents");
+        assert_eq!(help["action"], "help");
+        assert_eq!(help["usage"]["direct_cli"], "claw agents [list|help]");
+
+        let unexpected = handle_agents_slash_command_json(Some("show planner"), &workspace)
+            .expect("agents usage");
+        assert_eq!(unexpected["action"], "help");
+        assert_eq!(unexpected["unexpected"], "show planner");
+
+        let _ = fs::remove_dir_all(workspace);
+        let _ = fs::remove_dir_all(user_home);
+    }
+
     #[test]
     fn lists_skills_from_project_and_user_roots() {
         let workspace = temp_dir("skills-workspace");

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

@@ -31,10 +31,10 @@ use api::{
 };
 
 use commands::{
-    handle_agents_slash_command, handle_mcp_slash_command, handle_mcp_slash_command_json,
-    handle_plugins_slash_command, handle_skills_slash_command, handle_skills_slash_command_json,
-    render_slash_command_help, resume_supported_slash_commands, slash_command_specs,
-    validate_slash_command_input, SlashCommand,
+    handle_agents_slash_command, handle_agents_slash_command_json, handle_mcp_slash_command,
+    handle_mcp_slash_command_json, handle_plugins_slash_command, handle_skills_slash_command,
+    handle_skills_slash_command_json, render_slash_command_help, resume_supported_slash_commands,
+    slash_command_specs, validate_slash_command_input, SlashCommand,
 };
 use compat_harness::{extract_manifest, UpstreamPaths};
 use init::initialize_repo;
@@ -51,7 +51,7 @@ use runtime::{
     Session, TokenUsage, ToolError, ToolExecutor, UsageTracker,
 };
 use serde::Deserialize;
-use serde_json::json;
+use serde_json::{json, Map, Value};
 use tools::{GlobalToolRegistry, RuntimeToolDefinition, ToolSearchOutput};
 
 const DEFAULT_MODEL: &str = "claude-opus-4-6";
@@ -870,6 +870,7 @@ struct DiagnosticCheck {
     level: DiagnosticLevel,
     summary: String,
     details: Vec<String>,
+    data: Map<String, Value>,
 }
 
 impl DiagnosticCheck {
@@ -879,6 +880,7 @@ impl DiagnosticCheck {
             level,
             summary: summary.into(),
             details: Vec::new(),
+            data: Map::new(),
         }
     }
 
@@ -886,6 +888,37 @@ impl DiagnosticCheck {
         self.details = details;
         self
     }
+
+    fn with_data(mut self, data: Map<String, Value>) -> Self {
+        self.data = data;
+        self
+    }
+
+    fn json_value(&self) -> Value {
+        let mut value = Map::from_iter([
+            (
+                "name".to_string(),
+                Value::String(self.name.to_ascii_lowercase()),
+            ),
+            (
+                "status".to_string(),
+                Value::String(self.level.label().to_string()),
+            ),
+            ("summary".to_string(), Value::String(self.summary.clone())),
+            (
+                "details".to_string(),
+                Value::Array(
+                    self.details
+                        .iter()
+                        .cloned()
+                        .map(Value::String)
+                        .collect::<Vec<_>>(),
+                ),
+            ),
+        ]);
+        value.extend(self.data.clone());
+        Value::Object(value)
+    }
 }
 
 #[derive(Debug, Clone, PartialEq, Eq)]
@@ -894,26 +927,29 @@ struct DoctorReport {
 }
 
 impl DoctorReport {
+    fn counts(&self) -> (usize, usize, usize) {
+        (
+            self.checks
+                .iter()
+                .filter(|check| check.level == DiagnosticLevel::Ok)
+                .count(),
+            self.checks
+                .iter()
+                .filter(|check| check.level == DiagnosticLevel::Warn)
+                .count(),
+            self.checks
+                .iter()
+                .filter(|check| check.level == DiagnosticLevel::Fail)
+                .count(),
+        )
+    }
+
     fn has_failures(&self) -> bool {
         self.checks.iter().any(|check| check.level.is_failure())
     }
 
     fn render(&self) -> String {
-        let ok_count = self
-            .checks
-            .iter()
-            .filter(|check| check.level == DiagnosticLevel::Ok)
-            .count();
-        let warn_count = self
-            .checks
-            .iter()
-            .filter(|check| check.level == DiagnosticLevel::Warn)
-            .count();
-        let fail_count = self
-            .checks
-            .iter()
-            .filter(|check| check.level == DiagnosticLevel::Fail)
-            .count();
+        let (ok_count, warn_count, fail_count) = self.counts();
         let mut lines = vec![
             "Doctor".to_string(),
             format!(
@@ -923,6 +959,28 @@ impl DoctorReport {
         lines.extend(self.checks.iter().map(render_diagnostic_check));
         lines.join("\n\n")
     }
+
+    fn json_value(&self) -> Value {
+        let report = self.render();
+        let (ok_count, warn_count, fail_count) = self.counts();
+        json!({
+            "kind": "doctor",
+            "message": report,
+            "report": report,
+            "has_failures": self.has_failures(),
+            "summary": {
+                "total": self.checks.len(),
+                "ok": ok_count,
+                "warnings": warn_count,
+                "failures": fail_count,
+            },
+            "checks": self
+                .checks
+                .iter()
+                .map(DiagnosticCheck::json_value)
+                .collect::<Vec<_>>(),
+        })
+    }
 }
 
 fn render_diagnostic_check(check: &DiagnosticCheck) -> String {
@@ -980,15 +1038,9 @@ fn run_doctor(output_format: CliOutputFormat) -> Result<(), Box<dyn std::error::
     let message = report.render();
     match output_format {
         CliOutputFormat::Text => println!("{message}"),
-        CliOutputFormat::Json => println!(
-            "{}",
-            serde_json::to_string_pretty(&json!({
-                "kind": "doctor",
-                "message": message,
-                "report": message,
-                "has_failures": report.has_failures(),
-            }))?
-        ),
+        CliOutputFormat::Json => {
+            println!("{}", serde_json::to_string_pretty(&report.json_value())?);
+        }
     }
     if report.has_failures() {
         return Err("doctor found failing checks".into());
@@ -996,6 +1048,7 @@ fn run_doctor(output_format: CliOutputFormat) -> Result<(), Box<dyn std::error::
     Ok(())
 }
 
+#[allow(clippy::too_many_lines)]
 fn check_auth_health() -> DiagnosticCheck {
     let api_key_present = env::var("ANTHROPIC_API_KEY")
         .ok()
@@ -1060,6 +1113,21 @@ fn check_auth_health() -> DiagnosticCheck {
                 },
             )
             .with_details(details)
+            .with_data(Map::from_iter([
+                ("api_key_present".to_string(), json!(api_key_present)),
+                ("auth_token_present".to_string(), json!(auth_token_present)),
+                ("saved_oauth_present".to_string(), json!(true)),
+                ("saved_oauth_expired".to_string(), json!(expired)),
+                (
+                    "saved_oauth_expires_at".to_string(),
+                    json!(token_set.expires_at),
+                ),
+                (
+                    "refresh_token_present".to_string(),
+                    json!(token_set.refresh_token.is_some()),
+                ),
+                ("scopes".to_string(), json!(token_set.scopes)),
+            ]))
         }
         Ok(None) => DiagnosticCheck::new(
             "Auth",
@@ -1082,12 +1150,31 @@ fn check_auth_health() -> DiagnosticCheck {
             } else {
                 "absent"
             }
-        )]),
+        )])
+        .with_data(Map::from_iter([
+            ("api_key_present".to_string(), json!(api_key_present)),
+            ("auth_token_present".to_string(), json!(auth_token_present)),
+            ("saved_oauth_present".to_string(), json!(false)),
+            ("saved_oauth_expired".to_string(), json!(false)),
+            ("saved_oauth_expires_at".to_string(), Value::Null),
+            ("refresh_token_present".to_string(), json!(false)),
+            ("scopes".to_string(), json!(Vec::<String>::new())),
+        ])),
         Err(error) => DiagnosticCheck::new(
             "Auth",
             DiagnosticLevel::Fail,
             format!("failed to inspect saved credentials: {error}"),
-        ),
+        )
+        .with_data(Map::from_iter([
+            ("api_key_present".to_string(), json!(api_key_present)),
+            ("auth_token_present".to_string(), json!(auth_token_present)),
+            ("saved_oauth_present".to_string(), Value::Null),
+            ("saved_oauth_expired".to_string(), Value::Null),
+            ("saved_oauth_expires_at".to_string(), Value::Null),
+            ("refresh_token_present".to_string(), Value::Null),
+            ("scopes".to_string(), Value::Null),
+            ("saved_oauth_error".to_string(), json!(error.to_string())),
+        ])),
     }
 }
 
@@ -1121,7 +1208,7 @@ fn check_config_health(
             } else {
                 details.extend(
                     discovered_paths
-                        .into_iter()
+                        .iter()
                         .map(|path| format!("Discovered file   {path}")),
                 );
             }
@@ -1139,6 +1226,22 @@ fn check_config_health(
                 },
             )
             .with_details(details)
+            .with_data(Map::from_iter([
+                ("discovered_files".to_string(), json!(discovered_paths)),
+                (
+                    "discovered_files_count".to_string(),
+                    json!(discovered_count),
+                ),
+                (
+                    "loaded_config_files".to_string(),
+                    json!(loaded_entries.len()),
+                ),
+                ("resolved_model".to_string(), json!(runtime_config.model())),
+                (
+                    "mcp_servers".to_string(),
+                    json!(runtime_config.mcp().servers().len()),
+                ),
+            ]))
         }
         Err(error) => DiagnosticCheck::new(
             "Config",
@@ -1149,10 +1252,21 @@ fn check_config_health(
             vec!["Discovered files  <none>".to_string()]
         } else {
             discovered_paths
-                .into_iter()
+                .iter()
                 .map(|path| format!("Discovered file   {path}"))
                 .collect()
-        }),
+        })
+        .with_data(Map::from_iter([
+            ("discovered_files".to_string(), json!(discovered_paths)),
+            (
+                "discovered_files_count".to_string(),
+                json!(discovered_count),
+            ),
+            ("loaded_config_files".to_string(), json!(0)),
+            ("resolved_model".to_string(), Value::Null),
+            ("mcp_servers".to_string(), Value::Null),
+            ("load_error".to_string(), json!(error.to_string())),
+        ])),
     }
 }
 
@@ -1194,6 +1308,38 @@ fn check_workspace_health(context: &StatusContext) -> DiagnosticCheck {
             context.memory_file_count, context.loaded_config_files, context.discovered_config_files
         ),
     ])
+    .with_data(Map::from_iter([
+        ("cwd".to_string(), json!(context.cwd.display().to_string())),
+        (
+            "project_root".to_string(),
+            json!(context
+                .project_root
+                .as_ref()
+                .map(|path| path.display().to_string())),
+        ),
+        ("in_git_repo".to_string(), json!(in_repo)),
+        ("git_branch".to_string(), json!(context.git_branch)),
+        (
+            "git_state".to_string(),
+            json!(context.git_summary.headline()),
+        ),
+        (
+            "changed_files".to_string(),
+            json!(context.git_summary.changed_files),
+        ),
+        (
+            "memory_file_count".to_string(),
+            json!(context.memory_file_count),
+        ),
+        (
+            "loaded_config_files".to_string(),
+            json!(context.loaded_config_files),
+        ),
+        (
+            "discovered_config_files".to_string(),
+            json!(context.discovered_config_files),
+        ),
+    ]))
 }
 
 fn check_sandbox_health(status: &runtime::SandboxStatus) -> DiagnosticCheck {
@@ -1224,9 +1370,43 @@ fn check_sandbox_health(status: &runtime::SandboxStatus) -> DiagnosticCheck {
         },
     )
     .with_details(details)
+    .with_data(Map::from_iter([
+        ("enabled".to_string(), json!(status.enabled)),
+        ("active".to_string(), json!(status.active)),
+        ("supported".to_string(), json!(status.supported)),
+        (
+            "namespace_supported".to_string(),
+            json!(status.namespace_supported),
+        ),
+        (
+            "namespace_active".to_string(),
+            json!(status.namespace_active),
+        ),
+        (
+            "network_supported".to_string(),
+            json!(status.network_supported),
+        ),
+        ("network_active".to_string(), json!(status.network_active)),
+        (
+            "filesystem_mode".to_string(),
+            json!(status.filesystem_mode.as_str()),
+        ),
+        (
+            "filesystem_active".to_string(),
+            json!(status.filesystem_active),
+        ),
+        ("allowed_mounts".to_string(), json!(status.allowed_mounts)),
+        ("in_container".to_string(), json!(status.in_container)),
+        (
+            "container_markers".to_string(),
+            json!(status.container_markers),
+        ),
+        ("fallback_reason".to_string(), json!(status.fallback_reason)),
+    ]))
 }
 
 fn check_system_health(cwd: &Path, config: Option<&runtime::RuntimeConfig>) -> DiagnosticCheck {
+    let default_model = config.and_then(runtime::RuntimeConfig::model);
     let mut details = vec![
         format!("OS               {} {}", env::consts::OS, env::consts::ARCH),
         format!("Working dir      {}", cwd.display()),
@@ -1234,7 +1414,7 @@ fn check_system_health(cwd: &Path, config: Option<&runtime::RuntimeConfig>) -> D
         format!("Build target     {}", BUILD_TARGET.unwrap_or("<unknown>")),
         format!("Git SHA          {}", GIT_SHA.unwrap_or("<unknown>")),
     ];
-    if let Some(model) = config.and_then(runtime::RuntimeConfig::model) {
+    if let Some(model) = default_model {
         details.push(format!("Default model    {model}"));
     }
     DiagnosticCheck::new(
@@ -1243,6 +1423,15 @@ fn check_system_health(cwd: &Path, config: Option<&runtime::RuntimeConfig>) -> D
         "captured local runtime metadata",
     )
     .with_details(details)
+    .with_data(Map::from_iter([
+        ("os".to_string(), json!(env::consts::OS)),
+        ("arch".to_string(), json!(env::consts::ARCH)),
+        ("working_dir".to_string(), json!(cwd.display().to_string())),
+        ("version".to_string(), json!(VERSION)),
+        ("build_target".to_string(), json!(BUILD_TARGET)),
+        ("git_sha".to_string(), json!(GIT_SHA)),
+        ("default_model".to_string(), json!(default_model)),
+    ]))
 }
 
 fn resume_command_can_absorb_token(current_command: &str, token: &str) -> bool {
@@ -1499,23 +1688,25 @@ fn print_system_prompt(
 }
 
 fn print_version(output_format: CliOutputFormat) -> Result<(), Box<dyn std::error::Error>> {
-    let report = render_version_report();
     match output_format {
-        CliOutputFormat::Text => println!("{report}"),
-        CliOutputFormat::Json => println!(
-            "{}",
-            serde_json::to_string_pretty(&json!({
-                "kind": "version",
-                "message": report,
-                "version": VERSION,
-                "git_sha": GIT_SHA,
-                "target": BUILD_TARGET,
-            }))?
-        ),
+        CliOutputFormat::Text => println!("{}", render_version_report()),
+        CliOutputFormat::Json => {
+            println!("{}", serde_json::to_string_pretty(&version_json_value())?);
+        }
     }
     Ok(())
 }
 
+fn version_json_value() -> serde_json::Value {
+    json!({
+        "kind": "version",
+        "message": render_version_report(),
+        "version": VERSION,
+        "git_sha": GIT_SHA,
+        "target": BUILD_TARGET,
+    })
+}
+
 fn resume_session(session_path: &Path, commands: &[String], output_format: CliOutputFormat) {
     let resolved_path = if session_path.exists() {
         session_path.to_path_buf()
@@ -1563,38 +1754,21 @@ fn resume_session(session_path: &Path, commands: &[String], output_format: CliOu
             Ok(ResumeCommandOutcome {
                 session: next_session,
                 message,
+                json,
             }) => {
                 session = next_session;
-                if let Some(message) = message {
-                    if output_format == CliOutputFormat::Json
-                        && matches!(command, SlashCommand::Status)
-                    {
-                        let tracker = UsageTracker::from_session(&session);
-                        let usage = tracker.cumulative_usage();
-                        let context = status_context(Some(&resolved_path)).expect("status context");
-                        let value = json!({
-                            "kind": "status",
-                            "messages": session.messages.len(),
-                            "turns": tracker.turns(),
-                            "latest_total": tracker.current_turn_usage().total_tokens(),
-                            "cumulative_input": usage.input_tokens,
-                            "cumulative_output": usage.output_tokens,
-                            "cumulative_total": usage.total_tokens(),
-                            "workspace": {
-                                "cwd": context.cwd,
-                                "project_root": context.project_root,
-                                "git_branch": context.git_branch,
-                                "git_state": context.git_summary.headline(),
-                                "session": context.session_path.as_ref().map_or_else(|| "live-repl".to_string(), |path| path.display().to_string()),
-                            }
-                        });
+                if output_format == CliOutputFormat::Json {
+                    if let Some(value) = json {
                         println!(
                             "{}",
-                            serde_json::to_string_pretty(&value).expect("status json")
+                            serde_json::to_string_pretty(&value)
+                                .expect("resume command json output")
                         );
-                    } else {
+                    } else if let Some(message) = message {
                         println!("{message}");
                     }
+                } else if let Some(message) = message {
+                    println!("{message}");
                 }
             }
             Err(error) => {
@@ -1609,6 +1783,7 @@ fn resume_session(session_path: &Path, commands: &[String], output_format: CliOu
 struct ResumeCommandOutcome {
     session: Session,
     message: Option<String>,
+    json: Option<serde_json::Value>,
 }
 
 #[derive(Debug, Clone)]
@@ -1943,6 +2118,7 @@ fn run_resume_command(
         SlashCommand::Help => Ok(ResumeCommandOutcome {
             session: session.clone(),
             message: Some(render_repl_help()),
+            json: None,
         }),
         SlashCommand::Compact => {
             let result = runtime::compact_session(
@@ -1959,6 +2135,7 @@ fn run_resume_command(
             Ok(ResumeCommandOutcome {
                 session: result.compacted_session,
                 message: Some(format_compact_report(removed, kept, skipped)),
+                json: None,
             })
         }
         SlashCommand::Clear { confirm } => {
@@ -1968,6 +2145,7 @@ fn run_resume_command(
                     message: Some(
                         "clear: confirmation required; rerun with /clear --confirm".to_string(),
                     ),
+                    json: None,
                 });
             }
             let backup_path = write_session_clear_backup(session, session_path)?;
@@ -1983,11 +2161,13 @@ fn run_resume_command(
                     backup_path.display(),
                     session_path.display()
                 )),
+                json: None,
             })
         }
         SlashCommand::Status => {
             let tracker = UsageTracker::from_session(session);
             let usage = tracker.cumulative_usage();
+            let context = status_context(Some(session_path))?;
             Ok(ResumeCommandOutcome {
                 session: session.clone(),
                 message: Some(format_status_report(
@@ -2000,7 +2180,19 @@ fn run_resume_command(
                         estimated_tokens: 0,
                     },
                     default_permission_mode().as_str(),
-                    &status_context(Some(session_path))?,
+                    &context,
+                )),
+                json: Some(status_json_value(
+                    "restored-session",
+                    StatusUsage {
+                        message_count: session.messages.len(),
+                        turns: tracker.turns(),
+                        latest: tracker.current_turn_usage(),
+                        cumulative: usage,
+                        estimated_tokens: 0,
+                    },
+                    default_permission_mode().as_str(),
+                    &context,
                 )),
             })
         }
@@ -2008,12 +2200,11 @@ fn run_resume_command(
             let cwd = env::current_dir()?;
             let loader = ConfigLoader::default_for(&cwd);
             let runtime_config = loader.load()?;
+            let status = resolve_sandbox_status(runtime_config.sandbox(), &cwd);
             Ok(ResumeCommandOutcome {
                 session: session.clone(),
-                message: Some(format_sandbox_report(&resolve_sandbox_status(
-                    runtime_config.sandbox(),
-                    &cwd,
-                ))),
+                message: Some(format_sandbox_report(&status)),
+                json: Some(sandbox_json_value(&status)),
             })
         }
         SlashCommand::Cost => {
@@ -2021,11 +2212,13 @@ fn run_resume_command(
             Ok(ResumeCommandOutcome {
                 session: session.clone(),
                 message: Some(format_cost_report(usage)),
+                json: None,
             })
         }
         SlashCommand::Config { section } => Ok(ResumeCommandOutcome {
             session: session.clone(),
             message: Some(render_config_report(section.as_deref())?),
+            json: None,
         }),
         SlashCommand::Mcp { action, target } => {
             let cwd = env::current_dir()?;
@@ -2038,25 +2231,33 @@ fn run_resume_command(
             Ok(ResumeCommandOutcome {
                 session: session.clone(),
                 message: Some(handle_mcp_slash_command(args.as_deref(), &cwd)?),
+                json: Some(handle_mcp_slash_command_json(args.as_deref(), &cwd)?),
             })
         }
         SlashCommand::Memory => Ok(ResumeCommandOutcome {
             session: session.clone(),
             message: Some(render_memory_report()?),
+            json: None,
         }),
-        SlashCommand::Init => Ok(ResumeCommandOutcome {
-            session: session.clone(),
-            message: Some(init_claude_md()?),
-        }),
+        SlashCommand::Init => {
+            let message = init_claude_md()?;
+            Ok(ResumeCommandOutcome {
+                session: session.clone(),
+                message: Some(message.clone()),
+                json: Some(init_json_value(&message)),
+            })
+        }
         SlashCommand::Diff => Ok(ResumeCommandOutcome {
             session: session.clone(),
             message: Some(render_diff_report_for(
                 session_path.parent().unwrap_or_else(|| Path::new(".")),
             )?),
+            json: None,
         }),
         SlashCommand::Version => Ok(ResumeCommandOutcome {
             session: session.clone(),
             message: Some(render_version_report()),
+            json: Some(version_json_value()),
         }),
         SlashCommand::Export { path } => {
             let export_path = resolve_export_path(path.as_deref(), session)?;
@@ -2068,6 +2269,7 @@ fn run_resume_command(
                     export_path.display(),
                     session.messages.len(),
                 )),
+                json: None,
             })
         }
         SlashCommand::Agents { args } => {
@@ -2075,6 +2277,7 @@ fn run_resume_command(
             Ok(ResumeCommandOutcome {
                 session: session.clone(),
                 message: Some(handle_agents_slash_command(args.as_deref(), &cwd)?),
+                json: None,
             })
         }
         SlashCommand::Skills { args } => {
@@ -2082,11 +2285,13 @@ fn run_resume_command(
             Ok(ResumeCommandOutcome {
                 session: session.clone(),
                 message: Some(handle_skills_slash_command(args.as_deref(), &cwd)?),
+                json: Some(handle_skills_slash_command_json(args.as_deref(), &cwd)?),
             })
         }
         SlashCommand::Doctor => Ok(ResumeCommandOutcome {
             session: session.clone(),
             message: Some(render_doctor_report()?.render()),
+            json: None,
         }),
         SlashCommand::Unknown(name) => Err(format_unknown_slash_command(name).into()),
         SlashCommand::Bughunter { .. }
@@ -3281,16 +3486,11 @@ impl LiveCli {
         output_format: CliOutputFormat,
     ) -> Result<(), Box<dyn std::error::Error>> {
         let cwd = env::current_dir()?;
-        let message = handle_agents_slash_command(args, &cwd)?;
         match output_format {
-            CliOutputFormat::Text => println!("{message}"),
+            CliOutputFormat::Text => println!("{}", handle_agents_slash_command(args, &cwd)?),
             CliOutputFormat::Json => println!(
                 "{}",
-                serde_json::to_string_pretty(&json!({
-                    "kind": "agents",
-                    "message": message,
-                    "args": args,
-                }))?
+                serde_json::to_string_pretty(&handle_agents_slash_command_json(args, &cwd)?)?
             ),
         }
         Ok(())
@@ -3845,54 +4045,68 @@ fn print_status_snapshot(
         ),
         CliOutputFormat::Json => println!(
             "{}",
-            serde_json::to_string_pretty(&json!({
-                "kind": "status",
-                "model": model,
-                "permission_mode": permission_mode.as_str(),
-                "usage": {
-                    "messages": usage.message_count,
-                    "turns": usage.turns,
-                    "latest_total": usage.latest.total_tokens(),
-                    "cumulative_input": usage.cumulative.input_tokens,
-                    "cumulative_output": usage.cumulative.output_tokens,
-                    "cumulative_total": usage.cumulative.total_tokens(),
-                    "estimated_tokens": usage.estimated_tokens,
-                },
-                "workspace": {
-                    "cwd": context.cwd,
-                    "project_root": context.project_root,
-                    "git_branch": context.git_branch,
-                    "git_state": context.git_summary.headline(),
-                    "changed_files": context.git_summary.changed_files,
-                    "staged_files": context.git_summary.staged_files,
-                    "unstaged_files": context.git_summary.unstaged_files,
-                    "untracked_files": context.git_summary.untracked_files,
-                    "session": context.session_path.as_ref().map_or_else(|| "live-repl".to_string(), |path| path.display().to_string()),
-                    "loaded_config_files": context.loaded_config_files,
-                    "discovered_config_files": context.discovered_config_files,
-                    "memory_file_count": context.memory_file_count,
-                },
-                "sandbox": {
-                    "enabled": context.sandbox_status.enabled,
-                    "active": context.sandbox_status.active,
-                    "supported": context.sandbox_status.supported,
-                    "in_container": context.sandbox_status.in_container,
-                    "requested_namespace": context.sandbox_status.requested.namespace_restrictions,
-                    "active_namespace": context.sandbox_status.namespace_active,
-                    "requested_network": context.sandbox_status.requested.network_isolation,
-                    "active_network": context.sandbox_status.network_active,
-                    "filesystem_mode": context.sandbox_status.filesystem_mode.as_str(),
-                    "filesystem_active": context.sandbox_status.filesystem_active,
-                    "allowed_mounts": context.sandbox_status.allowed_mounts,
-                    "markers": context.sandbox_status.container_markers,
-                    "fallback_reason": context.sandbox_status.fallback_reason,
-                }
-            }))?
+            serde_json::to_string_pretty(&status_json_value(
+                model,
+                usage,
+                permission_mode.as_str(),
+                &context,
+            ))?
         ),
     }
     Ok(())
 }
 
+fn status_json_value(
+    model: &str,
+    usage: StatusUsage,
+    permission_mode: &str,
+    context: &StatusContext,
+) -> serde_json::Value {
+    json!({
+        "kind": "status",
+        "model": model,
+        "permission_mode": permission_mode,
+        "usage": {
+            "messages": usage.message_count,
+            "turns": usage.turns,
+            "latest_total": usage.latest.total_tokens(),
+            "cumulative_input": usage.cumulative.input_tokens,
+            "cumulative_output": usage.cumulative.output_tokens,
+            "cumulative_total": usage.cumulative.total_tokens(),
+            "estimated_tokens": usage.estimated_tokens,
+        },
+        "workspace": {
+            "cwd": context.cwd,
+            "project_root": context.project_root,
+            "git_branch": context.git_branch,
+            "git_state": context.git_summary.headline(),
+            "changed_files": context.git_summary.changed_files,
+            "staged_files": context.git_summary.staged_files,
+            "unstaged_files": context.git_summary.unstaged_files,
+            "untracked_files": context.git_summary.untracked_files,
+            "session": context.session_path.as_ref().map_or_else(|| "live-repl".to_string(), |path| path.display().to_string()),
+            "loaded_config_files": context.loaded_config_files,
+            "discovered_config_files": context.discovered_config_files,
+            "memory_file_count": context.memory_file_count,
+        },
+        "sandbox": {
+            "enabled": context.sandbox_status.enabled,
+            "active": context.sandbox_status.active,
+            "supported": context.sandbox_status.supported,
+            "in_container": context.sandbox_status.in_container,
+            "requested_namespace": context.sandbox_status.requested.namespace_restrictions,
+            "active_namespace": context.sandbox_status.namespace_active,
+            "requested_network": context.sandbox_status.requested.network_isolation,
+            "active_network": context.sandbox_status.network_active,
+            "filesystem_mode": context.sandbox_status.filesystem_mode.as_str(),
+            "filesystem_active": context.sandbox_status.filesystem_active,
+            "allowed_mounts": context.sandbox_status.allowed_mounts,
+            "markers": context.sandbox_status.container_markers,
+            "fallback_reason": context.sandbox_status.fallback_reason,
+        }
+    })
+}
+
 fn status_context(
     session_path: Option<&Path>,
 ) -> Result<StatusContext, Box<dyn std::error::Error>> {
@@ -4066,27 +4280,31 @@ fn print_sandbox_status_snapshot(
         CliOutputFormat::Text => println!("{}", format_sandbox_report(&status)),
         CliOutputFormat::Json => println!(
             "{}",
-            serde_json::to_string_pretty(&json!({
-                "kind": "sandbox",
-                "enabled": status.enabled,
-                "active": status.active,
-                "supported": status.supported,
-                "in_container": status.in_container,
-                "requested_namespace": status.requested.namespace_restrictions,
-                "active_namespace": status.namespace_active,
-                "requested_network": status.requested.network_isolation,
-                "active_network": status.network_active,
-                "filesystem_mode": status.filesystem_mode.as_str(),
-                "filesystem_active": status.filesystem_active,
-                "allowed_mounts": status.allowed_mounts,
-                "markers": status.container_markers,
-                "fallback_reason": status.fallback_reason,
-            }))?
+            serde_json::to_string_pretty(&sandbox_json_value(&status))?
         ),
     }
     Ok(())
 }
 
+fn sandbox_json_value(status: &runtime::SandboxStatus) -> serde_json::Value {
+    json!({
+        "kind": "sandbox",
+        "enabled": status.enabled,
+        "active": status.active,
+        "supported": status.supported,
+        "in_container": status.in_container,
+        "requested_namespace": status.requested.namespace_restrictions,
+        "active_namespace": status.namespace_active,
+        "requested_network": status.requested.network_isolation,
+        "active_network": status.network_active,
+        "filesystem_mode": status.filesystem_mode.as_str(),
+        "filesystem_active": status.filesystem_active,
+        "allowed_mounts": status.allowed_mounts,
+        "markers": status.container_markers,
+        "fallback_reason": status.fallback_reason,
+    })
+}
+
 fn render_help_topic(topic: LocalHelpTopic) -> String {
     match topic {
         LocalHelpTopic::Status => "Status
@@ -4243,15 +4461,19 @@ fn run_init(output_format: CliOutputFormat) -> Result<(), Box<dyn std::error::Er
         CliOutputFormat::Text => println!("{message}"),
         CliOutputFormat::Json => println!(
             "{}",
-            serde_json::to_string_pretty(&json!({
-                "kind": "init",
-                "message": message,
-            }))?
+            serde_json::to_string_pretty(&init_json_value(&message))?
         ),
     }
     Ok(())
 }
 
+fn init_json_value(message: &str) -> serde_json::Value {
+    json!({
+        "kind": "init",
+        "message": message,
+    })
+}
+
 fn normalize_permission_mode(mode: &str) -> Option<&'static str> {
     match mode.trim() {
         "read-only" => Some("read-only"),
@@ -5230,6 +5452,7 @@ impl runtime::PermissionPrompter for CliPermissionPrompter {
 struct AnthropicRuntimeClient {
     runtime: tokio::runtime::Runtime,
     client: AnthropicClient,
+    session_id: String,
     model: String,
     enable_tools: bool,
     emit_output: bool,
@@ -5253,6 +5476,7 @@ 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,
@@ -5292,11 +5516,13 @@ 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 {
@@ -5310,11 +5536,9 @@ 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 {
@@ -5409,7 +5633,9 @@ 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)
@@ -5417,6 +5643,23 @@ 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
@@ -6415,18 +6658,19 @@ 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,
     };
@@ -6466,12 +6710,59 @@ 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 {
+        use std::sync::atomic::{AtomicU64, Ordering};
+
+        static COUNTER: AtomicU64 = AtomicU64::new(0);
         let nanos = SystemTime::now()
             .duration_since(UNIX_EPOCH)
             .expect("time should be after epoch")
             .as_nanos();
-        std::env::temp_dir().join(format!("rusty-claude-cli-{nanos}"))
+        let unique = COUNTER.fetch_add(1, Ordering::Relaxed);
+        std::env::temp_dir().join(format!("rusty-claude-cli-{nanos}-{unique}"))
     }
 
     fn git(args: &[&str], cwd: &Path) {

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

@@ -50,8 +50,34 @@ fn inventory_commands_emit_structured_json_when_requested() {
     let root = unique_temp_dir("inventory-json");
     fs::create_dir_all(&root).expect("temp dir should exist");
 
-    let agents = assert_json_command(&root, &["--output-format", "json", "agents"]);
+    let isolated_home = root.join("home");
+    let isolated_config = root.join("config-home");
+    let isolated_codex = root.join("codex-home");
+    fs::create_dir_all(&isolated_home).expect("isolated home should exist");
+
+    let agents = assert_json_command_with_env(
+        &root,
+        &["--output-format", "json", "agents"],
+        &[
+            ("HOME", isolated_home.to_str().expect("utf8 home")),
+            (
+                "CLAW_CONFIG_HOME",
+                isolated_config.to_str().expect("utf8 config home"),
+            ),
+            (
+                "CODEX_HOME",
+                isolated_codex.to_str().expect("utf8 codex home"),
+            ),
+        ],
+    );
     assert_eq!(agents["kind"], "agents");
+    assert_eq!(agents["action"], "list");
+    assert_eq!(agents["count"], 0);
+    assert_eq!(agents["summary"]["active"], 0);
+    assert!(agents["agents"]
+        .as_array()
+        .expect("agents array")
+        .is_empty());
 
     let mcp = assert_json_command(&root, &["--output-format", "json", "mcp"]);
     assert_eq!(mcp["kind"], "mcp");
@@ -62,6 +88,68 @@ fn inventory_commands_emit_structured_json_when_requested() {
     assert_eq!(skills["action"], "list");
 }
 
+#[test]
+fn agents_command_emits_structured_agent_entries_when_requested() {
+    let root = unique_temp_dir("agents-json-populated");
+    let workspace = root.join("workspace");
+    let project_agents = workspace.join(".codex").join("agents");
+    let home = root.join("home");
+    let user_agents = home.join(".codex").join("agents");
+    let isolated_config = root.join("config-home");
+    let isolated_codex = root.join("codex-home");
+    fs::create_dir_all(&workspace).expect("workspace should exist");
+    write_agent(
+        &project_agents,
+        "planner",
+        "Project planner",
+        "gpt-5.4",
+        "medium",
+    );
+    write_agent(
+        &project_agents,
+        "verifier",
+        "Verification agent",
+        "gpt-5.4-mini",
+        "high",
+    );
+    write_agent(
+        &user_agents,
+        "planner",
+        "User planner",
+        "gpt-5.4-mini",
+        "high",
+    );
+
+    let parsed = assert_json_command_with_env(
+        &workspace,
+        &["--output-format", "json", "agents"],
+        &[
+            ("HOME", home.to_str().expect("utf8 home")),
+            (
+                "CLAW_CONFIG_HOME",
+                isolated_config.to_str().expect("utf8 config home"),
+            ),
+            (
+                "CODEX_HOME",
+                isolated_codex.to_str().expect("utf8 codex home"),
+            ),
+        ],
+    );
+
+    assert_eq!(parsed["kind"], "agents");
+    assert_eq!(parsed["action"], "list");
+    assert_eq!(parsed["count"], 3);
+    assert_eq!(parsed["summary"]["active"], 2);
+    assert_eq!(parsed["summary"]["shadowed"], 1);
+    assert_eq!(parsed["agents"][0]["name"], "planner");
+    assert_eq!(parsed["agents"][0]["source"]["id"], "project_claw");
+    assert_eq!(parsed["agents"][0]["active"], true);
+    assert_eq!(parsed["agents"][1]["name"], "verifier");
+    assert_eq!(parsed["agents"][2]["name"], "planner");
+    assert_eq!(parsed["agents"][2]["active"], false);
+    assert_eq!(parsed["agents"][2]["shadowed_by"]["id"], "project_claw");
+}
+
 #[test]
 fn bootstrap_and_system_prompt_emit_json_when_requested() {
     let root = unique_temp_dir("bootstrap-system-prompt-json");
@@ -112,6 +200,41 @@ fn doctor_and_resume_status_emit_json_when_requested() {
     let doctor = assert_json_command(&root, &["--output-format", "json", "doctor"]);
     assert_eq!(doctor["kind"], "doctor");
     assert!(doctor["message"].is_string());
+    let summary = doctor["summary"].as_object().expect("doctor summary");
+    assert!(summary["ok"].as_u64().is_some());
+    assert!(summary["warnings"].as_u64().is_some());
+    assert!(summary["failures"].as_u64().is_some());
+
+    let checks = doctor["checks"].as_array().expect("doctor checks");
+    assert_eq!(checks.len(), 5);
+    let check_names = checks
+        .iter()
+        .map(|check| {
+            assert!(check["status"].as_str().is_some());
+            assert!(check["summary"].as_str().is_some());
+            assert!(check["details"].is_array());
+            check["name"].as_str().expect("doctor check name")
+        })
+        .collect::<Vec<_>>();
+    assert_eq!(
+        check_names,
+        vec!["auth", "config", "workspace", "sandbox", "system"]
+    );
+
+    let workspace = checks
+        .iter()
+        .find(|check| check["name"] == "workspace")
+        .expect("workspace check");
+    assert!(workspace["cwd"].as_str().is_some());
+    assert!(workspace["in_git_repo"].is_boolean());
+
+    let sandbox = checks
+        .iter()
+        .find(|check| check["name"] == "sandbox")
+        .expect("sandbox check");
+    assert!(sandbox["filesystem_mode"].as_str().is_some());
+    assert!(sandbox["enabled"].is_boolean());
+    assert!(sandbox["fallback_reason"].is_null() || sandbox["fallback_reason"].is_string());
 
     let session_path = root.join("session.jsonl");
     fs::write(
@@ -130,7 +253,108 @@ fn doctor_and_resume_status_emit_json_when_requested() {
         ],
     );
     assert_eq!(resumed["kind"], "status");
-    assert_eq!(resumed["messages"], 1);
+    assert_eq!(resumed["model"], "restored-session");
+    assert_eq!(resumed["usage"]["messages"], 1);
+    assert!(resumed["workspace"]["cwd"].as_str().is_some());
+    assert!(resumed["sandbox"]["filesystem_mode"].as_str().is_some());
+}
+
+#[test]
+fn resumed_inventory_commands_emit_structured_json_when_requested() {
+    let root = unique_temp_dir("resume-inventory-json");
+    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");
+
+    let session_path = root.join("session.jsonl");
+    fs::write(
+        &session_path,
+        "{\"type\":\"session_meta\",\"version\":3,\"session_id\":\"resume-inventory-json\",\"created_at_ms\":0,\"updated_at_ms\":0}\n{\"type\":\"message\",\"message\":{\"role\":\"user\",\"blocks\":[{\"type\":\"text\",\"text\":\"inventory\"}]}}\n",
+    )
+    .expect("session should write");
+
+    let mcp = assert_json_command_with_env(
+        &root,
+        &[
+            "--output-format",
+            "json",
+            "--resume",
+            session_path.to_str().expect("utf8 session path"),
+            "/mcp",
+        ],
+        &[
+            (
+                "CLAW_CONFIG_HOME",
+                config_home.to_str().expect("utf8 config home"),
+            ),
+            ("HOME", home.to_str().expect("utf8 home")),
+        ],
+    );
+    assert_eq!(mcp["kind"], "mcp");
+    assert_eq!(mcp["action"], "list");
+    assert!(mcp["servers"].is_array());
+
+    let skills = assert_json_command_with_env(
+        &root,
+        &[
+            "--output-format",
+            "json",
+            "--resume",
+            session_path.to_str().expect("utf8 session path"),
+            "/skills",
+        ],
+        &[
+            (
+                "CLAW_CONFIG_HOME",
+                config_home.to_str().expect("utf8 config home"),
+            ),
+            ("HOME", home.to_str().expect("utf8 home")),
+        ],
+    );
+    assert_eq!(skills["kind"], "skills");
+    assert_eq!(skills["action"], "list");
+    assert!(skills["summary"]["total"].is_number());
+    assert!(skills["skills"].is_array());
+}
+
+#[test]
+fn resumed_version_and_init_emit_structured_json_when_requested() {
+    let root = unique_temp_dir("resume-version-init-json");
+    fs::create_dir_all(&root).expect("temp dir should exist");
+
+    let session_path = root.join("session.jsonl");
+    fs::write(
+        &session_path,
+        "{\"type\":\"session_meta\",\"version\":3,\"session_id\":\"resume-version-init-json\",\"created_at_ms\":0,\"updated_at_ms\":0}\n",
+    )
+    .expect("session should write");
+
+    let version = assert_json_command(
+        &root,
+        &[
+            "--output-format",
+            "json",
+            "--resume",
+            session_path.to_str().expect("utf8 session path"),
+            "/version",
+        ],
+    );
+    assert_eq!(version["kind"], "version");
+    assert_eq!(version["version"], env!("CARGO_PKG_VERSION"));
+
+    let init = assert_json_command(
+        &root,
+        &[
+            "--output-format",
+            "json",
+            "--resume",
+            session_path.to_str().expect("utf8 session path"),
+            "/init",
+        ],
+    );
+    assert_eq!(init["kind"], "init");
+    assert!(root.join("CLAUDE.md").exists());
 }
 
 fn assert_json_command(current_dir: &Path, args: &[&str]) -> Value {
@@ -180,6 +404,17 @@ fn write_upstream_fixture(root: &Path) -> PathBuf {
     upstream
 }
 
+fn write_agent(root: &Path, name: &str, description: &str, model: &str, reasoning: &str) {
+    fs::create_dir_all(root).expect("agent root should exist");
+    fs::write(
+        root.join(format!("{name}.toml")),
+        format!(
+            "name = \"{name}\"\ndescription = \"{description}\"\nmodel = \"{model}\"\nmodel_reasoning_effort = \"{reasoning}\"\n"
+        ),
+    )
+    .expect("agent fixture should write");
+}
+
 fn unique_temp_dir(label: &str) -> PathBuf {
     let millis = SystemTime::now()
         .duration_since(UNIX_EPOCH)

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

@@ -261,11 +261,61 @@ fn resumed_status_command_emits_structured_json_when_requested() {
     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["model"], "restored-session");
+    assert_eq!(parsed["permission_mode"], "danger-full-access");
+    assert_eq!(parsed["usage"]["messages"], 1);
+    assert!(parsed["usage"]["turns"].is_number());
+    assert!(parsed["workspace"]["cwd"].as_str().is_some());
     assert_eq!(
         parsed["workspace"]["session"],
         session_path.to_str().expect("utf8 path")
     );
+    assert!(parsed["workspace"]["changed_files"].is_number());
+    assert_eq!(parsed["workspace"]["loaded_config_files"].as_u64(), Some(0));
+    assert!(parsed["sandbox"]["filesystem_mode"].as_str().is_some());
+}
+
+#[test]
+fn resumed_sandbox_command_emits_structured_json_when_requested() {
+    // given
+    let temp_dir = unique_temp_dir("resume-sandbox-json");
+    fs::create_dir_all(&temp_dir).expect("temp dir should exist");
+    let session_path = temp_dir.join("session.jsonl");
+
+    Session::new()
+        .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"),
+            "/sandbox",
+        ],
+    );
+
+    // 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 sandbox output should be json");
+    assert_eq!(parsed["kind"], "sandbox");
+    assert!(parsed["enabled"].is_boolean());
+    assert!(parsed["active"].is_boolean());
+    assert!(parsed["supported"].is_boolean());
+    assert!(parsed["filesystem_mode"].as_str().is_some());
+    assert!(parsed["allowed_mounts"].is_array());
+    assert!(parsed["markers"].is_array());
 }
 
 fn run_claw(current_dir: &Path, args: &[&str]) -> Output {