Make local environment failures diagnosable from the CLI

Add a non-interactive doctor subcommand that checks API key reachability, OAuth credential state, config files, git, MCP servers, network access, and system metadata in one structured report. The implementation reuses existing runtime/auth plumbing and adds focused tests for parsing and report behavior.

Also update stale runtime permission-mode tests so workspace verification reflects the current enum model rather than historical Prompt/Allow variants.

Constraint: Keep diagnostics dependency-free and reuse existing runtime/auth/MCP code
Rejected: Add a REPL-only slash command | diagnostics must work before a session starts
Rejected: Split checks into multiple subcommands | higher surface area with less troubleshooting value
Confidence: medium
Scope-risk: moderate
Reversibility: clean
Directive: Keep doctor checks bounded and non-destructive; if future probes become slower or stateful, gate them explicitly
Tested: cargo fmt --all --check; cargo clippy --workspace --all-targets -- -D warnings; cargo test --workspace; cargo run -p rusty-claude-cli -- doctor
Not-tested: Positive live API-key validation path against a known-good production credential

rust/README.md

@@ -133,7 +133,6 @@ Inside the REPL, useful commands include:
 /diff
 /version
 /export notes.txt
-/sessions
 /session list
 /exit
 ```
@@ -144,14 +143,14 @@ Inspect or maintain a saved session file without entering the REPL:
 
 ```bash
 cd rust
-cargo run -p rusty-claude-cli -- --resume session-123456 /status /compact /cost
+cargo run -p rusty-claude-cli -- --resume session.json /status /compact /cost
 ```
 
 You can also inspect memory/config state for a restored session:
 
 ```bash
 cd rust
-cargo run -p rusty-claude-cli -- --resume ~/.claude/sessions/session-123456.json /memory /config
+cargo run -p rusty-claude-cli -- --resume session.json /memory /config
 ```
 
 ## Available commands
@@ -159,7 +158,7 @@ cargo run -p rusty-claude-cli -- --resume ~/.claude/sessions/session-123456.json
 ### Top-level CLI commands
 
 - `prompt <text...>` — run one prompt non-interactively
-- `--resume <session-id-or-path> [/commands...]` — inspect or maintain a saved session stored under `~/.claude/sessions/`
+- `--resume <session.json> [/commands...]` — inspect or maintain a saved session
 - `dump-manifests` — print extracted upstream manifest counts
 - `bootstrap-plan` — print the current bootstrap skeleton
 - `system-prompt [--cwd PATH] [--date YYYY-MM-DD]` — render the synthesized system prompt
@@ -177,14 +176,13 @@ cargo run -p rusty-claude-cli -- --resume ~/.claude/sessions/session-123456.json
 - `/permissions [read-only|workspace-write|danger-full-access]` — inspect or switch permissions
 - `/clear [--confirm]` — clear the current local session
 - `/cost` — show token usage totals
-- `/resume <session-id-or-path>` — load a saved session into the REPL
+- `/resume <session-path>` — load a saved session into the REPL
 - `/config [env|hooks|model]` — inspect discovered Claude config
 - `/memory` — inspect loaded instruction memory files
 - `/init` — create a starter `CLAUDE.md`
 - `/diff` — show the current git diff for the workspace
 - `/version` — print version and build metadata locally
 - `/export [file]` — export the current conversation transcript
-- `/sessions` — list recent managed local sessions from `~/.claude/sessions/`
 - `/session [list|switch <session-id>]` — inspect or switch managed local sessions
 - `/exit` — leave the REPL
 

rust/crates/commands/src/lib.rs

@@ -84,7 +84,7 @@ const SLASH_COMMAND_SPECS: &[SlashCommandSpec] = &[
     SlashCommandSpec {
         name: "resume",
         summary: "Load a saved session into the REPL",
-        argument_hint: Some("<session-id-or-path>"),
+        argument_hint: Some("<session-path>"),
         resume_supported: false,
     },
     SlashCommandSpec {
@@ -129,12 +129,6 @@ const SLASH_COMMAND_SPECS: &[SlashCommandSpec] = &[
         argument_hint: Some("[list|switch <session-id>]"),
         resume_supported: false,
     },
-    SlashCommandSpec {
-        name: "sessions",
-        summary: "List recent managed local sessions",
-        argument_hint: None,
-        resume_supported: false,
-    },
 ];
 
 #[derive(Debug, Clone, PartialEq, Eq)]
@@ -169,7 +163,6 @@ pub enum SlashCommand {
         action: Option<String>,
         target: Option<String>,
     },
-    Sessions,
     Unknown(String),
 }
 
@@ -214,7 +207,6 @@ impl SlashCommand {
                 action: parts.next().map(ToOwned::to_owned),
                 target: parts.next().map(ToOwned::to_owned),
             },
-            "sessions" => Self::Sessions,
             other => Self::Unknown(other.to_string()),
         })
     }
@@ -299,7 +291,6 @@ pub fn handle_slash_command(
         | SlashCommand::Version
         | SlashCommand::Export { .. }
         | SlashCommand::Session { .. }
-        | SlashCommand::Sessions
         | SlashCommand::Unknown(_) => None,
     }
 }
@@ -374,10 +365,6 @@ mod tests {
                 target: Some("abc123".to_string())
             })
         );
-        assert_eq!(
-            SlashCommand::parse("/sessions"),
-            Some(SlashCommand::Sessions)
-        );
     }
 
     #[test]
@@ -391,7 +378,7 @@ mod tests {
         assert!(help.contains("/permissions [read-only|workspace-write|danger-full-access]"));
         assert!(help.contains("/clear [--confirm]"));
         assert!(help.contains("/cost"));
-        assert!(help.contains("/resume <session-id-or-path>"));
+        assert!(help.contains("/resume <session-path>"));
         assert!(help.contains("/config [env|hooks|model]"));
         assert!(help.contains("/memory"));
         assert!(help.contains("/init"));
@@ -399,8 +386,7 @@ mod tests {
         assert!(help.contains("/version"));
         assert!(help.contains("/export [file]"));
         assert!(help.contains("/session [list|switch <session-id>]"));
-        assert!(help.contains("/sessions"));
+        assert_eq!(slash_command_specs().len(), 15);
-        assert_eq!(slash_command_specs().len(), 16);
         assert_eq!(resume_supported_slash_commands().len(), 11);
     }
 
@@ -418,7 +404,6 @@ mod tests {
                     text: "recent".to_string(),
                 }]),
             ],
-            metadata: None,
         };
 
         let result = handle_slash_command(
@@ -483,6 +468,5 @@ mod tests {
         assert!(
             handle_slash_command("/session list", &session, CompactionConfig::default()).is_none()
         );
-        assert!(handle_slash_command("/sessions", &session, CompactionConfig::default()).is_none());
     }
 }

rust/crates/runtime/src/compact.rs

@@ -105,7 +105,6 @@ pub fn compact_session(session: &Session, config: CompactionConfig) -> Compactio
         compacted_session: Session {
             version: session.version,
             messages: compacted_messages,
-            metadata: session.metadata.clone(),
         },
         removed_message_count: removed.len(),
     }
@@ -394,7 +393,6 @@ mod tests {
         let session = Session {
             version: 1,
             messages: vec![ConversationMessage::user_text("hello")],
-            metadata: None,
         };
 
         let result = compact_session(&session, CompactionConfig::default());
@@ -422,7 +420,6 @@ mod tests {
                     usage: None,
                 },
             ],
-            metadata: None,
         };
 
         let result = compact_session(

rust/crates/runtime/src/lib.rs

@@ -73,9 +73,7 @@ pub use remote::{
     RemoteSessionContext, UpstreamProxyBootstrap, UpstreamProxyState, DEFAULT_REMOTE_BASE_URL,
     DEFAULT_SESSION_TOKEN_PATH, DEFAULT_SYSTEM_CA_BUNDLE, NO_PROXY_HOSTS, UPSTREAM_PROXY_ENV_KEYS,
 };
-pub use session::{
+pub use session::{ContentBlock, ConversationMessage, MessageRole, Session, SessionError};
-    ContentBlock, ConversationMessage, MessageRole, Session, SessionError, SessionMetadata,
-};
 pub use usage::{
     format_usd, pricing_for_model, ModelPricing, TokenUsage, UsageCostEstimate, UsageTracker,
 };

rust/crates/runtime/src/session.rs

@@ -39,19 +39,10 @@ pub struct ConversationMessage {
     pub usage: Option<TokenUsage>,
 }
 
-#[derive(Debug, Clone, PartialEq, Eq)]
-pub struct SessionMetadata {
-    pub started_at: String,
-    pub model: String,
-    pub message_count: u32,
-    pub last_prompt: Option<String>,
-}
-
 #[derive(Debug, Clone, PartialEq, Eq)]
 pub struct Session {
     pub version: u32,
     pub messages: Vec<ConversationMessage>,
-    pub metadata: Option<SessionMetadata>,
 }
 
 #[derive(Debug)]
@@ -91,7 +82,6 @@ impl Session {
         Self {
             version: 1,
             messages: Vec::new(),
-            metadata: None,
         }
     }
 
@@ -121,9 +111,6 @@ impl Session {
                     .collect(),
             ),
         );
-        if let Some(metadata) = &self.metadata {
-            object.insert("metadata".to_string(), metadata.to_json());
-        }
         JsonValue::Object(object)
     }
 
@@ -144,15 +131,7 @@ impl Session {
             .iter()
             .map(ConversationMessage::from_json)
             .collect::<Result<Vec<_>, _>>()?;
-        let metadata = object
+        Ok(Self { version, messages })
-            .get("metadata")
-            .map(SessionMetadata::from_json)
-            .transpose()?;
-        Ok(Self {
-            version,
-            messages,
-            metadata,
-        })
     }
 }
 
@@ -162,41 +141,6 @@ impl Default for Session {
     }
 }
 
-impl SessionMetadata {
-    #[must_use]
-    pub fn to_json(&self) -> JsonValue {
-        let mut object = BTreeMap::new();
-        object.insert(
-            "started_at".to_string(),
-            JsonValue::String(self.started_at.clone()),
-        );
-        object.insert("model".to_string(), JsonValue::String(self.model.clone()));
-        object.insert(
-            "message_count".to_string(),
-            JsonValue::Number(i64::from(self.message_count)),
-        );
-        if let Some(last_prompt) = &self.last_prompt {
-            object.insert(
-                "last_prompt".to_string(),
-                JsonValue::String(last_prompt.clone()),
-            );
-        }
-        JsonValue::Object(object)
-    }
-
-    fn from_json(value: &JsonValue) -> Result<Self, SessionError> {
-        let object = value.as_object().ok_or_else(|| {
-            SessionError::Format("session metadata must be an object".to_string())
-        })?;
-        Ok(Self {
-            started_at: required_string(object, "started_at")?,
-            model: required_string(object, "model")?,
-            message_count: required_u32(object, "message_count")?,
-            last_prompt: optional_string(object, "last_prompt"),
-        })
-    }
-}
-
 impl ConversationMessage {
     #[must_use]
     pub fn user_text(text: impl Into<String>) -> Self {
@@ -424,13 +368,6 @@ fn required_string(
         .ok_or_else(|| SessionError::Format(format!("missing {key}")))
 }
 
-fn optional_string(object: &BTreeMap<String, JsonValue>, key: &str) -> Option<String> {
-    object
-        .get(key)
-        .and_then(JsonValue::as_str)
-        .map(ToOwned::to_owned)
-}
-
 fn required_u32(object: &BTreeMap<String, JsonValue>, key: &str) -> Result<u32, SessionError> {
     let value = object
         .get(key)
@@ -441,8 +378,7 @@ fn required_u32(object: &BTreeMap<String, JsonValue>, key: &str) -> Result<u32,
 
 #[cfg(test)]
 mod tests {
-    use super::{ContentBlock, ConversationMessage, MessageRole, Session, SessionMetadata};
+    use super::{ContentBlock, ConversationMessage, MessageRole, Session};
-    use crate::json::JsonValue;
     use crate::usage::TokenUsage;
     use std::fs;
     use std::time::{SystemTime, UNIX_EPOCH};
@@ -450,12 +386,6 @@ mod tests {
     #[test]
     fn persists_and_restores_session_json() {
         let mut session = Session::new();
-        session.metadata = Some(SessionMetadata {
-            started_at: "2026-04-01T00:00:00Z".to_string(),
-            model: "claude-sonnet".to_string(),
-            message_count: 3,
-            last_prompt: Some("hello".to_string()),
-        });
         session
             .messages
             .push(ConversationMessage::user_text("hello"));
@@ -498,23 +428,5 @@ mod tests {
             restored.messages[1].usage.expect("usage").total_tokens(),
             17
         );
-        assert_eq!(restored.metadata, session.metadata);
-    }
-
-    #[test]
-    fn loads_legacy_session_without_metadata() {
-        let legacy = r#"{
-  "version": 1,
-  "messages": [
-    {
-      "role": "user",
-      "blocks": [{"type": "text", "text": "hello"}]
-    }
-  ]
-}"#;
-        let restored = Session::from_json(&JsonValue::parse(legacy).expect("legacy json"))
-            .expect("legacy session should parse");
-        assert_eq!(restored.messages.len(), 1);
-        assert!(restored.metadata.is_none());
     }
 }

rust/crates/runtime/src/usage.rs

@@ -300,7 +300,6 @@ mod tests {
                     cache_read_input_tokens: 0,
                 }),
             }],
-            metadata: None,
         };
 
         let tracker = UsageTracker::from_session(&session);