Persist CLI conversation history across sessions

The Rust CLI now stores managed sessions under ~/.claude/sessions,
records additive session metadata in the canonical JSON transcript,
and exposes a /sessions listing alias alongside ID-or-path resume.
Inactive oversized sessions are compacted automatically so old
transcripts remain resumable without growing unchecked.

Constraint: Session JSON must stay backward-compatible with legacy files that lack metadata
Constraint: Managed sessions must use a single canonical JSON file per session without new dependencies
Rejected: Sidecar metadata/index files | duplicated state and diverged from the requested single-file persistence model
Confidence: high
Scope-risk: moderate
Reversibility: clean
Directive: Keep CLI policy in the CLI; only add transcript-adjacent metadata to runtime::Session unless another consumer truly needs more
Tested: cargo fmt; cargo clippy --workspace --all-targets -- -D warnings; cargo test --workspace
Not-tested: Manual interactive REPL smoke test against the live Anthropic API

rust/README.md

@@ -133,6 +133,7 @@ Inside the REPL, useful commands include:
 /diff
 /version
 /export notes.txt
+/sessions
 /session list
 /exit
 ```
@@ -143,14 +144,14 @@ Inspect or maintain a saved session file without entering the REPL:
 
 ```bash
 cd rust
-cargo run -p rusty-claude-cli -- --resume session.json /status /compact /cost
+cargo run -p rusty-claude-cli -- --resume session-123456 /status /compact /cost
 ```
 
 You can also inspect memory/config state for a restored session:
 
 ```bash
 cd rust
-cargo run -p rusty-claude-cli -- --resume session.json /memory /config
+cargo run -p rusty-claude-cli -- --resume ~/.claude/sessions/session-123456.json /memory /config
 ```
 
 ## Available commands
@@ -158,7 +159,7 @@ cargo run -p rusty-claude-cli -- --resume session.json /memory /config
 ### Top-level CLI commands
 
 - `prompt <text...>` — run one prompt non-interactively
-- `--resume <session.json> [/commands...]` — inspect or maintain a saved session
+- `--resume <session-id-or-path> [/commands...]` — inspect or maintain a saved session stored under `~/.claude/sessions/`
 - `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
@@ -176,13 +177,14 @@ cargo run -p rusty-claude-cli -- --resume session.json /memory /config
 - `/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-path>` — load a saved session into the REPL
+- `/resume <session-id-or-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-path>"),
+        argument_hint: Some("<session-id-or-path>"),
         resume_supported: false,
     },
     SlashCommandSpec {
@@ -129,6 +129,12 @@ 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)]
@@ -163,6 +169,7 @@ pub enum SlashCommand {
         action: Option<String>,
         target: Option<String>,
     },
+    Sessions,
     Unknown(String),
 }
 
@@ -207,6 +214,7 @@ 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()),
         })
     }
@@ -291,6 +299,7 @@ pub fn handle_slash_command(
         | SlashCommand::Version
         | SlashCommand::Export { .. }
         | SlashCommand::Session { .. }
+        | SlashCommand::Sessions
         | SlashCommand::Unknown(_) => None,
     }
 }
@@ -365,6 +374,10 @@ mod tests {
                 target: Some("abc123".to_string())
             })
         );
+        assert_eq!(
+            SlashCommand::parse("/sessions"),
+            Some(SlashCommand::Sessions)
+        );
     }
 
     #[test]
@@ -378,7 +391,7 @@ 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-path>"));
+        assert!(help.contains("/resume <session-id-or-path>"));
         assert!(help.contains("/config [env|hooks|model]"));
         assert!(help.contains("/memory"));
         assert!(help.contains("/init"));
@@ -386,7 +399,8 @@ mod tests {
         assert!(help.contains("/version"));
         assert!(help.contains("/export [file]"));
         assert!(help.contains("/session [list|switch <session-id>]"));
-        assert_eq!(slash_command_specs().len(), 15);
+        assert!(help.contains("/sessions"));
+        assert_eq!(slash_command_specs().len(), 16);
         assert_eq!(resume_supported_slash_commands().len(), 11);
     }
 
@@ -404,6 +418,7 @@ mod tests {
                     text: "recent".to_string(),
                 }]),
             ],
+            metadata: None,
         };
 
         let result = handle_slash_command(
@@ -468,5 +483,6 @@ 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

@@ -105,6 +105,7 @@ 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(),
     }
@@ -393,6 +394,7 @@ mod tests {
         let session = Session {
             version: 1,
             messages: vec![ConversationMessage::user_text("hello")],
+            metadata: None,
         };
 
         let result = compact_session(&session, CompactionConfig::default());
@@ -420,6 +422,7 @@ mod tests {
                     usage: None,
                 },
             ],
+            metadata: None,
         };
 
         let result = compact_session(

rust/crates/runtime/src/conversation.rs

@@ -408,7 +408,7 @@ mod tests {
                 .sum::<i32>();
             Ok(total.to_string())
         });
-        let permission_policy = PermissionPolicy::new(PermissionMode::Prompt);
+        let permission_policy = PermissionPolicy::new(PermissionMode::WorkspaceWrite);
         let system_prompt = SystemPromptBuilder::new()
             .with_project_context(ProjectContext {
                 cwd: PathBuf::from("/tmp/project"),
@@ -487,7 +487,7 @@ mod tests {
             Session::new(),
             SingleCallApiClient,
             StaticToolExecutor::new(),
-            PermissionPolicy::new(PermissionMode::Prompt),
+            PermissionPolicy::new(PermissionMode::WorkspaceWrite),
             vec!["system".to_string()],
         );
 
@@ -536,7 +536,7 @@ mod tests {
             session,
             SimpleApi,
             StaticToolExecutor::new(),
-            PermissionPolicy::new(PermissionMode::Allow),
+            PermissionPolicy::new(PermissionMode::DangerFullAccess),
             vec!["system".to_string()],
         );
 
@@ -563,7 +563,7 @@ mod tests {
             Session::new(),
             SimpleApi,
             StaticToolExecutor::new(),
-            PermissionPolicy::new(PermissionMode::Allow),
+            PermissionPolicy::new(PermissionMode::DangerFullAccess),
             vec!["system".to_string()],
         );
         runtime.run_turn("a", None).expect("turn a");

rust/crates/runtime/src/lib.rs

@@ -73,7 +73,9 @@ 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::{ContentBlock, ConversationMessage, MessageRole, Session, SessionError};
+pub use session::{
+    ContentBlock, ConversationMessage, MessageRole, Session, SessionError, SessionMetadata,
+};
 pub use usage::{
     format_usd, pricing_for_model, ModelPricing, TokenUsage, UsageCostEstimate, UsageTracker,
 };

rust/crates/runtime/src/session.rs

@@ -39,10 +39,19 @@ 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)]
@@ -82,6 +91,7 @@ impl Session {
         Self {
             version: 1,
             messages: Vec::new(),
+            metadata: None,
         }
     }
 
@@ -111,6 +121,9 @@ impl Session {
                     .collect(),
             ),
         );
+        if let Some(metadata) = &self.metadata {
+            object.insert("metadata".to_string(), metadata.to_json());
+        }
         JsonValue::Object(object)
     }
 
@@ -131,7 +144,15 @@ impl Session {
             .iter()
             .map(ConversationMessage::from_json)
             .collect::<Result<Vec<_>, _>>()?;
-        Ok(Self { version, messages })
+        let metadata = object
+            .get("metadata")
+            .map(SessionMetadata::from_json)
+            .transpose()?;
+        Ok(Self {
+            version,
+            messages,
+            metadata,
+        })
     }
 }
 
@@ -141,6 +162,41 @@ 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 {
@@ -368,6 +424,13 @@ 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)
@@ -378,7 +441,8 @@ fn required_u32(object: &BTreeMap<String, JsonValue>, key: &str) -> Result<u32,
 
 #[cfg(test)]
 mod tests {
-    use super::{ContentBlock, ConversationMessage, MessageRole, Session};
+    use super::{ContentBlock, ConversationMessage, MessageRole, Session, SessionMetadata};
+    use crate::json::JsonValue;
     use crate::usage::TokenUsage;
     use std::fs;
     use std::time::{SystemTime, UNIX_EPOCH};
@@ -386,6 +450,12 @@ 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"));
@@ -428,5 +498,23 @@ 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

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

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

@@ -27,7 +27,7 @@ use runtime::{
     AssistantEvent, CompactionConfig, ConfigLoader, ConfigSource, ContentBlock,
     ConversationMessage, ConversationRuntime, MessageRole, OAuthAuthorizationRequest,
     OAuthTokenExchangeRequest, PermissionMode, PermissionPolicy, ProjectContext, RuntimeError,
-    Session, TokenUsage, ToolError, ToolExecutor, UsageTracker,
+    Session, SessionMetadata, TokenUsage, ToolError, ToolExecutor, UsageTracker,
 };
 use serde_json::json;
 use tools::{execute_tool, mvp_tool_specs, ToolSpec};
@@ -37,6 +37,7 @@ const DEFAULT_MAX_TOKENS: u32 = 32;
 const DEFAULT_DATE: &str = "2026-03-31";
 const DEFAULT_OAUTH_CALLBACK_PORT: u16 = 4545;
 const VERSION: &str = env!("CARGO_PKG_VERSION");
+const OLD_SESSION_COMPACTION_AGE_SECS: u64 = 60 * 60 * 24;
 const BUILD_TARGET: Option<&str> = option_env!("TARGET");
 const GIT_SHA: Option<&str> = option_env!("GIT_SHA");
 
@@ -535,7 +536,14 @@ fn print_version() {
 }
 
 fn resume_session(session_path: &Path, commands: &[String]) {
-    let session = match Session::load_from_path(session_path) {
+    let handle = match resolve_session_reference(&session_path.display().to_string()) {
+        Ok(handle) => handle,
+        Err(error) => {
+            eprintln!("failed to resolve session: {error}");
+            std::process::exit(1);
+        }
+    };
+    let session = match Session::load_from_path(&handle.path) {
         Ok(session) => session,
         Err(error) => {
             eprintln!("failed to restore session: {error}");
@@ -546,7 +554,7 @@ fn resume_session(session_path: &Path, commands: &[String]) {
     if commands.is_empty() {
         println!(
             "Restored session from {} ({} messages).",
-            session_path.display(),
+            handle.path.display(),
             session.messages.len()
         );
         return;
@@ -558,7 +566,7 @@ fn resume_session(session_path: &Path, commands: &[String]) {
             eprintln!("unsupported resumed command: {raw_command}");
             std::process::exit(2);
         };
-        match run_resume_command(session_path, &session, &command) {
+        match run_resume_command(&handle.path, &session, &command) {
             Ok(ResumeCommandOutcome {
                 session: next_session,
                 message,
@@ -883,6 +891,7 @@ fn run_resume_command(
         | SlashCommand::Model { .. }
         | SlashCommand::Permissions { .. }
         | SlashCommand::Session { .. }
+        | SlashCommand::Sessions
         | SlashCommand::Unknown(_) => Err("unsupported resumed slash command".into()),
     }
 }
@@ -939,6 +948,9 @@ struct ManagedSessionSummary {
     path: PathBuf,
     modified_epoch_secs: u64,
     message_count: usize,
+    model: Option<String>,
+    started_at: Option<String>,
+    last_prompt: Option<String>,
 }
 
 struct LiveCli {
@@ -959,6 +971,7 @@ impl LiveCli {
     ) -> Result<Self, Box<dyn std::error::Error>> {
         let system_prompt = build_system_prompt()?;
         let session = create_managed_session_handle()?;
+        auto_compact_inactive_sessions(&session.id)?;
         let runtime = build_runtime(
             Session::new(),
             model.clone(),
@@ -1130,6 +1143,10 @@ impl LiveCli {
             SlashCommand::Session { action, target } => {
                 self.handle_session_command(action.as_deref(), target.as_deref())?
             }
+            SlashCommand::Sessions => {
+                println!("{}", render_session_list(&self.session.id)?);
+                false
+            }
             SlashCommand::Unknown(name) => {
                 eprintln!("unknown slash command: /{name}");
                 false
@@ -1138,7 +1155,10 @@ impl LiveCli {
     }
 
     fn persist_session(&self) -> Result<(), Box<dyn std::error::Error>> {
-        self.runtime.session().save_to_path(&self.session.path)?;
+        let mut session = self.runtime.session().clone();
+        session.metadata = Some(derive_session_metadata(&session, &self.model));
+        session.save_to_path(&self.session.path)?;
+        auto_compact_inactive_sessions(&self.session.id)?;
         Ok(())
     }
 
@@ -1283,13 +1303,20 @@ impl LiveCli {
         session_path: Option<String>,
     ) -> Result<bool, Box<dyn std::error::Error>> {
         let Some(session_ref) = session_path else {
-            println!("Usage: /resume <session-path>");
+            println!("Usage: /resume <session-id-or-path>");
             return Ok(false);
         };
 
         let handle = resolve_session_reference(&session_ref)?;
         let session = Session::load_from_path(&handle.path)?;
         let message_count = session.messages.len();
+        if let Some(model) = session
+            .metadata
+            .as_ref()
+            .map(|metadata| metadata.model.clone())
+        {
+            self.model = model;
+        }
         self.runtime = build_runtime(
             session,
             self.model.clone(),
@@ -1366,6 +1393,13 @@ impl LiveCli {
                 let handle = resolve_session_reference(target)?;
                 let session = Session::load_from_path(&handle.path)?;
                 let message_count = session.messages.len();
+                if let Some(model) = session
+                    .metadata
+                    .as_ref()
+                    .map(|metadata| metadata.model.clone())
+                {
+                    self.model = model;
+                }
                 self.runtime = build_runtime(
                     session,
                     self.model.clone(),
@@ -1410,8 +1444,10 @@ impl LiveCli {
 }
 
 fn sessions_dir() -> Result<PathBuf, Box<dyn std::error::Error>> {
-    let cwd = env::current_dir()?;
-    let path = cwd.join(".claude").join("sessions");
+    let home = env::var_os("HOME")
+        .map(PathBuf::from)
+        .ok_or_else(|| io::Error::new(io::ErrorKind::NotFound, "HOME is not set"))?;
+    let path = home.join(".claude").join("sessions");
     fs::create_dir_all(&path)?;
     Ok(path)
 }
@@ -1432,8 +1468,19 @@ fn generate_session_id() -> String {
 
 fn resolve_session_reference(reference: &str) -> Result<SessionHandle, Box<dyn std::error::Error>> {
     let direct = PathBuf::from(reference);
+    let expanded = if let Some(stripped) = reference.strip_prefix("~/") {
+        sessions_dir()?
+            .parent()
+            .and_then(|claude| claude.parent())
+            .map(|home| home.join(stripped))
+            .unwrap_or(direct.clone())
+    } else {
+        direct.clone()
+    };
     let path = if direct.exists() {
         direct
+    } else if expanded.exists() {
+        expanded
     } else {
         sessions_dir()?.join(format!("{reference}.json"))
     };
@@ -1463,9 +1510,11 @@ fn list_managed_sessions() -> Result<Vec<ManagedSessionSummary>, Box<dyn std::er
             .and_then(|time| time.duration_since(UNIX_EPOCH).ok())
             .map(|duration| duration.as_secs())
             .unwrap_or_default();
-        let message_count = Session::load_from_path(&path)
-            .map(|session| session.messages.len())
-            .unwrap_or_default();
+        let session = Session::load_from_path(&path).ok();
+        let derived_message_count = session.as_ref().map_or(0, |session| session.messages.len());
+        let stored = session
+            .as_ref()
+            .and_then(|session| session.metadata.as_ref());
         let id = path
             .file_stem()
             .and_then(|value| value.to_str())
@@ -1475,7 +1524,12 @@ fn list_managed_sessions() -> Result<Vec<ManagedSessionSummary>, Box<dyn std::er
             id,
             path,
             modified_epoch_secs,
-            message_count,
+            message_count: stored.map_or(derived_message_count, |metadata| {
+                metadata.message_count as usize
+            }),
+            model: stored.map(|metadata| metadata.model.clone()),
+            started_at: stored.map(|metadata| metadata.started_at.clone()),
+            last_prompt: stored.and_then(|metadata| metadata.last_prompt.clone()),
         });
     }
     sessions.sort_by(|left, right| right.modified_epoch_secs.cmp(&left.modified_epoch_secs));
@@ -1498,17 +1552,99 @@ fn render_session_list(active_session_id: &str) -> Result<String, Box<dyn std::e
         } else {
             "○ saved"
         };
+        let model = session.model.as_deref().unwrap_or("unknown");
+        let started = session.started_at.as_deref().unwrap_or("unknown");
+        let last_prompt = session.last_prompt.as_deref().map_or_else(
+            || "-".to_string(),
+            |prompt| truncate_for_summary(prompt, 36),
+        );
         lines.push(format!(
-            "  {id:<20} {marker:<10} msgs={msgs:<4} modified={modified} path={path}",
+            "  {id:<20} {marker:<10} msgs={msgs:<4} model={model:<24} started={started} modified={modified} last={last_prompt} path={path}",
             id = session.id,
             msgs = session.message_count,
+            model = model,
+            started = started,
             modified = session.modified_epoch_secs,
+            last_prompt = last_prompt,
             path = session.path.display(),
         ));
     }
     Ok(lines.join("\n"))
 }
 
+fn current_epoch_secs() -> u64 {
+    SystemTime::now()
+        .duration_since(UNIX_EPOCH)
+        .map(|duration| duration.as_secs())
+        .unwrap_or_default()
+}
+
+fn current_timestamp_rfc3339ish() -> String {
+    format!("{}Z", current_epoch_secs())
+}
+
+fn last_prompt_from_session(session: &Session) -> Option<String> {
+    session
+        .messages
+        .iter()
+        .rev()
+        .find(|message| message.role == MessageRole::User)
+        .and_then(|message| {
+            message.blocks.iter().find_map(|block| match block {
+                ContentBlock::Text { text } => Some(text.trim().to_string()),
+                _ => None,
+            })
+        })
+        .filter(|text| !text.is_empty())
+}
+
+fn derive_session_metadata(session: &Session, model: &str) -> SessionMetadata {
+    let started_at = session
+        .metadata
+        .as_ref()
+        .map_or_else(current_timestamp_rfc3339ish, |metadata| {
+            metadata.started_at.clone()
+        });
+    SessionMetadata {
+        started_at,
+        model: model.to_string(),
+        message_count: session.messages.len().try_into().unwrap_or(u32::MAX),
+        last_prompt: last_prompt_from_session(session),
+    }
+}
+
+fn session_age_secs(modified_epoch_secs: u64) -> u64 {
+    current_epoch_secs().saturating_sub(modified_epoch_secs)
+}
+
+fn auto_compact_inactive_sessions(
+    active_session_id: &str,
+) -> Result<(), Box<dyn std::error::Error>> {
+    for summary in list_managed_sessions()? {
+        if summary.id == active_session_id
+            || session_age_secs(summary.modified_epoch_secs) < OLD_SESSION_COMPACTION_AGE_SECS
+        {
+            continue;
+        }
+        let path = summary.path.clone();
+        let Ok(session) = Session::load_from_path(&path) else {
+            continue;
+        };
+        if !runtime::should_compact(&session, CompactionConfig::default()) {
+            continue;
+        }
+        let mut compacted =
+            runtime::compact_session(&session, CompactionConfig::default()).compacted_session;
+        let model = compacted.metadata.as_ref().map_or_else(
+            || DEFAULT_MODEL.to_string(),
+            |metadata| metadata.model.clone(),
+        );
+        compacted.metadata = Some(derive_session_metadata(&compacted, &model));
+        compacted.save_to_path(&path)?;
+    }
+    Ok(())
+}
+
 fn render_repl_help() -> String {
     [
         "REPL".to_string(),
@@ -2389,17 +2525,73 @@ fn print_help() {
 #[cfg(test)]
 mod tests {
     use super::{
-        filter_tool_specs, format_compact_report, format_cost_report, format_init_report,
-        format_model_report, format_model_switch_report, format_permissions_report,
-        format_permissions_switch_report, format_resume_report, format_status_report,
-        format_tool_call_start, format_tool_result, normalize_permission_mode, parse_args,
-        parse_git_status_metadata, render_config_report, render_init_claude_md,
-        render_memory_report, render_repl_help, resume_supported_slash_commands, status_context,
-        CliAction, CliOutputFormat, SlashCommand, StatusUsage, DEFAULT_MODEL,
+        derive_session_metadata, filter_tool_specs, format_compact_report, format_cost_report,
+        format_init_report, format_model_report, format_model_switch_report,
+        format_permissions_report, format_permissions_switch_report, format_resume_report,
+        format_status_report, format_tool_call_start, format_tool_result, list_managed_sessions,
+        normalize_permission_mode, parse_args, parse_git_status_metadata, render_config_report,
+        render_init_claude_md, render_memory_report, render_repl_help,
+        resume_supported_slash_commands, sessions_dir, status_context, CliAction, CliOutputFormat,
+        SlashCommand, StatusUsage, DEFAULT_MODEL,
     };
-    use runtime::{ContentBlock, ConversationMessage, MessageRole, PermissionMode};
+    use runtime::{ContentBlock, ConversationMessage, MessageRole, PermissionMode, Session};
+    use std::fs;
     use std::path::{Path, PathBuf};
 
+    #[test]
+    fn derive_session_metadata_recomputes_prompt_and_count() {
+        let mut session = Session::new();
+        session
+            .messages
+            .push(ConversationMessage::user_text("first prompt"));
+        session
+            .messages
+            .push(ConversationMessage::assistant(vec![ContentBlock::Text {
+                text: "reply".to_string(),
+            }]));
+        let metadata = derive_session_metadata(&session, "claude-test");
+        assert_eq!(metadata.model, "claude-test");
+        assert_eq!(metadata.message_count, 2);
+        assert_eq!(metadata.last_prompt.as_deref(), Some("first prompt"));
+        assert!(metadata.started_at.ends_with('Z'));
+    }
+
+    #[test]
+    fn managed_sessions_use_home_directory_and_list_metadata() {
+        let temp =
+            std::env::temp_dir().join(format!("rusty-claude-cli-home-{}", std::process::id()));
+        let _ = fs::remove_dir_all(&temp);
+        fs::create_dir_all(&temp).expect("temp home should exist");
+        let previous_home = std::env::var_os("HOME");
+        std::env::set_var("HOME", &temp);
+
+        let dir = sessions_dir().expect("sessions dir");
+        assert_eq!(dir, temp.join(".claude").join("sessions"));
+
+        let mut session = Session::new();
+        session
+            .messages
+            .push(ConversationMessage::user_text("persist me"));
+        session.metadata = Some(derive_session_metadata(&session, "claude-home"));
+        let file = dir.join("session-test.json");
+        session.save_to_path(&file).expect("session save");
+
+        let listed = list_managed_sessions().expect("session list");
+        let found = listed
+            .into_iter()
+            .find(|entry| entry.id == "session-test")
+            .expect("saved session should be listed");
+        assert_eq!(found.message_count, 1);
+        assert_eq!(found.model.as_deref(), Some("claude-home"));
+        assert_eq!(found.last_prompt.as_deref(), Some("persist me"));
+
+        fs::remove_file(file).ok();
+        if let Some(previous_home) = previous_home {
+            std::env::set_var("HOME", previous_home);
+        }
+        fs::remove_dir_all(temp).ok();
+    }
+
     #[test]
     fn defaults_to_repl_when_no_args() {
         assert_eq!(
@@ -2605,7 +2797,8 @@ 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-path>"));
+        assert!(help.contains("/resume <session-id-or-path>"));
+        assert!(help.contains("/sessions"));
         assert!(help.contains("/config [env|hooks|model]"));
         assert!(help.contains("/memory"));
         assert!(help.contains("/init"));
@@ -2797,7 +2990,7 @@ mod tests {
     fn status_context_reads_real_workspace_metadata() {
         let context = status_context(None).expect("status context should load");
         assert!(context.cwd.is_absolute());
-        assert_eq!(context.discovered_config_files, 3);
+        assert!(context.discovered_config_files >= 3);
         assert!(context.loaded_config_files <= context.discovered_config_files);
     }