wip: jsonl-session progress

rust/crates/commands/src/lib.rs

@@ -392,9 +392,8 @@ mod tests {
 
     #[test]
     fn compacts_sessions_via_slash_command() {
-        let session = Session {
+        let mut session = Session::new();
-            version: 1,
+        session.messages = vec![
-            messages: vec![
             ConversationMessage::user_text("a ".repeat(200)),
             ConversationMessage::assistant(vec![ContentBlock::Text {
                 text: "b ".repeat(200),
@@ -403,8 +402,7 @@ mod tests {
             ConversationMessage::assistant(vec![ContentBlock::Text {
                 text: "recent".to_string(),
             }]),
-            ],
+        ];
-        };
 
         let result = handle_slash_command(
             "/compact",

rust/crates/runtime/src/compact.rs

@@ -99,13 +99,14 @@ pub fn compact_session(session: &Session, config: CompactionConfig) -> Compactio
     }];
     compacted_messages.extend(preserved);
 
+    let mut compacted_session = session.clone();
+    compacted_session.messages = compacted_messages;
+    compacted_session.record_compaction(summary.clone(), removed.len());
+
     CompactionResult {
         summary,
         formatted_summary,
-        compacted_session: Session {
+        compacted_session,
-            version: session.version,
-            messages: compacted_messages,
-        },
         removed_message_count: removed.len(),
     }
 }
@@ -390,10 +391,8 @@ mod tests {
 
     #[test]
     fn leaves_small_sessions_unchanged() {
-        let session = Session {
+        let mut session = Session::new();
-            version: 1,
+        session.messages = vec![ConversationMessage::user_text("hello")];
-            messages: vec![ConversationMessage::user_text("hello")],
-        };
 
         let result = compact_session(&session, CompactionConfig::default());
         assert_eq!(result.removed_message_count, 0);
@@ -404,9 +403,8 @@ mod tests {
 
     #[test]
     fn compacts_older_messages_into_a_system_summary() {
-        let session = Session {
+        let mut session = Session::new();
-            version: 1,
+        session.messages = vec![
-            messages: vec![
             ConversationMessage::user_text("one ".repeat(200)),
             ConversationMessage::assistant(vec![ContentBlock::Text {
                 text: "two ".repeat(200),
@@ -419,8 +417,7 @@ mod tests {
                 }],
                 usage: None,
             },
-            ],
+        ];
-        };
 
         let result = compact_session(
             &session,

rust/crates/runtime/src/conversation.rs

@@ -156,8 +156,8 @@ where
         mut prompter: Option<&mut dyn PermissionPrompter>,
     ) -> Result<TurnSummary, RuntimeError> {
         self.session
-            .messages
+            .push_user_text(user_input.into())
-            .push(ConversationMessage::user_text(user_input.into()));
+            .map_err(|error| RuntimeError::new(error.to_string()))?;
 
         let mut assistant_messages = Vec::new();
         let mut tool_results = Vec::new();
@@ -191,7 +191,9 @@ where
                 })
                 .collect::<Vec<_>>();
 
-            self.session.messages.push(assistant_message.clone());
+            self.session
+                .push_message(assistant_message.clone())
+                .map_err(|error| RuntimeError::new(error.to_string()))?;
             assistant_messages.push(assistant_message);
 
             if pending_tool_uses.is_empty() {
@@ -249,7 +251,9 @@ where
                         ConversationMessage::tool_result(tool_use_id, tool_name, reason, true)
                     }
                 };
-                self.session.messages.push(result_message.clone());
+                self.session
+                    .push_message(result_message.clone())
+                    .map_err(|error| RuntimeError::new(error.to_string()))?;
                 tool_results.push(result_message);
             }
         }
@@ -408,7 +412,9 @@ mod tests {
     use crate::prompt::{ProjectContext, SystemPromptBuilder};
     use crate::session::{ContentBlock, MessageRole, Session};
     use crate::usage::TokenUsage;
+    use std::fs;
     use std::path::PathBuf;
+    use std::time::{SystemTime, UNIX_EPOCH};
 
     struct ScriptedApiClient {
         call_count: usize,
@@ -787,6 +793,57 @@ mod tests {
             result.compacted_session.messages[0].role,
             MessageRole::System
         );
+        assert_eq!(
+            result.compacted_session.session_id,
+            runtime.session().session_id
+        );
+        assert!(result.compacted_session.compaction.is_some());
+    }
+
+    #[test]
+    fn persists_conversation_turn_messages_to_jsonl_session() {
+        struct SimpleApi;
+        impl ApiClient for SimpleApi {
+            fn stream(
+                &mut self,
+                _request: ApiRequest,
+            ) -> Result<Vec<AssistantEvent>, RuntimeError> {
+                Ok(vec![
+                    AssistantEvent::TextDelta("done".to_string()),
+                    AssistantEvent::MessageStop,
+                ])
+            }
+        }
+
+        let path = temp_session_path("persisted-turn");
+        let session = Session::new().with_persistence_path(path.clone());
+        let mut runtime = ConversationRuntime::new(
+            session,
+            SimpleApi,
+            StaticToolExecutor::new(),
+            PermissionPolicy::new(PermissionMode::DangerFullAccess),
+            vec!["system".to_string()],
+        );
+
+        runtime
+            .run_turn("persist this turn", None)
+            .expect("turn should succeed");
+
+        let restored = Session::load_from_path(&path).expect("persisted session should reload");
+        fs::remove_file(&path).expect("temp session file should be removable");
+
+        assert_eq!(restored.messages.len(), 2);
+        assert_eq!(restored.messages[0].role, MessageRole::User);
+        assert_eq!(restored.messages[1].role, MessageRole::Assistant);
+        assert_eq!(restored.session_id, runtime.session().session_id);
+    }
+
+    fn temp_session_path(label: &str) -> PathBuf {
+        let nanos = SystemTime::now()
+            .duration_since(UNIX_EPOCH)
+            .expect("system time should be after epoch")
+            .as_nanos();
+        std::env::temp_dir().join(format!("runtime-conversation-{label}-{nanos}.json"))
     }
 
     #[cfg(windows)]

rust/crates/runtime/src/lib.rs

@@ -76,7 +76,9 @@ 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, SessionCompaction, SessionError,
+};
 pub use usage::{
     format_usd, pricing_for_model, ModelPricing, TokenUsage, UsageCostEstimate, UsageTracker,
 };

rust/crates/runtime/src/session.rs

@@ -1,11 +1,19 @@
 use std::collections::BTreeMap;
 use std::fmt::{Display, Formatter};
-use std::fs;
+use std::fs::{self, OpenOptions};
-use std::path::Path;
+use std::io::Write;
+use std::path::{Path, PathBuf};
+use std::sync::atomic::{AtomicU64, Ordering};
+use std::time::{SystemTime, UNIX_EPOCH};
 
 use crate::json::{JsonError, JsonValue};
 use crate::usage::TokenUsage;
 
+const SESSION_VERSION: u32 = 1;
+const ROTATE_AFTER_BYTES: u64 = 256 * 1024;
+const MAX_ROTATED_FILES: usize = 3;
+static SESSION_ID_COUNTER: AtomicU64 = AtomicU64::new(0);
+
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
 pub enum MessageRole {
     System,
@@ -40,11 +48,41 @@ pub struct ConversationMessage {
 }
 
 #[derive(Debug, Clone, PartialEq, Eq)]
+pub struct SessionCompaction {
+    pub count: u32,
+    pub removed_message_count: usize,
+    pub summary: String,
+}
+
+#[derive(Debug, Clone, PartialEq, Eq)]
+struct SessionPersistence {
+    path: PathBuf,
+}
+
+#[derive(Debug, Clone)]
 pub struct Session {
     pub version: u32,
+    pub session_id: String,
+    pub created_at_ms: u64,
+    pub updated_at_ms: u64,
     pub messages: Vec<ConversationMessage>,
+    pub compaction: Option<SessionCompaction>,
+    persistence: Option<SessionPersistence>,
 }
 
+impl PartialEq for Session {
+    fn eq(&self, other: &Self) -> bool {
+        self.version == other.version
+            && self.session_id == other.session_id
+            && self.created_at_ms == other.created_at_ms
+            && self.updated_at_ms == other.updated_at_ms
+            && self.messages == other.messages
+            && self.compaction == other.compaction
+    }
+}
+
+impl Eq for Session {}
+
 #[derive(Debug)]
 pub enum SessionError {
     Io(std::io::Error),
@@ -79,20 +117,65 @@ impl From<JsonError> for SessionError {
 impl Session {
     #[must_use]
     pub fn new() -> Self {
+        let now = current_time_millis();
         Self {
-            version: 1,
+            version: SESSION_VERSION,
+            session_id: generate_session_id(),
+            created_at_ms: now,
+            updated_at_ms: now,
             messages: Vec::new(),
+            compaction: None,
+            persistence: None,
         }
     }
 
+    #[must_use]
+    pub fn with_persistence_path(mut self, path: impl Into<PathBuf>) -> Self {
+        self.persistence = Some(SessionPersistence { path: path.into() });
+        self
+    }
+
+    #[must_use]
+    pub fn persistence_path(&self) -> Option<&Path> {
+        self.persistence.as_ref().map(|value| value.path.as_path())
+    }
+
     pub fn save_to_path(&self, path: impl AsRef<Path>) -> Result<(), SessionError> {
-        fs::write(path, self.to_json().render())?;
+        let path = path.as_ref();
+        rotate_session_file_if_needed(path)?;
+        write_atomic(path, &self.render_jsonl_snapshot())?;
+        cleanup_rotated_logs(path)?;
         Ok(())
     }
 
     pub fn load_from_path(path: impl AsRef<Path>) -> Result<Self, SessionError> {
+        let path = path.as_ref();
         let contents = fs::read_to_string(path)?;
-        Self::from_json(&JsonValue::parse(&contents)?)
+        let session = match JsonValue::parse(&contents) {
+            Ok(value) => Self::from_json(&value)?,
+            Err(_) => Self::from_jsonl(&contents)?,
+        };
+        Ok(session.with_persistence_path(path.to_path_buf()))
+    }
+
+    pub fn push_message(&mut self, message: ConversationMessage) -> Result<(), SessionError> {
+        self.touch();
+        self.messages.push(message.clone());
+        self.append_persisted_message(&message)
+    }
+
+    pub fn push_user_text(&mut self, text: impl Into<String>) -> Result<(), SessionError> {
+        self.push_message(ConversationMessage::user_text(text))
+    }
+
+    pub fn record_compaction(&mut self, summary: impl Into<String>, removed_message_count: usize) {
+        self.touch();
+        let count = self.compaction.as_ref().map_or(1, |value| value.count + 1);
+        self.compaction = Some(SessionCompaction {
+            count,
+            removed_message_count,
+            summary: summary.into(),
+        });
     }
 
     #[must_use]
@@ -102,6 +185,18 @@ impl Session {
             "version".to_string(),
             JsonValue::Number(i64::from(self.version)),
         );
+        object.insert(
+            "session_id".to_string(),
+            JsonValue::String(self.session_id.clone()),
+        );
+        object.insert(
+            "created_at_ms".to_string(),
+            JsonValue::Number(i64_from_u64(self.created_at_ms, "created_at_ms")),
+        );
+        object.insert(
+            "updated_at_ms".to_string(),
+            JsonValue::Number(i64_from_u64(self.updated_at_ms, "updated_at_ms")),
+        );
         object.insert(
             "messages".to_string(),
             JsonValue::Array(
@@ -111,6 +206,9 @@ impl Session {
                     .collect(),
             ),
         );
+        if let Some(compaction) = &self.compaction {
+            object.insert("compaction".to_string(), compaction.to_json());
+        }
         JsonValue::Object(object)
     }
 
@@ -131,7 +229,171 @@ impl Session {
             .iter()
             .map(ConversationMessage::from_json)
             .collect::<Result<Vec<_>, _>>()?;
-        Ok(Self { version, messages })
+        let now = current_time_millis();
+        let session_id = object
+            .get("session_id")
+            .and_then(JsonValue::as_str)
+            .map(ToOwned::to_owned)
+            .unwrap_or_else(generate_session_id);
+        let created_at_ms = object
+            .get("created_at_ms")
+            .map(|value| required_u64_from_value(value, "created_at_ms"))
+            .transpose()?
+            .unwrap_or(now);
+        let updated_at_ms = object
+            .get("updated_at_ms")
+            .map(|value| required_u64_from_value(value, "updated_at_ms"))
+            .transpose()?
+            .unwrap_or(created_at_ms);
+        let compaction = object
+            .get("compaction")
+            .map(SessionCompaction::from_json)
+            .transpose()?;
+        Ok(Self {
+            version,
+            session_id,
+            created_at_ms,
+            updated_at_ms,
+            messages,
+            compaction,
+            persistence: None,
+        })
+    }
+
+    fn from_jsonl(contents: &str) -> Result<Self, SessionError> {
+        let mut version = SESSION_VERSION;
+        let mut session_id = None;
+        let mut created_at_ms = None;
+        let mut updated_at_ms = None;
+        let mut messages = Vec::new();
+        let mut compaction = None;
+
+        for (line_number, raw_line) in contents.lines().enumerate() {
+            let line = raw_line.trim();
+            if line.is_empty() {
+                continue;
+            }
+            let value = JsonValue::parse(line).map_err(|error| {
+                SessionError::Format(format!(
+                    "invalid JSONL record at line {}: {}",
+                    line_number + 1,
+                    error
+                ))
+            })?;
+            let object = value.as_object().ok_or_else(|| {
+                SessionError::Format(format!(
+                    "JSONL record at line {} must be an object",
+                    line_number + 1
+                ))
+            })?;
+            match object
+                .get("type")
+                .and_then(JsonValue::as_str)
+                .ok_or_else(|| {
+                    SessionError::Format(format!(
+                        "JSONL record at line {} missing type",
+                        line_number + 1
+                    ))
+                })? {
+                "session_meta" => {
+                    version = required_u32(object, "version")?;
+                    session_id = Some(required_string(object, "session_id")?);
+                    created_at_ms = Some(required_u64(object, "created_at_ms")?);
+                    updated_at_ms = Some(required_u64(object, "updated_at_ms")?);
+                }
+                "message" => {
+                    let message_value = object.get("message").ok_or_else(|| {
+                        SessionError::Format(format!(
+                            "JSONL record at line {} missing message",
+                            line_number + 1
+                        ))
+                    })?;
+                    messages.push(ConversationMessage::from_json(message_value)?);
+                }
+                "compaction" => {
+                    compaction = Some(SessionCompaction::from_json(&JsonValue::Object(
+                        object.clone(),
+                    ))?);
+                }
+                other => {
+                    return Err(SessionError::Format(format!(
+                        "unsupported JSONL record type at line {}: {other}",
+                        line_number + 1
+                    )))
+                }
+            }
+        }
+
+        let now = current_time_millis();
+        Ok(Self {
+            version,
+            session_id: session_id.unwrap_or_else(generate_session_id),
+            created_at_ms: created_at_ms.unwrap_or(now),
+            updated_at_ms: updated_at_ms.unwrap_or(created_at_ms.unwrap_or(now)),
+            messages,
+            compaction,
+            persistence: None,
+        })
+    }
+
+    fn render_jsonl_snapshot(&self) -> String {
+        let mut lines = vec![self.meta_record().render()];
+        if let Some(compaction) = &self.compaction {
+            lines.push(compaction.to_jsonl_record().render());
+        }
+        lines.extend(
+            self.messages
+                .iter()
+                .map(|message| message_record(message).render()),
+        );
+        let mut rendered = lines.join("\n");
+        rendered.push('\n');
+        rendered
+    }
+
+    fn append_persisted_message(&self, message: &ConversationMessage) -> Result<(), SessionError> {
+        let Some(path) = self.persistence_path() else {
+            return Ok(());
+        };
+
+        let needs_bootstrap = !path.exists() || fs::metadata(path)?.len() == 0;
+        if needs_bootstrap {
+            self.save_to_path(path)?;
+            return Ok(());
+        }
+
+        let mut file = OpenOptions::new().append(true).open(path)?;
+        writeln!(file, "{}", message_record(message).render())?;
+        Ok(())
+    }
+
+    fn meta_record(&self) -> JsonValue {
+        let mut object = BTreeMap::new();
+        object.insert(
+            "type".to_string(),
+            JsonValue::String("session_meta".to_string()),
+        );
+        object.insert(
+            "version".to_string(),
+            JsonValue::Number(i64::from(self.version)),
+        );
+        object.insert(
+            "session_id".to_string(),
+            JsonValue::String(self.session_id.clone()),
+        );
+        object.insert(
+            "created_at_ms".to_string(),
+            JsonValue::Number(i64_from_u64(self.created_at_ms, "created_at_ms")),
+        );
+        object.insert(
+            "updated_at_ms".to_string(),
+            JsonValue::Number(i64_from_u64(self.updated_at_ms, "updated_at_ms")),
+        );
+        JsonValue::Object(object)
+    }
+
+    fn touch(&mut self) {
+        self.updated_at_ms = current_time_millis();
     }
 }
 
@@ -324,6 +586,61 @@ impl ContentBlock {
     }
 }
 
+impl SessionCompaction {
+    #[must_use]
+    pub fn to_json(&self) -> JsonValue {
+        let mut object = BTreeMap::new();
+        object.insert(
+            "count".to_string(),
+            JsonValue::Number(i64::from(self.count)),
+        );
+        object.insert(
+            "removed_message_count".to_string(),
+            JsonValue::Number(i64_from_usize(
+                self.removed_message_count,
+                "removed_message_count",
+            )),
+        );
+        object.insert(
+            "summary".to_string(),
+            JsonValue::String(self.summary.clone()),
+        );
+        JsonValue::Object(object)
+    }
+
+    #[must_use]
+    pub fn to_jsonl_record(&self) -> JsonValue {
+        let mut object = self
+            .to_json()
+            .as_object()
+            .cloned()
+            .expect("compaction should render to object");
+        object.insert(
+            "type".to_string(),
+            JsonValue::String("compaction".to_string()),
+        );
+        JsonValue::Object(object)
+    }
+
+    fn from_json(value: &JsonValue) -> Result<Self, SessionError> {
+        let object = value
+            .as_object()
+            .ok_or_else(|| SessionError::Format("compaction must be an object".to_string()))?;
+        Ok(Self {
+            count: required_u32(object, "count")?,
+            removed_message_count: required_usize(object, "removed_message_count")?,
+            summary: required_string(object, "summary")?,
+        })
+    }
+}
+
+fn message_record(message: &ConversationMessage) -> JsonValue {
+    let mut object = BTreeMap::new();
+    object.insert("type".to_string(), JsonValue::String("message".to_string()));
+    object.insert("message".to_string(), message.to_json());
+    JsonValue::Object(object)
+}
+
 fn usage_to_json(usage: TokenUsage) -> JsonValue {
     let mut object = BTreeMap::new();
     object.insert(
@@ -376,22 +693,144 @@ fn required_u32(object: &BTreeMap<String, JsonValue>, key: &str) -> Result<u32,
     u32::try_from(value).map_err(|_| SessionError::Format(format!("{key} out of range")))
 }
 
+fn required_u64(object: &BTreeMap<String, JsonValue>, key: &str) -> Result<u64, SessionError> {
+    let value = object
+        .get(key)
+        .ok_or_else(|| SessionError::Format(format!("missing {key}")))?;
+    required_u64_from_value(value, key)
+}
+
+fn required_u64_from_value(value: &JsonValue, key: &str) -> Result<u64, SessionError> {
+    let value = value
+        .as_i64()
+        .ok_or_else(|| SessionError::Format(format!("missing {key}")))?;
+    u64::try_from(value).map_err(|_| SessionError::Format(format!("{key} out of range")))
+}
+
+fn required_usize(object: &BTreeMap<String, JsonValue>, key: &str) -> Result<usize, SessionError> {
+    let value = object
+        .get(key)
+        .and_then(JsonValue::as_i64)
+        .ok_or_else(|| SessionError::Format(format!("missing {key}")))?;
+    usize::try_from(value).map_err(|_| SessionError::Format(format!("{key} out of range")))
+}
+
+fn i64_from_u64(value: u64, key: &str) -> i64 {
+    i64::try_from(value).unwrap_or_else(|_| panic!("{key} out of range for JSON number"))
+}
+
+fn i64_from_usize(value: usize, key: &str) -> i64 {
+    i64::try_from(value).unwrap_or_else(|_| panic!("{key} out of range for JSON number"))
+}
+
+fn current_time_millis() -> u64 {
+    SystemTime::now()
+        .duration_since(UNIX_EPOCH)
+        .map(|duration| duration.as_millis() as u64)
+        .unwrap_or_default()
+}
+
+fn generate_session_id() -> String {
+    let millis = current_time_millis();
+    let counter = SESSION_ID_COUNTER.fetch_add(1, Ordering::Relaxed);
+    format!("session-{millis}-{counter}")
+}
+
+fn write_atomic(path: &Path, contents: &str) -> Result<(), SessionError> {
+    if let Some(parent) = path.parent() {
+        fs::create_dir_all(parent)?;
+    }
+    let temp_path = temporary_path_for(path);
+    fs::write(&temp_path, contents)?;
+    fs::rename(temp_path, path)?;
+    Ok(())
+}
+
+fn temporary_path_for(path: &Path) -> PathBuf {
+    let file_name = path
+        .file_name()
+        .and_then(|value| value.to_str())
+        .unwrap_or("session");
+    path.with_file_name(format!(
+        "{file_name}.tmp-{}-{}",
+        current_time_millis(),
+        SESSION_ID_COUNTER.fetch_add(1, Ordering::Relaxed)
+    ))
+}
+
+fn rotate_session_file_if_needed(path: &Path) -> Result<(), SessionError> {
+    let Ok(metadata) = fs::metadata(path) else {
+        return Ok(());
+    };
+    if metadata.len() < ROTATE_AFTER_BYTES {
+        return Ok(());
+    }
+    let rotated_path = rotated_log_path(path);
+    fs::rename(path, rotated_path)?;
+    Ok(())
+}
+
+fn rotated_log_path(path: &Path) -> PathBuf {
+    let stem = path
+        .file_stem()
+        .and_then(|value| value.to_str())
+        .unwrap_or("session");
+    path.with_file_name(format!("{stem}.rot-{}.jsonl", current_time_millis()))
+}
+
+fn cleanup_rotated_logs(path: &Path) -> Result<(), SessionError> {
+    let Some(parent) = path.parent() else {
+        return Ok(());
+    };
+    let stem = path
+        .file_stem()
+        .and_then(|value| value.to_str())
+        .unwrap_or("session");
+    let prefix = format!("{stem}.rot-");
+    let mut rotated_paths = fs::read_dir(parent)?
+        .filter_map(Result::ok)
+        .map(|entry| entry.path())
+        .filter(|entry_path| {
+            entry_path
+                .file_name()
+                .and_then(|value| value.to_str())
+                .is_some_and(|name| name.starts_with(&prefix) && name.ends_with(".jsonl"))
+        })
+        .collect::<Vec<_>>();
+
+    rotated_paths.sort_by_key(|entry_path| {
+        fs::metadata(entry_path)
+            .and_then(|metadata| metadata.modified())
+            .unwrap_or(UNIX_EPOCH)
+    });
+
+    let remove_count = rotated_paths.len().saturating_sub(MAX_ROTATED_FILES);
+    for stale_path in rotated_paths.into_iter().take(remove_count) {
+        fs::remove_file(stale_path)?;
+    }
+    Ok(())
+}
+
 #[cfg(test)]
 mod tests {
-    use super::{ContentBlock, ConversationMessage, MessageRole, Session};
+    use super::{
+        cleanup_rotated_logs, rotate_session_file_if_needed, ContentBlock, ConversationMessage,
+        MessageRole, Session,
+    };
+    use crate::json::JsonValue;
     use crate::usage::TokenUsage;
     use std::fs;
+    use std::path::PathBuf;
     use std::time::{SystemTime, UNIX_EPOCH};
 
     #[test]
-    fn persists_and_restores_session_json() {
+    fn persists_and_restores_session_jsonl() {
         let mut session = Session::new();
         session
-            .messages
+            .push_user_text("hello")
-            .push(ConversationMessage::user_text("hello"));
+            .expect("user message should append");
         session
-            .messages
+            .push_message(ConversationMessage::assistant_with_usage(
-            .push(ConversationMessage::assistant_with_usage(
                 vec![
                     ContentBlock::Text {
                         text: "thinking".to_string(),
@@ -408,16 +847,15 @@ mod tests {
                     cache_creation_input_tokens: 1,
                     cache_read_input_tokens: 2,
                 }),
-            ));
+            ))
-        session.messages.push(ConversationMessage::tool_result(
+            .expect("assistant message should append");
+        session
+            .push_message(ConversationMessage::tool_result(
                 "tool-1", "bash", "hi", false,
-        ));
+            ))
+            .expect("tool result should append");
 
-        let nanos = SystemTime::now()
+        let path = temp_session_path("jsonl");
-            .duration_since(UNIX_EPOCH)
-            .expect("system time should be after epoch")
-            .as_nanos();
-        let path = std::env::temp_dir().join(format!("runtime-session-{nanos}.json"));
         session.save_to_path(&path).expect("session should save");
         let restored = Session::load_from_path(&path).expect("session should load");
         fs::remove_file(&path).expect("temp file should be removable");
@@ -428,5 +866,128 @@ mod tests {
             restored.messages[1].usage.expect("usage").total_tokens(),
             17
         );
+        assert_eq!(restored.session_id, session.session_id);
+    }
+
+    #[test]
+    fn loads_legacy_session_json_object() {
+        let path = temp_session_path("legacy");
+        let legacy = JsonValue::Object(
+            [
+                ("version".to_string(), JsonValue::Number(1)),
+                (
+                    "messages".to_string(),
+                    JsonValue::Array(vec![ConversationMessage::user_text("legacy").to_json()]),
+                ),
+            ]
+            .into_iter()
+            .collect(),
+        );
+        fs::write(&path, legacy.render()).expect("legacy file should write");
+
+        let restored = Session::load_from_path(&path).expect("legacy session should load");
+        fs::remove_file(&path).expect("temp file should be removable");
+
+        assert_eq!(restored.messages.len(), 1);
+        assert_eq!(
+            restored.messages[0],
+            ConversationMessage::user_text("legacy")
+        );
+        assert!(!restored.session_id.is_empty());
+    }
+
+    #[test]
+    fn appends_messages_to_persisted_jsonl_session() {
+        let path = temp_session_path("append");
+        let mut session = Session::new().with_persistence_path(path.clone());
+        session
+            .save_to_path(&path)
+            .expect("initial save should succeed");
+        session
+            .push_user_text("hi")
+            .expect("user append should succeed");
+        session
+            .push_message(ConversationMessage::assistant(vec![ContentBlock::Text {
+                text: "hello".to_string(),
+            }]))
+            .expect("assistant append should succeed");
+
+        let restored = Session::load_from_path(&path).expect("session should replay from jsonl");
+        fs::remove_file(&path).expect("temp file should be removable");
+
+        assert_eq!(restored.messages.len(), 2);
+        assert_eq!(restored.messages[0], ConversationMessage::user_text("hi"));
+    }
+
+    #[test]
+    fn persists_compaction_metadata() {
+        let path = temp_session_path("compaction");
+        let mut session = Session::new();
+        session
+            .push_user_text("before")
+            .expect("message should append");
+        session.record_compaction("summarized earlier work", 4);
+        session.save_to_path(&path).expect("session should save");
+
+        let restored = Session::load_from_path(&path).expect("session should load");
+        fs::remove_file(&path).expect("temp file should be removable");
+
+        let compaction = restored.compaction.expect("compaction metadata");
+        assert_eq!(compaction.count, 1);
+        assert_eq!(compaction.removed_message_count, 4);
+        assert!(compaction.summary.contains("summarized"));
+    }
+
+    #[test]
+    fn rotates_and_cleans_up_large_session_logs() {
+        let path = temp_session_path("rotation");
+        fs::write(&path, "x".repeat((super::ROTATE_AFTER_BYTES + 10) as usize))
+            .expect("oversized file should write");
+        rotate_session_file_if_needed(&path).expect("rotation should succeed");
+        assert!(
+            !path.exists(),
+            "original path should be rotated away before rewrite"
+        );
+
+        for _ in 0..5 {
+            let rotated = super::rotated_log_path(&path);
+            fs::write(&rotated, "old").expect("rotated file should write");
+        }
+        cleanup_rotated_logs(&path).expect("cleanup should succeed");
+
+        let rotated_count = rotation_files(&path).len();
+        assert!(rotated_count <= super::MAX_ROTATED_FILES);
+        for rotated in rotation_files(&path) {
+            fs::remove_file(rotated).expect("rotated file should be removable");
+        }
+    }
+
+    fn temp_session_path(label: &str) -> PathBuf {
+        let nanos = SystemTime::now()
+            .duration_since(UNIX_EPOCH)
+            .expect("system time should be after epoch")
+            .as_nanos();
+        std::env::temp_dir().join(format!("runtime-session-{label}-{nanos}.json"))
+    }
+
+    fn rotation_files(path: &PathBuf) -> Vec<PathBuf> {
+        let stem = path
+            .file_stem()
+            .and_then(|value| value.to_str())
+            .expect("temp path should have file stem")
+            .to_string();
+        fs::read_dir(path.parent().expect("temp path should have parent"))
+            .expect("temp dir should read")
+            .filter_map(Result::ok)
+            .map(|entry| entry.path())
+            .filter(|entry_path| {
+                entry_path
+                    .file_name()
+                    .and_then(|value| value.to_str())
+                    .is_some_and(|name| {
+                        name.starts_with(&format!("{stem}.rot-")) && name.ends_with(".jsonl")
+                    })
+            })
+            .collect()
     }
 }

rust/crates/runtime/src/usage.rs

@@ -286,9 +286,8 @@ mod tests {
 
     #[test]
     fn reconstructs_usage_from_session_messages() {
-        let session = Session {
+        let mut session = Session::new();
-            version: 1,
+        session.messages = vec![ConversationMessage {
-            messages: vec![ConversationMessage {
             role: MessageRole::Assistant,
             blocks: vec![ContentBlock::Text {
                 text: "done".to_string(),
@@ -299,8 +298,7 @@ mod tests {
                 cache_creation_input_tokens: 1,
                 cache_read_input_tokens: 0,
             }),
-            }],
+        }];
-        };
 
         let tracker = UsageTracker::from_session(&session);
         assert_eq!(tracker.turns(), 1);

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

@@ -9,7 +9,7 @@ use std::io::{self, Read, Write};
 use std::net::TcpListener;
 use std::path::{Path, PathBuf};
 use std::process::Command;
-use std::time::{SystemTime, UNIX_EPOCH};
+use std::time::UNIX_EPOCH;
 
 use api::{
     resolve_startup_auth_source, AnthropicClient, AuthSource, ContentBlockDelta, InputContentBlock,
@@ -992,9 +992,10 @@ impl LiveCli {
         permission_mode: PermissionMode,
     ) -> Result<Self, Box<dyn std::error::Error>> {
         let system_prompt = build_system_prompt()?;
-        let session = create_managed_session_handle()?;
+        let session_state = Session::new();
+        let session = create_managed_session_handle(&session_state.session_id)?;
         let runtime = build_runtime(
-            Session::new(),
+            session_state.with_persistence_path(session.path.clone()),
             model.clone(),
             system_prompt.clone(),
             enable_tools,
@@ -1297,9 +1298,10 @@ impl LiveCli {
             return Ok(false);
         }
 
-        self.session = create_managed_session_handle()?;
+        let session_state = Session::new();
+        self.session = create_managed_session_handle(&session_state.session_id)?;
         self.runtime = build_runtime(
-            Session::new(),
+            session_state.with_persistence_path(self.session.path.clone()),
             self.model.clone(),
             self.system_prompt.clone(),
             true,
@@ -1333,6 +1335,7 @@ impl LiveCli {
         let handle = resolve_session_reference(&session_ref)?;
         let session = Session::load_from_path(&handle.path)?;
         let message_count = session.messages.len();
+        let session_id = session.session_id.clone();
         self.runtime = build_runtime(
             session,
             self.model.clone(),
@@ -1342,7 +1345,10 @@ impl LiveCli {
             self.allowed_tools.clone(),
             self.permission_mode,
         )?;
-        self.session = handle;
+        self.session = SessionHandle {
+            id: session_id,
+            path: handle.path,
+        };
         println!(
             "{}",
             format_resume_report(
@@ -1405,6 +1411,7 @@ impl LiveCli {
                 let handle = resolve_session_reference(target)?;
                 let session = Session::load_from_path(&handle.path)?;
                 let message_count = session.messages.len();
+                let session_id = session.session_id.clone();
                 self.runtime = build_runtime(
                     session,
                     self.model.clone(),
@@ -1414,7 +1421,10 @@ impl LiveCli {
                     self.allowed_tools.clone(),
                     self.permission_mode,
                 )?;
-                self.session = handle;
+                self.session = SessionHandle {
+                    id: session_id,
+                    path: handle.path,
+                };
                 println!(
                     "Session switched\n  Active session   {}\n  File             {}\n  Messages         {}",
                     self.session.id,
@@ -1457,20 +1467,14 @@ fn sessions_dir() -> Result<PathBuf, Box<dyn std::error::Error>> {
     Ok(path)
 }
 
-fn create_managed_session_handle() -> Result<SessionHandle, Box<dyn std::error::Error>> {
+fn create_managed_session_handle(
-    let id = generate_session_id();
+    session_id: &str,
+) -> Result<SessionHandle, Box<dyn std::error::Error>> {
+    let id = session_id.to_string();
     let path = sessions_dir()?.join(format!("{id}.json"));
     Ok(SessionHandle { id, path })
 }
 
-fn generate_session_id() -> String {
-    let millis = SystemTime::now()
-        .duration_since(UNIX_EPOCH)
-        .map(|duration| duration.as_millis())
-        .unwrap_or_default();
-    format!("session-{millis}")
-}
-
 fn resolve_session_reference(reference: &str) -> Result<SessionHandle, Box<dyn std::error::Error>> {
     let direct = PathBuf::from(reference);
     let path = if direct.exists() {
@@ -1504,14 +1508,17 @@ 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)
+        let (id, message_count) = Session::load_from_path(&path)
-            .map(|session| session.messages.len())
+            .map(|session| (session.session_id, session.messages.len()))
-            .unwrap_or_default();
+            .unwrap_or_else(|_| {
-        let id = path
+                (
-            .file_stem()
+                    path.file_stem()
                         .and_then(|value| value.to_str())
                         .unwrap_or("unknown")
-            .to_string();
+                        .to_string(),
+                    0,
+                )
+            });
         sessions.push(ManagedSessionSummary {
             id,
             path,