diff --git a/src-tauri/src/commands.rs b/src-tauri/src/commands.rs
index 030e0ab..32c96ea 100644
--- a/src-tauri/src/commands.rs
+++ b/src-tauri/src/commands.rs
@@ -1464,6 +1464,7 @@ pub async fn close_application(app_handle: AppHandle) -> Result<(), String> {
 pub struct MemoryFileInfo {
     pub path: String,
     pub heading: Option<String>,
+    pub last_modified: Option<String>, // Unix timestamp in seconds as a string
 }
 
 #[derive(serde::Serialize)]
@@ -1535,7 +1536,11 @@ async fn list_memory_files_via_wsl() -> Result<MemoryFilesResponse, String> {
     let mut files = Vec::new();
     for path in paths {
         let heading = read_wsl_file_first_heading(&path);
-        files.push(MemoryFileInfo { path, heading });
+        files.push(MemoryFileInfo {
+            path,
+            heading,
+            last_modified: None,
+        });
     }
 
     Ok(MemoryFilesResponse { files })
@@ -1605,14 +1610,23 @@ async fn list_memory_files_native() -> Result<MemoryFilesResponse, String> {
     // Sort files alphabetically
     memory_paths.sort();
 
-    // Read first heading from each file
+    // Read first heading and modification time from each file
     let files = memory_paths
         .into_iter()
         .map(|path| {
             let heading = fs::read_to_string(&path)
                 .ok()
                 .and_then(|content| extract_first_heading(&content));
-            MemoryFileInfo { path, heading }
+            let last_modified = fs::metadata(&path)
+                .ok()
+                .and_then(|m| m.modified().ok())
+                .and_then(|t| t.duration_since(std::time::UNIX_EPOCH).ok())
+                .map(|d| d.as_secs().to_string());
+            MemoryFileInfo {
+                path,
+                heading,
+                last_modified,
+            }
         })
         .collect();
 
diff --git a/src-tauri/src/config.rs b/src-tauri/src/config.rs
index ab26da7..2fb18f4 100644
--- a/src-tauri/src/config.rs
+++ b/src-tauri/src/config.rs
@@ -51,6 +51,9 @@ pub struct ClaudeStartOptions {
 
     #[serde(default)]
     pub model_overrides: Option<HashMap<String, String>>,
+
+    #[serde(default)]
+    pub session_name: Option<String>,
 }
 
 #[derive(Debug, Clone, Serialize, Deserialize)]
diff --git a/src-tauri/src/types.rs b/src-tauri/src/types.rs
index f73cb4b..73a1f57 100644
--- a/src-tauri/src/types.rs
+++ b/src-tauri/src/types.rs
@@ -280,6 +280,44 @@ pub struct UserQuestionEvent {
     pub conversation_id: Option<String>,
 }
 
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ElicitationEvent {
+    pub message: String,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub server_name: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub request_id: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub conversation_id: Option<String>,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ElicitationResultEvent {
+    pub action: String,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub request_id: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub conversation_id: Option<String>,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct StopFailureEvent {
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub stop_reason: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub error_type: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub conversation_id: Option<String>,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct PostCompactEvent {
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub session_id: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub conversation_id: Option<String>,
+}
+
 #[derive(Debug, Clone, Serialize, Deserialize)]
 pub struct AgentStartEvent {
     pub tool_use_id: String,
@@ -566,4 +604,141 @@ mod tests {
             panic!("Expected RateLimitEvent variant");
         }
     }
+
+    #[test]
+    fn test_elicitation_event_serialization() {
+        let event = ElicitationEvent {
+            message: "Please provide the API endpoint".to_string(),
+            server_name: Some("my-server".to_string()),
+            request_id: Some("req-123".to_string()),
+            conversation_id: Some("conv-abc".to_string()),
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"message\":\"Please provide the API endpoint\""));
+        assert!(serialized.contains("\"server_name\":\"my-server\""));
+        assert!(serialized.contains("\"request_id\":\"req-123\""));
+        assert!(serialized.contains("\"conversation_id\":\"conv-abc\""));
+    }
+
+    #[test]
+    fn test_elicitation_event_omits_none_fields() {
+        let event = ElicitationEvent {
+            message: "Enter your token".to_string(),
+            server_name: None,
+            request_id: None,
+            conversation_id: None,
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"message\":\"Enter your token\""));
+        assert!(!serialized.contains("server_name"));
+        assert!(!serialized.contains("request_id"));
+        assert!(!serialized.contains("conversation_id"));
+    }
+
+    #[test]
+    fn test_elicitation_result_event_serialization() {
+        let event = ElicitationResultEvent {
+            action: "accept".to_string(),
+            request_id: Some("req-123".to_string()),
+            conversation_id: Some("conv-abc".to_string()),
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"action\":\"accept\""));
+        assert!(serialized.contains("\"request_id\":\"req-123\""));
+    }
+
+    #[test]
+    fn test_elicitation_result_event_cancel_omits_none_fields() {
+        let event = ElicitationResultEvent {
+            action: "cancel".to_string(),
+            request_id: None,
+            conversation_id: None,
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"action\":\"cancel\""));
+        assert!(!serialized.contains("request_id"));
+        assert!(!serialized.contains("conversation_id"));
+    }
+
+    #[test]
+    fn test_stop_failure_event_serialization() {
+        let event = StopFailureEvent {
+            stop_reason: Some("api_error".to_string()),
+            error_type: Some("rate_limit".to_string()),
+            conversation_id: Some("conv-abc".to_string()),
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"stop_reason\":\"api_error\""));
+        assert!(serialized.contains("\"error_type\":\"rate_limit\""));
+        assert!(serialized.contains("\"conversation_id\":\"conv-abc\""));
+    }
+
+    #[test]
+    fn test_stop_failure_event_omits_none_fields() {
+        let event = StopFailureEvent {
+            stop_reason: None,
+            error_type: None,
+            conversation_id: None,
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(!serialized.contains("stop_reason"));
+        assert!(!serialized.contains("error_type"));
+        assert!(!serialized.contains("conversation_id"));
+    }
+
+    #[test]
+    fn test_stop_failure_event_partial_fields() {
+        let event = StopFailureEvent {
+            stop_reason: Some("api_error".to_string()),
+            error_type: None,
+            conversation_id: None,
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"stop_reason\":\"api_error\""));
+        assert!(!serialized.contains("error_type"));
+        assert!(!serialized.contains("conversation_id"));
+    }
+
+    #[test]
+    fn test_post_compact_event_serialization() {
+        let event = PostCompactEvent {
+            session_id: Some("sess-abc".to_string()),
+            conversation_id: Some("conv-123".to_string()),
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"session_id\":\"sess-abc\""));
+        assert!(serialized.contains("\"conversation_id\":\"conv-123\""));
+    }
+
+    #[test]
+    fn test_post_compact_event_omits_none_fields() {
+        let event = PostCompactEvent {
+            session_id: None,
+            conversation_id: None,
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(!serialized.contains("session_id"));
+        assert!(!serialized.contains("conversation_id"));
+    }
+
+    #[test]
+    fn test_post_compact_event_partial_fields() {
+        let event = PostCompactEvent {
+            session_id: Some("sess-xyz".to_string()),
+            conversation_id: None,
+        };
+
+        let serialized = serde_json::to_string(&event).unwrap();
+        assert!(serialized.contains("\"session_id\":\"sess-xyz\""));
+        assert!(!serialized.contains("conversation_id"));
+    }
 }
diff --git a/src-tauri/src/wsl_bridge.rs b/src-tauri/src/wsl_bridge.rs
index 1d720c8..1eef472 100644
--- a/src-tauri/src/wsl_bridge.rs
+++ b/src-tauri/src/wsl_bridge.rs
@@ -15,9 +15,10 @@ use crate::process_ext::HideWindow;
 use crate::stats::{calculate_cost, StatsUpdateEvent, UsageStats};
 use crate::types::{
     AgentEndEvent, AgentStartEvent, CharacterState, ClaudeMessage, ConnectionEvent,
-    ConnectionStatus, ContentBlock, MessageCost, OutputEvent, PermissionPromptEvent,
-    PermissionPromptEventItem, QuestionOption, SessionEvent, StateChangeEvent, TodoItem,
-    TodoUpdateEvent, UserQuestionEvent, WorkingDirectoryEvent, WorktreeEvent, WorktreeInfo,
+    ConnectionStatus, ContentBlock, ElicitationEvent, ElicitationResultEvent, MessageCost,
+    OutputEvent, PermissionPromptEvent, PermissionPromptEventItem, QuestionOption, SessionEvent,
+    PostCompactEvent, StateChangeEvent, StopFailureEvent, TodoItem, TodoUpdateEvent,
+    UserQuestionEvent, WorkingDirectoryEvent, WorktreeEvent, WorktreeInfo,
 };
 use parking_lot::RwLock;
 use std::cell::RefCell;
@@ -286,6 +287,13 @@ impl WslBridge {
                 }
             }
 
+            // Pass session name to Claude Code if specified
+            if let Some(ref name) = options.session_name {
+                if !name.is_empty() {
+                    cmd.args(["--name", name]);
+                }
+            }
+
             // Add worktree flag if requested
             if options.use_worktree {
                 cmd.arg("--worktree");
@@ -465,6 +473,14 @@ impl WslBridge {
                 }
             }
 
+            // Pass session name to Claude Code if specified
+            if let Some(ref name) = options.session_name {
+                if !name.is_empty() {
+                    let escaped = name.replace('\'', "'\\''");
+                    claude_cmd.push_str(&format!(" --name '{}'", escaped));
+                }
+            }
+
             // Add worktree flag if requested
             if options.use_worktree {
                 claude_cmd.push_str(" --worktree");
@@ -587,12 +603,13 @@ impl WslBridge {
         );
 
         // Watchdog: if system:init never arrives the process is truly hung (e.g. a silent crash
-        // after spawning).  After 5 minutes we kill it so the user isn't stuck forever.
-        // handle_stdout will surface the error when stdout closes after the kill.
+        // after spawning). After 30 seconds we kill it so the user is not stuck forever.
+        // The CLI v2.1.79 stdin-hang fix means startup is reliably fast; 30 s is a generous
+        // safety net rather than a workaround for a known hang.
         let process_watchdog = self.process.clone();
         let received_init_watchdog = self.received_init.clone();
         thread::spawn(move || {
-            thread::sleep(Duration::from_secs(60));
+            thread::sleep(Duration::from_secs(30));
             if !received_init_watchdog.load(Ordering::SeqCst) {
                 if let Some(mut proc) = process_watchdog.lock().take() {
                     let _ = proc.kill();
@@ -613,6 +630,9 @@ impl WslBridge {
         let process_mid_watchdog = self.process.clone();
         let pending_since_watchdog = self.pending_since.clone();
         let generation_watchdog = self.watchdog_generation.clone();
+        // 5-minute stuck timeout is intentionally larger than the CLI's 2-minute per-attempt
+        // non-streaming fallback (added in v2.1.79). A non-streaming response will either
+        // succeed or fail with a Result message well within this window.
         const STUCK_TIMEOUT: Duration = Duration::from_secs(5 * 60);
         const POLL_INTERVAL: Duration = Duration::from_secs(30);
         thread::spawn(move || {
@@ -783,14 +803,17 @@ impl WslBridge {
             }
 
             let input_chars = stats.current_request_input.as_ref().map(|s| s.len() as u64).unwrap_or(0);
-            let model = stats.model.clone().unwrap_or_else(|| "claude-sonnet-4-5-20250929".to_string());
+            let model = stats.model.clone().unwrap_or_else(|| "claude-sonnet-4-6".to_string());
 
             (input_chars, stats.current_request_output_chars, stats.current_request_thinking_chars, stats.current_request_tools.clone(), model)
         };
 
         tracing::info!("[COST ESTIMATION] Estimating cost for interrupted request");
 
-        // Use conservative 3.5 chars/token for estimation (vs standard 4)
+        // Char-based estimation: 3.5 chars/token is intentionally conservative (standard English
+        // averages ~4 chars/token). CLI v2.1.75 fixed over-counting in Claude Code's compaction
+        // logic but does not affect this heuristic — we count characters ourselves, independently
+        // of Claude Code's internal token tracking. The 1.2 safety margin avoids undercharging.
         let estimated_input_tokens = (input_chars as f64 / 3.5).ceil() as u64;
         let estimated_output_tokens = ((output_chars as f64 / 3.5).ceil() as u64)
             + ((thinking_chars as f64 / 3.5).ceil() as u64);
@@ -1051,11 +1074,21 @@ fn handle_stderr(
                 // Hook events are informational — emit with distinct types instead of error
                 let is_worktree_create = line.contains("[WorktreeCreate Hook]");
                 let is_worktree_remove = line.contains("[WorktreeRemove Hook]");
+                let is_elicitation = line.contains("[Elicitation Hook]");
+                let is_elicitation_result = line.contains("[ElicitationResult Hook]");
+                let is_stop_failure = line.contains("[StopFailure Hook]");
+                let is_post_compact = line.contains("[PostCompact Hook]");
 
                 let line_type = if is_worktree_create || is_worktree_remove {
                     "worktree"
                 } else if line.contains("[ConfigChange Hook]") {
                     "config-change"
+                } else if is_elicitation || is_elicitation_result {
+                    "elicitation"
+                } else if is_stop_failure {
+                    "error"
+                } else if is_post_compact {
+                    "compact-prompt"
                 } else {
                     "error"
                 };
@@ -1097,6 +1130,103 @@ fn handle_stderr(
                             parent_tool_use_id: None,
                         },
                     );
+                } else if is_elicitation {
+                    let data = parse_elicitation_hook(&line);
+                    let friendly_content =
+                        format!("MCP server requesting input: {}", data.message);
+
+                    let _ = app.emit(
+                        "claude:elicitation",
+                        ElicitationEvent {
+                            message: data.message,
+                            server_name: data.server_name,
+                            request_id: data.request_id,
+                            conversation_id: conversation_id.clone(),
+                        },
+                    );
+
+                    let _ = app.emit(
+                        "claude:output",
+                        OutputEvent {
+                            line_type: "elicitation".to_string(),
+                            content: friendly_content,
+                            tool_name: None,
+                            conversation_id: conversation_id.clone(),
+                            cost: None,
+                            parent_tool_use_id: None,
+                        },
+                    );
+                } else if is_elicitation_result {
+                    let data = parse_elicitation_result_hook(&line);
+                    let friendly_content =
+                        format!("MCP elicitation completed: {}", data.action);
+
+                    let _ = app.emit(
+                        "claude:elicitation-result",
+                        ElicitationResultEvent {
+                            action: data.action,
+                            request_id: data.request_id,
+                            conversation_id: conversation_id.clone(),
+                        },
+                    );
+
+                    let _ = app.emit(
+                        "claude:output",
+                        OutputEvent {
+                            line_type: "elicitation".to_string(),
+                            content: friendly_content,
+                            tool_name: None,
+                            conversation_id: conversation_id.clone(),
+                            cost: None,
+                            parent_tool_use_id: None,
+                        },
+                    );
+                } else if is_stop_failure {
+                    let data = parse_stop_failure_hook(&line);
+                    let friendly_content = build_stop_failure_message(&data);
+
+                    let _ = app.emit(
+                        "claude:stop-failure",
+                        StopFailureEvent {
+                            stop_reason: data.stop_reason,
+                            error_type: data.error_type,
+                            conversation_id: conversation_id.clone(),
+                        },
+                    );
+
+                    let _ = app.emit(
+                        "claude:output",
+                        OutputEvent {
+                            line_type: "error".to_string(),
+                            content: friendly_content,
+                            tool_name: None,
+                            conversation_id: conversation_id.clone(),
+                            cost: None,
+                            parent_tool_use_id: None,
+                        },
+                    );
+                } else if is_post_compact {
+                    let data = parse_post_compact_hook(&line);
+
+                    let _ = app.emit(
+                        "claude:post-compact",
+                        PostCompactEvent {
+                            session_id: data.session_id,
+                            conversation_id: conversation_id.clone(),
+                        },
+                    );
+
+                    let _ = app.emit(
+                        "claude:output",
+                        OutputEvent {
+                            line_type: "compact-prompt".to_string(),
+                            content: "Context compacted — conversation history has been summarised to free up space.".to_string(),
+                            tool_name: None,
+                            conversation_id: conversation_id.clone(),
+                            cost: None,
+                            parent_tool_use_id: None,
+                        },
+                    );
                 } else {
                     let _ = app.emit(
                         "claude:output",
@@ -1235,6 +1365,111 @@ fn parse_subagent_stop_hook(line: &str) -> Option<SubagentStopData> {
     })
 }
 
+#[derive(Debug)]
+struct ElicitationData {
+    message: String,
+    server_name: Option<String>,
+    request_id: Option<String>,
+}
+
+fn parse_elicitation_hook(line: &str) -> ElicitationData {
+    let message = extract_quoted_value(line, "message").unwrap_or_else(|| {
+        line.split("[Elicitation Hook]")
+            .nth(1)
+            .unwrap_or("")
+            .trim()
+            .to_string()
+    });
+
+    let server_name = extract_debug_string_value(line, "server_name");
+    let request_id = extract_debug_string_value(line, "request_id");
+
+    ElicitationData { message, server_name, request_id }
+}
+
+#[derive(Debug)]
+struct ElicitationResultData {
+    action: String,
+    request_id: Option<String>,
+}
+
+fn parse_elicitation_result_hook(line: &str) -> ElicitationResultData {
+    let action =
+        extract_quoted_value(line, "action").unwrap_or_else(|| "unknown".to_string());
+
+    let request_id = extract_debug_string_value(line, "request_id");
+
+    ElicitationResultData { action, request_id }
+}
+
+#[derive(Debug)]
+struct StopFailureData {
+    stop_reason: Option<String>,
+    error_type: Option<String>,
+}
+
+fn parse_stop_failure_hook(line: &str) -> StopFailureData {
+    let stop_reason = extract_quoted_value(line, "stop_reason");
+    let error_type = extract_debug_string_value(line, "error_type");
+
+    StopFailureData { stop_reason, error_type }
+}
+
+/// Builds a user-friendly message from a `StopFailureData` instance.
+fn build_stop_failure_message(data: &StopFailureData) -> String {
+    match data.stop_reason.as_deref() {
+        Some("rate_limit") => "Session stopped: rate limit reached".to_string(),
+        Some("auth_failure") | Some("authentication") => {
+            "Session stopped: authentication failed".to_string()
+        }
+        Some(reason) => format!("Session stopped due to API error: {}", reason),
+        None => match data.error_type.as_deref() {
+            Some(et) => format!("Session stopped due to API error: {}", et),
+            None => "Session stopped due to an unknown API error".to_string(),
+        },
+    }
+}
+
+#[derive(Debug)]
+struct PostCompactData {
+    session_id: Option<String>,
+}
+
+fn parse_post_compact_hook(line: &str) -> PostCompactData {
+    let session_id = extract_debug_string_value(line, "session_id");
+    PostCompactData { session_id }
+}
+
+/// Extracts a double-quoted string value from a `key="value"` pair in a hook line.
+/// Handles escape sequences within the quoted value.
+fn extract_quoted_value(line: &str, key: &str) -> Option<String> {
+    let prefix = format!("{}=\"", key);
+    let start_idx = line.find(&prefix)? + prefix.len();
+    let rest = &line[start_idx..];
+
+    let mut result = String::new();
+    let mut chars = rest.chars();
+    loop {
+        match chars.next() {
+            Some('"') => return Some(result),
+            Some('\\') => match chars.next() {
+                Some('n') => result.push('\n'),
+                Some('t') => result.push('\t'),
+                Some('"') => result.push('"'),
+                Some('\\') => result.push('\\'),
+                Some(c) => {
+                    result.push('\\');
+                    result.push(c);
+                }
+                None => break,
+            },
+            Some(c) => result.push(c),
+            None => break,
+        }
+    }
+    None
+}
+
 /// Extract text content from a ToolResult's `content` field.
 /// The content may be a JSON string or an array of typed content blocks.
 fn extract_tool_result_text(content: &serde_json::Value) -> Option<String> {
@@ -1356,7 +1591,7 @@ fn process_json_line(
                     stats_guard.model.clone()
                 }).unwrap_or_else(|| {
                     tracing::warn!("No model info available for cost calculation, using default");
-                    "claude-sonnet-4-5-20250929".to_string()
+                    "claude-sonnet-4-6".to_string()
                 });
 
                 // Calculate cost for historical tracking (including cache tokens)
@@ -3191,4 +3426,218 @@ mod tests {
         let result = build_combined_settings_arg(Some(""), None);
         assert_eq!(result, "{}");
     }
+
+    #[test]
+    fn test_extract_quoted_value_basic() {
+        let line = r#"[Elicitation Hook] message="Hello world", server_name=Some("srv")"#;
+        let result = extract_quoted_value(line, "message");
+        assert_eq!(result, Some("Hello world".to_string()));
+    }
+
+    #[test]
+    fn test_extract_quoted_value_with_escapes() {
+        let line = r#"[Elicitation Hook] message="Line one\nLine two", request_id=Some("r1")"#;
+        let result = extract_quoted_value(line, "message");
+        assert_eq!(result, Some("Line one\nLine two".to_string()));
+    }
+
+    #[test]
+    fn test_extract_quoted_value_missing() {
+        let line = r#"[Elicitation Hook] server_name=Some("srv")"#;
+        let result = extract_quoted_value(line, "message");
+        assert_eq!(result, None);
+    }
+
+    #[test]
+    fn test_parse_elicitation_hook_with_all_fields() {
+        let line = r#"[Elicitation Hook] message="Please enter your API key", server_name=Some("my-mcp"), request_id=Some("req-456")"#;
+        let data = parse_elicitation_hook(line);
+        assert_eq!(data.message, "Please enter your API key");
+        assert_eq!(data.server_name, Some("my-mcp".to_string()));
+        assert_eq!(data.request_id, Some("req-456".to_string()));
+    }
+
+    #[test]
+    fn test_parse_elicitation_hook_missing_optional_fields() {
+        let line = r#"[Elicitation Hook] message="What is the endpoint?", server_name=None, request_id=None"#;
+        let data = parse_elicitation_hook(line);
+        assert_eq!(data.message, "What is the endpoint?");
+        assert_eq!(data.server_name, None);
+        assert_eq!(data.request_id, None);
+    }
+
+    #[test]
+    fn test_parse_elicitation_hook_invalid_line() {
+        let line = "[Elicitation Hook] some unstructured data";
+        let data = parse_elicitation_hook(line);
+        assert_eq!(data.message, "some unstructured data");
+        assert_eq!(data.server_name, None);
+        assert_eq!(data.request_id, None);
+    }
+
+    #[test]
+    fn test_parse_elicitation_result_hook_accept() {
+        let line = r#"[ElicitationResult Hook] action="accept", request_id=Some("req-789")"#;
+        let data = parse_elicitation_result_hook(line);
+        assert_eq!(data.action, "accept");
+        assert_eq!(data.request_id, Some("req-789".to_string()));
+    }
+
+    #[test]
+    fn test_parse_elicitation_result_hook_cancel() {
+        let line = r#"[ElicitationResult Hook] action="cancel", request_id=None"#;
+        let data = parse_elicitation_result_hook(line);
+        assert_eq!(data.action, "cancel");
+        assert_eq!(data.request_id, None);
+    }
+
+    #[test]
+    fn test_parse_stop_failure_hook_with_all_fields() {
+        let line = r#"[StopFailure Hook] stop_reason="api_error", error_type=Some("rate_limit"), conversation_id=Some("conv-123")"#;
+        let data = parse_stop_failure_hook(line);
+        assert_eq!(data.stop_reason, Some("api_error".to_string()));
+        assert_eq!(data.error_type, Some("rate_limit".to_string()));
+    }
+
+    #[test]
+    fn test_parse_stop_failure_hook_missing_optional_error_type() {
+        let line = r#"[StopFailure Hook] stop_reason="api_error", error_type=None"#;
+        let data = parse_stop_failure_hook(line);
+        assert_eq!(data.stop_reason, Some("api_error".to_string()));
+        assert_eq!(data.error_type, None);
+    }
+
+    #[test]
+    fn test_parse_stop_failure_hook_invalid_line() {
+        let line = "[StopFailure Hook] some unstructured data";
+        let data = parse_stop_failure_hook(line);
+        assert_eq!(data.stop_reason, None);
+        assert_eq!(data.error_type, None);
+    }
+
+    #[test]
+    fn test_build_stop_failure_message_rate_limit() {
+        let data = StopFailureData {
+            stop_reason: Some("rate_limit".to_string()),
+            error_type: None,
+        };
+        assert_eq!(build_stop_failure_message(&data), "Session stopped: rate limit reached");
+    }
+
+    #[test]
+    fn test_build_stop_failure_message_auth_failure() {
+        let data = StopFailureData {
+            stop_reason: Some("auth_failure".to_string()),
+            error_type: None,
+        };
+        assert_eq!(build_stop_failure_message(&data), "Session stopped: authentication failed");
+    }
+
+    #[test]
+    fn test_build_stop_failure_message_authentication() {
+        let data = StopFailureData {
+            stop_reason: Some("authentication".to_string()),
+            error_type: None,
+        };
+        assert_eq!(build_stop_failure_message(&data), "Session stopped: authentication failed");
+    }
+
+    #[test]
+    fn test_build_stop_failure_message_unknown_reason() {
+        let data = StopFailureData {
+            stop_reason: Some("server_error".to_string()),
+            error_type: None,
+        };
+        assert_eq!(
+            build_stop_failure_message(&data),
+            "Session stopped due to API error: server_error"
+        );
+    }
+
+    #[test]
+    fn test_build_stop_failure_message_no_reason_with_error_type() {
+        let data = StopFailureData {
+            stop_reason: None,
+            error_type: Some("timeout".to_string()),
+        };
+        assert_eq!(
+            build_stop_failure_message(&data),
+            "Session stopped due to API error: timeout"
+        );
+    }
+
+    #[test]
+    fn test_parse_post_compact_hook_with_session_id() {
+        let line =
+            r#"[PostCompact Hook] session_id=Some("sess-abc123"), conversation_id=Some("conv-xyz")"#;
+        let data = parse_post_compact_hook(line);
+        assert_eq!(data.session_id, Some("sess-abc123".to_string()));
+    }
+
+    #[test]
+    fn test_parse_post_compact_hook_without_session_id() {
+        let line = "[PostCompact Hook] session_id=None";
+        let data = parse_post_compact_hook(line);
+        assert_eq!(data.session_id, None);
+    }
+
+    #[test]
+    fn test_parse_post_compact_hook_empty_line() {
+        let line = "[PostCompact Hook]";
+        let data = parse_post_compact_hook(line);
+        assert_eq!(data.session_id, None);
+    }
+
+    #[test]
+    fn test_build_stop_failure_message_no_fields() {
+        let data = StopFailureData {
+            stop_reason: None,
+            error_type: None,
+        };
+        assert_eq!(
+            build_stop_failure_message(&data),
+            "Session stopped due to an unknown API error"
+        );
+    }
+
+    /// Build the --name argument string without executing a command (for testing)
+    #[cfg(test)]
+    fn build_session_name_arg(name: &str) -> Option<(String, String)> {
+        if name.is_empty() {
+            return None;
+        }
+        Some(("--name".to_string(), name.to_string()))
+    }
+
+    #[test]
+    fn test_e2e_session_name_passed_when_set() {
+        let name = "Sakura";
+        let result = build_session_name_arg(name);
+        assert!(result.is_some());
+        let (flag, value) = result.unwrap();
+        assert_eq!(flag, "--name");
+        assert_eq!(value, "Sakura");
+    }
+
+    #[test]
+    fn test_e2e_session_name_not_passed_when_none() {
+        let options = ClaudeStartOptions {
+            session_name: None,
+            ..Default::default()
+        };
+        // When session_name is None, no --name arg should be produced
+        let has_name = options.session_name.as_deref().map(|n| !n.is_empty()).unwrap_or(false);
+        assert!(!has_name);
+    }
+
+    #[test]
+    fn test_e2e_session_name_not_passed_when_empty() {
+        let options = ClaudeStartOptions {
+            session_name: Some(String::new()),
+            ..Default::default()
+        };
+        // When session_name is Some(""), no --name arg should be produced
+        let has_name = options.session_name.as_deref().map(|n| !n.is_empty()).unwrap_or(false);
+        assert!(!has_name);
+    }
 }
diff --git a/src/lib/commands/slashCommands.ts b/src/lib/commands/slashCommands.ts
index 78f1a10..d19e871 100644
--- a/src/lib/commands/slashCommands.ts
+++ b/src/lib/commands/slashCommands.ts
@@ -71,6 +71,7 @@ async function changeDirectory(path: string): Promise<void> {
         enable_claudeai_mcp_servers: config.enable_claudeai_mcp_servers ?? true,
         auto_memory_directory: config.auto_memory_directory || null,
         model_overrides: config.model_overrides || null,
+        session_name: null,
       },
     });
 
@@ -152,6 +153,7 @@ async function startNewConversation(): Promise<void> {
         enable_claudeai_mcp_servers: config.enable_claudeai_mcp_servers ?? true,
         auto_memory_directory: config.auto_memory_directory || null,
         model_overrides: config.model_overrides || null,
+        session_name: null,
       },
     });
 
diff --git a/src/lib/components/CliVersion.svelte b/src/lib/components/CliVersion.svelte
index 2361492..b48166f 100644
--- a/src/lib/components/CliVersion.svelte
+++ b/src/lib/components/CliVersion.svelte
@@ -2,7 +2,7 @@
   import { invoke } from "@tauri-apps/api/core";
   import { onMount } from "svelte";
 
-  const SUPPORTED_CLI_VERSION = "2.1.74";
+  const SUPPORTED_CLI_VERSION = "2.1.80";
 
   let installedVersion = $state("Loading...");
   let latestNpmVersion = $state<string | null>(null);
diff --git a/src/lib/components/ConfigSidebar.svelte b/src/lib/components/ConfigSidebar.svelte
index e7b17d2..0a26a2b 100644
--- a/src/lib/components/ConfigSidebar.svelte
+++ b/src/lib/components/ConfigSidebar.svelte
@@ -610,13 +610,15 @@
           id="max-output-tokens"
           type="number"
           min="1"
-          placeholder="Default (32000)"
+          max="128000"
+          placeholder="Default (model-dependent)"
           bind:value={config.max_output_tokens}
           class="w-full px-3 py-2 text-sm bg-[var(--bg-primary)] border border-[var(--border-color)] rounded text-[var(--text-primary)] placeholder-[var(--text-tertiary)] focus:outline-none focus:border-[var(--accent-primary)]"
         />
         <p class="text-xs text-[var(--text-tertiary)] mt-1">
-          Sets <code class="font-mono">CLAUDE_CODE_MAX_OUTPUT_TOKENS</code> — increase if responses are
-          being cut off mid-reply
+          Sets <code class="font-mono">CLAUDE_CODE_MAX_OUTPUT_TOKENS</code>. Maximum: 128k tokens
+          for Opus 4.6 and Sonnet 4.6 (64k default for Opus 4.6, 32k for other models). Increase if
+          responses are being cut off.
         </p>
       </div>
 
diff --git a/src/lib/components/ElicitationModal.svelte b/src/lib/components/ElicitationModal.svelte
new file mode 100644
index 0000000..0b3a4ca
--- /dev/null
+++ b/src/lib/components/ElicitationModal.svelte
@@ -0,0 +1,188 @@
+<script lang="ts">
+  import { invoke } from "@tauri-apps/api/core";
+  import { get } from "svelte/store";
+  import { claudeStore, hasElicitationPending } from "$lib/stores/claude";
+  import { characterState } from "$lib/stores/character";
+  import type { ElicitationEvent } from "$lib/types/messages";
+  import { updateDiscordRpc, setSkipNextGreeting } from "$lib/tauri";
+  import { conversationsStore } from "$lib/stores/conversations";
+  import { configStore } from "$lib/stores/config";
+
+  let isVisible = $state(false);
+  let elicitation: ElicitationEvent | null = $state(null);
+  let response = $state("");
+  let grantedToolsList: string[] = $state([]);
+  let workingDirectory = $state("");
+
+  hasElicitationPending.subscribe((pending) => {
+    isVisible = pending;
+    if (!pending) {
+      response = "";
+    }
+  });
+
+  claudeStore.pendingElicitation.subscribe((e) => {
+    elicitation = e;
+    if (e) {
+      characterState.setState("permission");
+    }
+  });
+
+  claudeStore.grantedTools.subscribe((tools) => {
+    grantedToolsList = Array.from(tools);
+  });
+
+  claudeStore.currentWorkingDirectory.subscribe((dir) => {
+    workingDirectory = dir;
+  });
+
+  async function handleSubmitAndReconnect() {
+    if (!elicitation || !response.trim()) return;
+
+    const conversationId = get(claudeStore.activeConversationId);
+    if (!conversationId) return;
+
+    const responseText = response.trim();
+    const elicitationMessage = elicitation.message;
+    const conversationHistory = claudeStore.getConversationHistory();
+
+    claudeStore.addLine("system", `MCP response submitted. Reconnecting with context...`);
+    claudeStore.clearElicitation();
+
+    try {
+      setSkipNextGreeting(true);
+
+      await invoke("stop_claude", { conversationId });
+
+      await new Promise((resolve) => setTimeout(resolve, 500));
+
+      const config = configStore.getConfig();
+      await invoke("start_claude", {
+        conversationId,
+        options: {
+          working_dir: workingDirectory || "/home/naomi",
+          model: config.model || null,
+          api_key: config.api_key || null,
+          custom_instructions: config.custom_instructions || null,
+          mcp_servers_json: config.mcp_servers_json || null,
+          allowed_tools: grantedToolsList,
+          use_worktree: config.use_worktree ?? false,
+          disable_1m_context: config.disable_1m_context ?? false,
+          include_git_instructions: config.include_git_instructions ?? true,
+          enable_claudeai_mcp_servers: config.enable_claudeai_mcp_servers ?? true,
+          auto_memory_directory: config.auto_memory_directory || null,
+          model_overrides: config.model_overrides || null,
+          session_name: null,
+        },
+      });
+
+      const activeConversation = get(conversationsStore.activeConversation);
+      if (activeConversation) {
+        await updateDiscordRpc(
+          activeConversation.name,
+          config.model || "claude",
+          activeConversation.startedAt
+        );
+      }
+
+      await new Promise((resolve) => setTimeout(resolve, 1000));
+
+      if (conversationHistory) {
+        const contextMessage = `[CONTEXT RESTORATION]
+I just responded to an MCP server elicitation request. Here's our conversation so far:
+
+${conversationHistory}
+
+The MCP server asked: "${elicitationMessage}"
+My response: "${responseText}"
+
+Please continue where we left off, taking my response into account.`;
+
+        await invoke("send_prompt", {
+          conversationId,
+          message: contextMessage,
+        });
+      }
+
+      characterState.setTemporaryState("success", 2000);
+    } catch (error) {
+      console.error("Failed to reconnect:", error);
+      claudeStore.addLine("error", `Reconnect failed: ${error}`);
+      characterState.setTemporaryState("error", 3000);
+    }
+  }
+
+  function handleDismiss() {
+    claudeStore.clearElicitation();
+    claudeStore.addLine("system", "MCP elicitation dismissed");
+    characterState.setTemporaryState("idle", 1000);
+  }
+
+  function handleKeydown(event: KeyboardEvent) {
+    if (!isVisible || !elicitation) return;
+
+    if (event.key === "Escape") {
+      event.preventDefault();
+      handleDismiss();
+    }
+  }
+
+  function canSubmit(): boolean {
+    return response.trim().length > 0;
+  }
+</script>
+
+<svelte:window onkeydown={handleKeydown} />
+
+{#if isVisible && elicitation}
+  <div
+    class="elicitation-overlay fixed inset-0 bg-black/70 flex items-center justify-center z-50 backdrop-blur-sm"
+  >
+    <div
+      class="elicitation-modal bg-[var(--bg-primary)] border border-[var(--border-color)] rounded-xl p-6 max-w-md w-full mx-4 shadow-2xl"
+    >
+      <div class="flex items-center gap-3 mb-4">
+        <div class="w-10 h-10 rounded-full bg-blue-500/20 flex items-center justify-center">
+          <span class="text-xl">💬</span>
+        </div>
+        <div>
+          <h2 class="text-lg font-semibold text-[var(--text-primary)]">MCP Server Request</h2>
+          {#if elicitation.server_name}
+            <p class="text-sm text-[var(--text-secondary)]">from: {elicitation.server_name}</p>
+          {:else}
+            <p class="text-sm text-[var(--text-secondary)]">Input required from MCP server</p>
+          {/if}
+        </div>
+      </div>
+
+      <div class="mb-4">
+        <p class="text-[var(--text-primary)]">{elicitation.message}</p>
+      </div>
+
+      <div class="mb-4">
+        <textarea
+          bind:value={response}
+          placeholder="Type your response here..."
+          class="w-full px-4 py-3 bg-[var(--bg-secondary)] border border-[var(--border-color)] rounded-lg text-[var(--text-primary)] placeholder-[var(--text-secondary)] resize-none focus:outline-none focus:border-[var(--accent-primary)]"
+          rows="4"
+        ></textarea>
+      </div>
+
+      <div class="flex gap-3">
+        <button
+          onclick={handleDismiss}
+          class="flex-1 px-4 py-2 bg-gray-500/20 hover:bg-gray-500/30 text-[var(--text-secondary)] rounded-lg transition-colors font-medium"
+        >
+          Dismiss
+        </button>
+        <button
+          onclick={handleSubmitAndReconnect}
+          disabled={!canSubmit()}
+          class="flex-1 px-4 py-2 bg-blue-500/20 hover:bg-blue-500/30 text-blue-400 rounded-lg transition-colors font-medium disabled:opacity-50 disabled:cursor-not-allowed"
+        >
+          Submit & Reconnect
+        </button>
+      </div>
+    </div>
+  </div>
+{/if}
diff --git a/src/lib/components/InputBar.svelte b/src/lib/components/InputBar.svelte
index fbb799f..718ebc2 100644
--- a/src/lib/components/InputBar.svelte
+++ b/src/lib/components/InputBar.svelte
@@ -406,6 +406,7 @@ User: ${formattedMessage}`;
               enable_claudeai_mcp_servers: config.enable_claudeai_mcp_servers ?? true,
               auto_memory_directory: config.auto_memory_directory || null,
               model_overrides: config.model_overrides || null,
+              session_name: null,
             },
           });
 
diff --git a/src/lib/components/MemoryBrowserPanel.svelte b/src/lib/components/MemoryBrowserPanel.svelte
index 72d1bb3..b9088fc 100644
--- a/src/lib/components/MemoryBrowserPanel.svelte
+++ b/src/lib/components/MemoryBrowserPanel.svelte
@@ -14,6 +14,7 @@
   interface MemoryFileInfo {
     path: string;
     heading: string | null;
+    last_modified?: string; // Unix timestamp in seconds as a string, optional for backwards compat
   }
 
   interface MemoryFilesResponse {
@@ -65,6 +66,16 @@
     return file.heading ?? getFileName(file.path);
   }
 
+  function formatLastModified(ts: string | undefined): string {
+    if (!ts) return "";
+    const date = new Date(Number(ts) * 1000);
+    return date.toLocaleDateString(undefined, {
+      year: "numeric",
+      month: "short",
+      day: "numeric",
+    });
+  }
+
   async function sendMemoryCommand() {
     const conversationId = get(claudeStore.activeConversationId);
     if (!conversationId) return;
@@ -205,7 +216,12 @@
                     d="M9 12h6m-6 4h6m2 5H7a2 2 0 01-2-2V5a2 2 0 012-2h5.586a1 1 0 01.707.293l5.414 5.414a1 1 0 01.293.707V19a2 2 0 01-2 2z"
                   />
                 </svg>
-                <span class="file-name">{getDisplayName(file)}</span>
+                <div class="file-info">
+                  <span class="file-name">{getDisplayName(file)}</span>
+                  {#if file.last_modified}
+                    <span class="file-date">{formatLastModified(file.last_modified)}</span>
+                  {/if}
+                </div>
               </button>
             {/each}
           </div>
@@ -416,7 +432,7 @@
 
   .file-item {
     display: flex;
-    align-items: center;
+    align-items: flex-start;
     gap: 0.75rem;
     padding: 0.75rem 1rem;
     background: var(--bg-secondary);
@@ -445,6 +461,13 @@
     flex-shrink: 0;
   }
 
+  .file-info {
+    display: flex;
+    flex-direction: column;
+    gap: 0.125rem;
+    overflow: hidden;
+  }
+
   .file-name {
     font-size: 0.875rem;
     font-weight: 500;
@@ -453,6 +476,15 @@
     white-space: nowrap;
   }
 
+  .file-date {
+    font-size: 0.75rem;
+    color: var(--text-secondary);
+  }
+
+  .file-item.active .file-date {
+    color: rgba(255, 255, 255, 0.75);
+  }
+
   .file-viewer {
     display: flex;
     flex-direction: column;
diff --git a/src/lib/components/PermissionModal.svelte b/src/lib/components/PermissionModal.svelte
index f4035f3..9f8f7e1 100644
--- a/src/lib/components/PermissionModal.svelte
+++ b/src/lib/components/PermissionModal.svelte
@@ -93,6 +93,7 @@
           enable_claudeai_mcp_servers: config.enable_claudeai_mcp_servers ?? true,
           auto_memory_directory: config.auto_memory_directory || null,
           model_overrides: config.model_overrides || null,
+          session_name: null,
         },
       });
 
diff --git a/src/lib/components/StatusBar.svelte b/src/lib/components/StatusBar.svelte
index 9b69a63..a4d9887 100644
--- a/src/lib/components/StatusBar.svelte
+++ b/src/lib/components/StatusBar.svelte
@@ -160,6 +160,7 @@
       if (!conversationId) {
         throw new Error("No active conversation");
       }
+      const activeConversationForName = get(conversationsStore.activeConversation);
       await invoke("start_claude", {
         conversationId,
         options: {
@@ -177,6 +178,7 @@
           enable_claudeai_mcp_servers: currentConfig.enable_claudeai_mcp_servers ?? true,
           auto_memory_directory: currentConfig.auto_memory_directory || null,
           model_overrides: currentConfig.model_overrides || null,
+          session_name: activeConversationForName?.name || null,
         },
       });
 
@@ -338,6 +340,7 @@
           enable_claudeai_mcp_servers: currentConfig.enable_claudeai_mcp_servers ?? true,
           auto_memory_directory: currentConfig.auto_memory_directory || null,
           model_overrides: currentConfig.model_overrides || null,
+          session_name: null,
         },
       });
 
diff --git a/src/lib/components/TaskLoopPanel.svelte b/src/lib/components/TaskLoopPanel.svelte
index cacd72a..82daaba 100644
--- a/src/lib/components/TaskLoopPanel.svelte
+++ b/src/lib/components/TaskLoopPanel.svelte
@@ -222,6 +222,7 @@
           enable_claudeai_mcp_servers: cfg.enable_claudeai_mcp_servers ?? true,
           auto_memory_directory: cfg.auto_memory_directory || null,
           model_overrides: cfg.model_overrides || null,
+          session_name: null,
         },
       });
     } catch (error) {
diff --git a/src/lib/components/UserQuestionModal.svelte b/src/lib/components/UserQuestionModal.svelte
index bcaf500..e887b7f 100644
--- a/src/lib/components/UserQuestionModal.svelte
+++ b/src/lib/components/UserQuestionModal.svelte
@@ -112,6 +112,7 @@
           enable_claudeai_mcp_servers: config.enable_claudeai_mcp_servers ?? true,
           auto_memory_directory: config.auto_memory_directory || null,
           model_overrides: config.model_overrides || null,
+          session_name: null,
         },
       });
 
diff --git a/src/lib/stores/claude.ts b/src/lib/stores/claude.ts
index 3b3cdcb..246e8b5 100644
--- a/src/lib/stores/claude.ts
+++ b/src/lib/stores/claude.ts
@@ -22,6 +22,7 @@ export const claudeStore = {
   terminalLines: conversationsStore.terminalLines,
   pendingPermission: conversationsStore.pendingPermission,
   pendingQuestion: conversationsStore.pendingQuestion,
+  pendingElicitation: conversationsStore.pendingElicitation,
   isProcessing: conversationsStore.isProcessing,
   grantedTools: conversationsStore.grantedTools,
   pendingRetryMessage: conversationsStore.pendingRetryMessage,
@@ -57,6 +58,10 @@ export const claudeStore = {
   clearQuestion: conversationsStore.clearQuestion,
   requestQuestionForConversation: conversationsStore.requestQuestionForConversation,
   clearQuestionForConversation: conversationsStore.clearQuestionForConversation,
+  requestElicitation: conversationsStore.requestElicitation,
+  clearElicitation: conversationsStore.clearElicitation,
+  requestElicitationForConversation: conversationsStore.requestElicitationForConversation,
+  clearElicitationForConversation: conversationsStore.clearElicitationForConversation,
   grantTool: conversationsStore.grantTool,
   revokeAllTools: conversationsStore.revokeAllTools,
   isToolGranted: conversationsStore.isToolGranted,
@@ -126,6 +131,12 @@ export const hasQuestionPending = derived(
   ($conversation) => $conversation?.pendingQuestion !== null
 );
 
+export const hasElicitationPending = derived(
+  claudeStore.activeConversation,
+  ($conversation) =>
+    $conversation?.pendingElicitation !== null && $conversation?.pendingElicitation !== undefined
+);
+
 // Derived store to check if Claude is currently processing (can be interrupted)
 export const isClaudeProcessing = derived(
   [claudeStore.connectionStatus, characterState],
diff --git a/src/lib/stores/conversations.ts b/src/lib/stores/conversations.ts
index cf8bf31..f34615a 100644
--- a/src/lib/stores/conversations.ts
+++ b/src/lib/stores/conversations.ts
@@ -2,6 +2,7 @@ import { writable, derived, get } from "svelte/store";
 import type {
   TerminalLine,
   ConnectionStatus,
+  ElicitationEvent,
   PermissionRequest,
   UserQuestionEvent,
   Attachment,
@@ -32,6 +33,7 @@ export interface Conversation {
   grantedTools: Set<string>;
   pendingPermissions: PermissionRequest[];
   pendingQuestion: UserQuestionEvent | null;
+  pendingElicitation: ElicitationEvent | null;
   scrollPosition: number;
   createdAt: Date;
   lastActivityAt: Date;
@@ -157,6 +159,7 @@ function createConversationsStore() {
       grantedTools: new Set(),
       pendingPermissions: [],
       pendingQuestion: null,
+      pendingElicitation: null,
       scrollPosition: -1, // -1 means "scroll to bottom" (auto-scroll)
       createdAt: new Date(),
       lastActivityAt: new Date(),
@@ -221,6 +224,10 @@ function createConversationsStore() {
     ($conv) => $conv?.pendingPermissions || []
   );
   const pendingQuestion = derived(activeConversation, ($conv) => $conv?.pendingQuestion || null);
+  const pendingElicitation = derived(
+    activeConversation,
+    ($conv) => $conv?.pendingElicitation ?? null
+  );
   const scrollPosition = derived(activeConversation, ($conv) => $conv?.scrollPosition ?? -1);
   const attachments = derived(activeConversation, ($conv) => $conv?.attachments || []);
   const worktreeInfo = derived(activeConversation, ($conv) => $conv?.worktreeInfo ?? null);
@@ -234,6 +241,7 @@ function createConversationsStore() {
     pendingPermission: { subscribe: pendingPermission.subscribe },
     pendingPermissions: { subscribe: pendingPermissions.subscribe },
     pendingQuestion: { subscribe: pendingQuestion.subscribe },
+    pendingElicitation: { subscribe: pendingElicitation.subscribe },
     isProcessing: { subscribe: isProcessing.subscribe },
     grantedTools: { subscribe: grantedTools.subscribe },
     pendingRetryMessage: { subscribe: pendingRetryMessage.subscribe },
@@ -399,6 +407,52 @@ function createConversationsStore() {
         return convs;
       });
     },
+    requestElicitation: (elicitation: ElicitationEvent) => {
+      const activeId = get(activeConversationId);
+      if (!activeId) return;
+
+      conversations.update((convs) => {
+        const conv = convs.get(activeId);
+        if (conv) {
+          conv.pendingElicitation = elicitation;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
+    clearElicitation: () => {
+      const activeId = get(activeConversationId);
+      if (!activeId) return;
+
+      conversations.update((convs) => {
+        const conv = convs.get(activeId);
+        if (conv) {
+          conv.pendingElicitation = null;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
+    requestElicitationForConversation: (conversationId: string, elicitation: ElicitationEvent) => {
+      conversations.update((convs) => {
+        const conv = convs.get(conversationId);
+        if (conv) {
+          conv.pendingElicitation = elicitation;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
+    clearElicitationForConversation: (conversationId: string) => {
+      conversations.update((convs) => {
+        const conv = convs.get(conversationId);
+        if (conv) {
+          conv.pendingElicitation = null;
+          conv.lastActivityAt = new Date();
+        }
+        return convs;
+      });
+    },
     setPendingRetryMessage: (message: string | null) => pendingRetryMessage.set(message),
 
     // Conversation management
diff --git a/src/lib/stores/toasts.test.ts b/src/lib/stores/toasts.test.ts
index 113baed..0066e37 100644
--- a/src/lib/stores/toasts.test.ts
+++ b/src/lib/stores/toasts.test.ts
@@ -187,6 +187,33 @@ describe("toastStore", () => {
     });
   });
 
+  describe("addError", () => {
+    it("adds an error toast with the warning icon", () => {
+      toastStore.addError("Something went wrong");
+      const toasts = get(toastStore);
+      expect(toasts).toHaveLength(1);
+      const toast = toasts[0];
+      expect(toast.kind).toBe("info");
+      if (toast.kind === "info") {
+        expect(toast.message).toBe("Something went wrong");
+        expect(toast.icon).toBe("⚠️");
+        expect(typeof toast.id).toBe("string");
+        expect(toast.id.length).toBeGreaterThan(0);
+      }
+    });
+
+    it("auto-dismisses after 6000ms", () => {
+      toastStore.addError("Rate limit reached");
+      expect(get(toastStore)).toHaveLength(1);
+
+      vi.advanceTimersByTime(5999);
+      expect(get(toastStore)).toHaveLength(1);
+
+      vi.advanceTimersByTime(1);
+      expect(get(toastStore)).toHaveLength(0);
+    });
+  });
+
   describe("addUpdate", () => {
     it("adds a persistent update toast with the correct fields", () => {
       toastStore.addUpdate("2.0.0", "1.9.0", "https://example.com/release");
diff --git a/src/lib/stores/toasts.ts b/src/lib/stores/toasts.ts
index 897d357..423b518 100644
--- a/src/lib/stores/toasts.ts
+++ b/src/lib/stores/toasts.ts
@@ -68,6 +68,13 @@ function createToastStore() {
     setTimeout(() => remove(id), 4000);
   }
 
+  function addError(message: string) {
+    const id = crypto.randomUUID();
+    const toast: InfoToast = { id, kind: "info", message, icon: "⚠️" };
+    update((toasts) => [...toasts, toast]);
+    setTimeout(() => remove(id), 6000);
+  }
+
   function addAchievement(achievement: AchievementUnlockedEvent["achievement"]) {
     const id = crypto.randomUUID();
     const toast: AchievementToast = { id, kind: "achievement", achievement };
@@ -82,7 +89,7 @@ function createToastStore() {
     // Update toasts are persistent — no auto-dismiss
   }
 
-  return { subscribe, addInfo, addAchievement, addUpdate, remove };
+  return { subscribe, addInfo, addError, addAchievement, addUpdate, remove };
 }
 
 export const toastStore = createToastStore();
diff --git a/src/lib/tauri.ts b/src/lib/tauri.ts
index c1e5252..ac33c02 100644
--- a/src/lib/tauri.ts
+++ b/src/lib/tauri.ts
@@ -8,7 +8,10 @@ import { initStatsListener, resetSessionStats } from "$lib/stores/stats";
 import { initAchievementsListener } from "$lib/stores/achievements";
 import type {
   ConnectionStatus,
+  ElicitationEvent,
   PermissionPromptEvent,
+  PostCompactEvent,
+  StopFailureEvent,
   UserQuestionEvent,
 } from "$lib/types/messages";
 import type { CharacterState } from "$lib/types/states";
@@ -406,7 +409,8 @@ export async function initializeTauriListeners() {
           | "rate-limit"
           | "compact-prompt"
           | "worktree"
-          | "config-change",
+          | "config-change"
+          | "elicitation",
         content,
         tool_name || undefined,
         costData,
@@ -425,7 +429,8 @@ export async function initializeTauriListeners() {
           | "rate-limit"
           | "compact-prompt"
           | "worktree"
-          | "config-change",
+          | "config-change"
+          | "elicitation",
         content,
         tool_name || undefined,
         costData,
@@ -611,6 +616,56 @@ export async function initializeTauriListeners() {
     }
   });
   unlisteners.push(questionUnlisten);
+
+  const elicitationUnlisten = await listen<ElicitationEvent>("claude:elicitation", (event) => {
+    const elicitationEvent = event.payload;
+    if (elicitationEvent.conversation_id) {
+      claudeStore.requestElicitationForConversation(
+        elicitationEvent.conversation_id,
+        elicitationEvent
+      );
+    } else {
+      claudeStore.requestElicitation(elicitationEvent);
+    }
+  });
+  unlisteners.push(elicitationUnlisten);
+
+  const elicitationResultUnlisten = await listen<{ conversation_id?: string }>(
+    "claude:elicitation-result",
+    (event) => {
+      const { conversation_id } = event.payload;
+      if (conversation_id) {
+        claudeStore.clearElicitationForConversation(conversation_id);
+      } else {
+        claudeStore.clearElicitation();
+      }
+    }
+  );
+  unlisteners.push(elicitationResultUnlisten);
+
+  const stopFailureUnlisten = await listen<StopFailureEvent>("claude:stop-failure", (event) => {
+    const { stop_reason, error_type } = event.payload;
+
+    characterState.setTemporaryState("error", 3000);
+
+    let message: string;
+    if (stop_reason === "rate_limit") {
+      message = "Rate limit reached";
+    } else if (stop_reason === "auth_failure" || stop_reason === "authentication") {
+      message = "Authentication failed";
+    } else {
+      message = `API error: ${stop_reason ?? error_type ?? "unknown"}`;
+    }
+
+    toastStore.addError(message);
+  });
+  unlisteners.push(stopFailureUnlisten);
+
+  const postCompactUnlisten = await listen<PostCompactEvent>("claude:post-compact", () => {
+    toastStore.addInfo("Context compacted", "🗜️");
+    characterState.setTemporaryState("success", 2000);
+  });
+  unlisteners.push(postCompactUnlisten);
 }
 
 export function cleanupTauriListeners() {
diff --git a/src/lib/types/messages.ts b/src/lib/types/messages.ts
index 966ebb1..754f94c 100644
--- a/src/lib/types/messages.ts
+++ b/src/lib/types/messages.ts
@@ -10,7 +10,8 @@ export interface TerminalLine {
     | "rate-limit"
     | "compact-prompt"
     | "worktree"
-    | "config-change";
+    | "config-change"
+    | "elicitation";
   content: string;
   timestamp: Date;
   toolName?: string;
@@ -162,6 +163,30 @@ export interface UserQuestionEvent {
   conversation_id?: string;
 }
 
+export interface ElicitationEvent {
+  message: string;
+  server_name?: string;
+  request_id?: string;
+  conversation_id?: string;
+}
+
+export interface ElicitationResultEvent {
+  action: string;
+  request_id?: string;
+  conversation_id?: string;
+}
+
+export interface StopFailureEvent {
+  stop_reason?: string;
+  error_type?: string;
+  conversation_id?: string;
+}
+
+export interface PostCompactEvent {
+  session_id?: string;
+  conversation_id?: string;
+}
+
 export type ConnectionStatus = "disconnected" | "connecting" | "connected" | "error";
 
 export interface Attachment {
diff --git a/src/routes/+page.svelte b/src/routes/+page.svelte
index 5aae88d..e77d9e8 100644
--- a/src/routes/+page.svelte
+++ b/src/routes/+page.svelte
@@ -36,6 +36,7 @@
   import type { CharacterState } from "$lib/types/states";
   import PermissionModal from "$lib/components/PermissionModal.svelte";
   import UserQuestionModal from "$lib/components/UserQuestionModal.svelte";
+  import ElicitationModal from "$lib/components/ElicitationModal.svelte";
   import ConfigSidebar from "$lib/components/ConfigSidebar.svelte";
   import AchievementsPanel from "$lib/components/AchievementsPanel.svelte";
   import ToastContainer from "$lib/components/ToastContainer.svelte";
@@ -593,6 +594,7 @@
 
     <PermissionModal />
     <UserQuestionModal />
+    <ElicitationModal />
     <ConfigSidebar />
     <AchievementsPanel
       bind:isOpen={achievementPanelOpen}