diff --git a/crates/tui/src/core/engine.rs b/crates/tui/src/core/engine.rs
index 54ba0c243..54af77db4 100644
--- a/crates/tui/src/core/engine.rs
+++ b/crates/tui/src/core/engine.rs
@@ -375,6 +375,8 @@ pub struct Engine {
     /// This keeps prompt refreshes cheap while still noticing append/update
     /// writes from slop ledger tools during the same session.
     slop_ledger_gate_cache: Option<(Option<SystemTime>, Option<String>)>,
+    /// Current operating mode. Updated on `ChangeMode` and `SendMessage`.
+    current_mode: AppMode,
 }
 
 // === Internal tool helpers ===
@@ -621,6 +623,7 @@ impl Engine {
             slop_ledger_gate_cache: None,
             workshop_vars,
             sandbox_backend,
+            current_mode: AppMode::Agent,
         };
         engine.rehydrate_latest_canonical_state();
 
@@ -1046,11 +1049,23 @@ impl Engine {
                     let _ = self.tx_event.send(Event::AgentList { agents }).await;
                 }
                 Op::ChangeMode { mode } => {
+                    let previous_mode = self.current_mode;
+                    self.current_mode = mode;
                     self.refresh_system_prompt(mode);
                     self.emit_session_updated().await;
+                    // Notify the agent that the mode has changed so it can re-evaluate
+                    // any operations that were blocked by the previous mode's policy.
+                    if previous_mode != mode {
+                        let msg = Self::mode_change_runtime_message(previous_mode, mode);
+                        self.session.add_message(msg);
+                        self.emit_session_updated().await;
+                    }
                     let _ = self
                         .tx_event
-                        .send(Event::status(format!("Mode changed to: {mode:?}")))
+                        .send(Event::status(format!(
+                            "Mode changed to: {}",
+                            mode.description()
+                        )))
                         .await;
                 }
                 Op::SetModel { model, mode } => {
@@ -1190,6 +1205,47 @@ impl Engine {
             .await;
     }
 
+    /// Build a runtime event message notifying the agent that the operating mode has changed.
+    /// This lets the agent re-evaluate any operations that were blocked by the previous mode.
+    fn mode_change_runtime_message(previous_mode: AppMode, new_mode: AppMode) -> Message {
+        let (policy_note, re_eval_hint) = match new_mode {
+            AppMode::Yolo => (
+                "all operations run automatically without requiring user approval",
+                "Re-evaluate any previously blocked write, patch, or shell operations \
+                 — they are now auto-approved.",
+            ),
+            AppMode::Agent => (
+                "read-only operations run silently; writes, patches, and shell \
+                 commands require user approval",
+                "Any operations you ran automatically under YOLO mode now require \
+                 explicit user approval before executing.",
+            ),
+            AppMode::Plan => (
+                "all writes and patches are blocked; shell and code execution are unavailable",
+                "Any previously planned operations that require writes or shell access \
+                 must wait until the mode changes back to Agent or YOLO.",
+            ),
+        };
+        Message {
+            role: "user".to_string(),
+            content: vec![ContentBlock::Text {
+                text: format!(
+                    "<codewhale:runtime_event kind=\"mode_change\" visibility=\"internal\">\n\
+This is an internal runtime event, not user input. The operating mode has changed \
+from {previous} mode to {new} mode.\n\n\
+In {new} mode: {policy}\n\n\
+{re_eval}\n\
+</codewhale:runtime_event>",
+                    previous = previous_mode.description(),
+                    new = new_mode.description(),
+                    policy = policy_note,
+                    re_eval = re_eval_hint,
+                ),
+                cache_control: None,
+            }],
+        }
+    }
+
     async fn add_session_message(&mut self, message: Message) {
         self.session.add_message(message);
         self.emit_session_updated().await;
@@ -1198,11 +1254,13 @@ impl Engine {
     fn turn_metadata_block(
         &self,
         routed_model: &str,
+        mode: AppMode,
         auto_model: bool,
         reasoning_effort: Option<&str>,
         reasoning_effort_auto: bool,
     ) -> ContentBlock {
         let today = chrono::Local::now().format("%Y-%m-%d").to_string();
+        let mode_label = mode.description();
         let working_set_summary = self
             .session
             .working_set
@@ -1212,6 +1270,7 @@ impl Engine {
 
         let mut lines = vec![
             format!("Current local date: {today}"),
+            format!("Current mode: {mode_label}"),
             format!("Current model: {routed_model}"),
         ];
         if auto_model {
@@ -1234,6 +1293,7 @@ impl Engine {
     fn user_text_message_with_turn_metadata(&self, text: String) -> Message {
         self.user_text_message_with_turn_metadata_for_route(
             text,
+            self.current_mode,
             &self.session.model,
             self.session.auto_model,
             self.session.reasoning_effort.as_deref(),
@@ -1244,6 +1304,7 @@ impl Engine {
     fn user_text_message_with_turn_metadata_for_route(
         &self,
         text: String,
+        mode: AppMode,
         routed_model: &str,
         auto_model: bool,
         reasoning_effort: Option<&str>,
@@ -1254,6 +1315,7 @@ impl Engine {
             content: vec![
                 self.turn_metadata_block(
                     routed_model,
+                    mode,
                     auto_model,
                     reasoning_effort,
                     reasoning_effort_auto,
@@ -1289,6 +1351,9 @@ impl Engine {
         // Reset cancel token for fresh turn (in case previous was cancelled)
         self.reset_cancel_token();
 
+        // Track current mode so mid-turn messages include the right mode in turn metadata.
+        self.current_mode = mode;
+
         // Drain stale steer messages from previous turns.
         while self.rx_steer.try_recv().is_ok() {}
 
@@ -1368,6 +1433,7 @@ impl Engine {
         // Add user message to session
         let user_msg = self.user_text_message_with_turn_metadata_for_route(
             content,
+            mode,
             &model,
             auto_model,
             reasoning_effort.as_deref(),
diff --git a/crates/tui/src/core/engine/tests.rs b/crates/tui/src/core/engine/tests.rs
index 48491277e..d058a00e0 100644
--- a/crates/tui/src/core/engine/tests.rs
+++ b/crates/tui/src/core/engine/tests.rs
@@ -1617,6 +1617,61 @@ async fn change_mode_refreshes_session_prompt_and_updates_session() {
     assert!(prompt.contains("Approval Policy: Auto"));
 }
 
+#[tokio::test]
+async fn change_mode_op_injects_runtime_event_into_session_messages() {
+    let tmp = tempdir().expect("tempdir");
+    let config = EngineConfig {
+        workspace: tmp.path().to_path_buf(),
+        model: "deepseek-v4-pro".to_string(),
+        ..Default::default()
+    };
+    let (engine, handle) = Engine::new(config, &Config::default());
+
+    let run = tokio::spawn(engine.run());
+    // Switch from default Agent → YOLO
+    handle
+        .send(Op::ChangeMode {
+            mode: AppMode::Yolo,
+        })
+        .await
+        .expect("send change mode");
+
+    // Collect session-updated events until we see the injected message
+    let messages = {
+        let mut rx = handle.rx_event.write().await;
+        loop {
+            let event = tokio::time::timeout(std::time::Duration::from_secs(2), rx.recv())
+                .await
+                .expect("session update after mode switch")
+                .expect("event");
+            if let Event::SessionUpdated { messages, .. } = event {
+                // The last message should be our runtime event
+                if let Some(last) = messages.last()
+                    && let ContentBlock::Text { text, .. } =
+                        last.content.first().expect("text block")
+                    && text.contains("kind=\"mode_change\"")
+                {
+                    break messages;
+                }
+            }
+        }
+    };
+    run.abort();
+
+    let last = messages.last().expect("at least one message");
+    let ContentBlock::Text { text, .. } = last.content.first().expect("text block") else {
+        panic!("expected text block");
+    };
+    assert!(
+        text.contains("Agent mode") && text.contains("YOLO mode"),
+        "should contain both previous and new mode: {text}"
+    );
+    assert!(
+        text.contains("Re-evaluate"),
+        "should tell agent to re-evaluate: {text}"
+    );
+}
+
 #[test]
 fn detects_context_length_errors_from_provider_payloads() {
     let msg = r#"SSE stream request failed: HTTP 400 Bad Request: {"error":{"message":"This model's maximum context length is 131072 tokens. However, you requested 153056 tokens (148960 in the messages, 4096 in the completion).","type":"invalid_request_error"}}"#;
@@ -2042,6 +2097,7 @@ fn turn_metadata_includes_auto_model_route() {
 
     let user_msg = engine.user_text_message_with_turn_metadata_for_route(
         "debug this regression".to_string(),
+        AppMode::Agent,
         "deepseek-v4-pro",
         true,
         Some("max"),
@@ -2058,6 +2114,94 @@ fn turn_metadata_includes_auto_model_route() {
     assert!(!text.contains("debug this regression"));
 }
 
+#[test]
+fn turn_metadata_includes_current_mode() {
+    let tmp = tempdir().expect("tempdir");
+    let config = EngineConfig {
+        workspace: tmp.path().to_path_buf(),
+        ..Default::default()
+    };
+    let (engine, _handle) = Engine::new(config, &Config::default());
+
+    let user_msg = engine.user_text_message_with_turn_metadata_for_route(
+        "test mode metadata".to_string(),
+        AppMode::Yolo,
+        "deepseek-v4-flash",
+        false,
+        None,
+        false,
+    );
+    let first_block = user_msg.content.first().expect("turn metadata block");
+    let ContentBlock::Text { text, .. } = first_block else {
+        panic!("expected text metadata block");
+    };
+
+    assert!(
+        text.contains("Current mode: YOLO mode - full tool access without approvals"),
+        "turn metadata should include the current mode label, got: {text}"
+    );
+}
+
+#[test]
+fn turn_metadata_mode_updates_with_change_mode_op() {
+    let tmp = tempdir().expect("tempdir");
+    let config = EngineConfig {
+        workspace: tmp.path().to_path_buf(),
+        ..Default::default()
+    };
+    let (mut engine, _handle) = Engine::new(config, &Config::default());
+
+    // In agent mode by default
+    let msg = engine.user_text_message_with_turn_metadata("hello".to_string());
+    let first_block = msg.content.first().expect("turn metadata block");
+    let ContentBlock::Text { text, .. } = first_block else {
+        panic!("expected text metadata block");
+    };
+    assert!(
+        text.contains("Agent mode"),
+        "initial mode should be Agent, got: {text}"
+    );
+
+    // Switch to YOLO — user_text_message_with_turn_metadata should reflect the new mode
+    engine.current_mode = AppMode::Yolo;
+    let msg = engine.user_text_message_with_turn_metadata("hello again".to_string());
+    let first_block = msg.content.first().expect("turn metadata block");
+    let ContentBlock::Text { text, .. } = first_block else {
+        panic!("expected text metadata block");
+    };
+    assert!(
+        text.contains("YOLO mode"),
+        "mode after change should be YOLO, got: {text}"
+    );
+}
+
+#[test]
+fn mode_change_runtime_message_format() {
+    let msg = Engine::mode_change_runtime_message(AppMode::Agent, AppMode::Yolo);
+
+    assert_eq!(msg.role, "user");
+    let ContentBlock::Text { text, .. } = msg.content.first().expect("text block") else {
+        panic!("expected text block");
+    };
+
+    assert!(
+        text.contains("codewhale:runtime_event"),
+        "should be a runtime event message"
+    );
+    assert!(
+        text.contains("kind=\"mode_change\""),
+        "should have mode_change kind"
+    );
+    assert!(
+        text.contains("Agent mode") && text.contains("YOLO mode"),
+        "should mention both previous and new mode: {text}"
+    );
+    assert!(
+        text.contains("Re-evaluate"),
+        "should tell agent to re-evaluate blocked operations: {text}"
+    );
+}
+
 #[test]
 fn user_text_message_keeps_current_turn_input_after_turn_metadata() {
     let tmp = tempdir().expect("tempdir");
diff --git a/crates/tui/src/core/engine/turn_loop.rs b/crates/tui/src/core/engine/turn_loop.rs
index 6b7ffd1ff..472bc9bc7 100644
--- a/crates/tui/src/core/engine/turn_loop.rs
+++ b/crates/tui/src/core/engine/turn_loop.rs
@@ -314,7 +314,9 @@ impl Engine {
             // Three-zone prefix contract (#2264): freeze baseline on first
             // turn, verify against it on subsequent turns. Operates alongside
             // PrefixStabilityManager as an independent diagnostic layer.
-            // Phase 2: warn-only, auto-re-freeze on drift.
+            // Phase 3: emit a one-shot 'frozen' event on first turn.
+            // Drift is logged (tracing::debug!) but not re-emitted —
+            // PrefixStabilityManager already reports the change above.
             let system_text =
                 crate::prefix_cache::system_prompt_text(self.session.system_prompt.as_ref());
             let current_tools: &[crate::models::Tool] = active_tools.as_deref().unwrap_or_default();
@@ -338,7 +340,19 @@ impl Engine {
                         self.session.system_prompt.as_ref(),
                         current_tools.to_vec(),
                     );
-                    self.session.frozen_prefix = Some(pinned.freeze());
+                    let frozen = pinned.freeze();
+                    let _ = self
+                        .tx_event
+                        .send(Event::PrefixCacheChange {
+                            description: format!("frozen: {}", frozen.short_id()),
+                            system_prompt_changed: false,
+                            tools_changed: false,
+                            stability_pct: 100,
+                            changed: false,
+                            pinned_combined_hash: frozen.hash().to_string(),
+                        })
+                        .await;
+                    self.session.frozen_prefix = Some(frozen);
                 }
             }