diff --git a/packages/coding-agent/src/core/agent-session.ts b/packages/coding-agent/src/core/agent-session.ts
index 4a845f0d..c2e55f55 100644
--- a/packages/coding-agent/src/core/agent-session.ts
+++ b/packages/coding-agent/src/core/agent-session.ts
@@ -107,6 +107,7 @@ export class AgentSession {
 
 	// Bash execution state
 	private _bashAbortController: AbortController | null = null;
+	private _pendingBashMessages: BashExecutionMessage[] = [];
 
 	constructor(config: AgentSessionConfig) {
 		this.agent = config.agent;
@@ -120,6 +121,34 @@ export class AgentSession {
 	// Event Subscription
 	// =========================================================================
 
+	/** Internal handler for agent events - shared by subscribe and reconnect */
+	private _handleAgentEvent = async (event: AgentEvent): Promise<void> => {
+		// Notify all listeners
+		for (const l of this._eventListeners) {
+			l(event);
+		}
+
+		// Handle session persistence
+		if (event.type === "message_end") {
+			this.sessionManager.saveMessage(event.message);
+
+			// Initialize session after first user+assistant exchange
+			if (this.sessionManager.shouldInitializeSession(this.agent.state.messages)) {
+				this.sessionManager.startSession(this.agent.state);
+			}
+
+			// Check auto-compaction after assistant messages
+			if (event.message.role === "assistant") {
+				await this.checkAutoCompaction();
+			}
+		}
+
+		// Flush pending bash messages after agent turn completes
+		if (event.type === "agent_end") {
+			this._flushPendingBashMessages();
+		}
+	};
+
 	/**
 	 * Subscribe to agent events.
 	 * Session persistence is handled internally (saves messages on message_end).
@@ -130,27 +159,7 @@ export class AgentSession {
 
 		// Set up agent subscription if not already done
 		if (!this._unsubscribeAgent) {
-			this._unsubscribeAgent = this.agent.subscribe(async (event) => {
-				// Notify all listeners
-				for (const l of this._eventListeners) {
-					l(event);
-				}
-
-				// Handle session persistence
-				if (event.type === "message_end") {
-					this.sessionManager.saveMessage(event.message);
-
-					// Initialize session after first user+assistant exchange
-					if (this.sessionManager.shouldInitializeSession(this.agent.state.messages)) {
-						this.sessionManager.startSession(this.agent.state);
-					}
-
-					// Check auto-compaction after assistant messages
-					if (event.message.role === "assistant") {
-						await this.checkAutoCompaction();
-					}
-				}
-			});
+			this._unsubscribeAgent = this.agent.subscribe(this._handleAgentEvent);
 		}
 
 		// Return unsubscribe function for this specific listener
@@ -180,25 +189,7 @@ export class AgentSession {
 	 */
 	private _reconnectToAgent(): void {
 		if (this._unsubscribeAgent) return; // Already connected
-
-		this._unsubscribeAgent = this.agent.subscribe(async (event) => {
-			for (const l of this._eventListeners) {
-				l(event);
-			}
-
-			if (event.type === "message_end") {
-				this.sessionManager.saveMessage(event.message);
-
-				if (this.sessionManager.shouldInitializeSession(this.agent.state.messages)) {
-					this.sessionManager.startSession(this.agent.state);
-				}
-
-				// Check auto-compaction after assistant messages
-				if (event.message.role === "assistant") {
-					await this.checkAutoCompaction();
-				}
-			}
-		});
+		this._unsubscribeAgent = this.agent.subscribe(this._handleAgentEvent);
 	}
 
 	/**
@@ -673,15 +664,21 @@ export class AgentSession {
 				timestamp: Date.now(),
 			};
 
-			// Add to agent state
-			this.agent.appendMessage(bashMessage);
+			// If agent is streaming, defer adding to avoid breaking tool_use/tool_result ordering
+			if (this.isStreaming) {
+				// Queue for later - will be flushed on agent_end
+				this._pendingBashMessages.push(bashMessage);
+			} else {
+				// Add to agent state immediately
+				this.agent.appendMessage(bashMessage);
 
-			// Save to session
-			this.sessionManager.saveMessage(bashMessage);
+				// Save to session
+				this.sessionManager.saveMessage(bashMessage);
 
-			// Initialize session if needed
-			if (this.sessionManager.shouldInitializeSession(this.agent.state.messages)) {
-				this.sessionManager.startSession(this.agent.state);
+				// Initialize session if needed
+				if (this.sessionManager.shouldInitializeSession(this.agent.state.messages)) {
+					this.sessionManager.startSession(this.agent.state);
+				}
 			}
 
 			return result;
@@ -702,6 +699,29 @@ export class AgentSession {
 		return this._bashAbortController !== null;
 	}
 
+	/**
+	 * Flush pending bash messages to agent state and session.
+	 * Called after agent turn completes to maintain proper message ordering.
+	 */
+	private _flushPendingBashMessages(): void {
+		if (this._pendingBashMessages.length === 0) return;
+
+		for (const bashMessage of this._pendingBashMessages) {
+			// Add to agent state
+			this.agent.appendMessage(bashMessage);
+
+			// Save to session
+			this.sessionManager.saveMessage(bashMessage);
+		}
+
+		// Initialize session if needed
+		if (this.sessionManager.shouldInitializeSession(this.agent.state.messages)) {
+			this.sessionManager.startSession(this.agent.state);
+		}
+
+		this._pendingBashMessages = [];
+	}
+
 	// =========================================================================
 	// Session Management
 	// =========================================================================