diff --git a/packages/amazonq/.changes/next-release/Bug Fix-704d175a-a99f-4ce7-bf08-b94d6f7218c0.json b/packages/amazonq/.changes/next-release/Bug Fix-704d175a-a99f-4ce7-bf08-b94d6f7218c0.json
new file mode 100644
index 00000000000..01d6ec7c8b0
--- /dev/null
+++ b/packages/amazonq/.changes/next-release/Bug Fix-704d175a-a99f-4ce7-bf08-b94d6f7218c0.json	
@@ -0,0 +1,4 @@
+{
+	"type": "Bug Fix",
+	"description": "`Send to prompt` and other context menu options not sent if chat was closed"
+}
diff --git a/packages/core/src/amazonq/apps/initContext.ts b/packages/core/src/amazonq/apps/initContext.ts
index e33fafca7c3..f8b06e4b46a 100644
--- a/packages/core/src/amazonq/apps/initContext.ts
+++ b/packages/core/src/amazonq/apps/initContext.ts
@@ -4,20 +4,20 @@
  */
 
 import { EventEmitter } from 'vscode'
-import { MessagePublisher } from '../messages/messagePublisher'
+import { MessagePublisher, UiMessagePublisher } from '../messages/messagePublisher'
 import { MessageListener } from '../messages/messageListener'
 import { TabType } from '../webview/ui/storages/tabsStorage'
 
 export interface AmazonQAppInitContext {
     registerWebViewToAppMessagePublisher(eventEmitter: MessagePublisher<any>, tabType: TabType): void
-    getAppsToWebViewMessagePublisher(): MessagePublisher<any>
+    getAppsToWebViewMessagePublisher(): UiMessagePublisher<any>
     onDidChangeAmazonQVisibility: EventEmitter<boolean>
 }
 
 export class DefaultAmazonQAppInitContext implements AmazonQAppInitContext {
     private readonly appsToWebViewEventEmitter = new EventEmitter<any>()
     private readonly appsToWebViewMessageListener = new MessageListener<any>(this.appsToWebViewEventEmitter)
-    private readonly appsToWebViewMessagePublisher = new MessagePublisher<any>(this.appsToWebViewEventEmitter)
+    private readonly appsToWebViewMessagePublisher = new UiMessagePublisher<any>(this.appsToWebViewEventEmitter)
     private readonly webViewToAppsMessagePublishers: Map<TabType, MessagePublisher<any>> = new Map()
     public readonly onDidChangeAmazonQVisibility = new EventEmitter<boolean>()
 
@@ -41,7 +41,7 @@ export class DefaultAmazonQAppInitContext implements AmazonQAppInitContext {
         return this.appsToWebViewMessageListener
     }
 
-    getAppsToWebViewMessagePublisher(): MessagePublisher<any> {
+    getAppsToWebViewMessagePublisher(): UiMessagePublisher<any> {
         return this.appsToWebViewMessagePublisher
     }
 }
diff --git a/packages/core/src/amazonq/messages/messagePublisher.ts b/packages/core/src/amazonq/messages/messagePublisher.ts
index d2987a99536..7fa6976b9a9 100644
--- a/packages/core/src/amazonq/messages/messagePublisher.ts
+++ b/packages/core/src/amazonq/messages/messagePublisher.ts
@@ -12,3 +12,48 @@ export class MessagePublisher<T> {
         this.eventEmitter.fire(event)
     }
 }
+
+/**
+ * Same as {@link MessagePublisher}, but will wait until the UI indicates it
+ * is ready to recieve messages, before the message is published.
+ *
+ * This solves a problem when running a right click menu option like
+ * "Send To Prompt" BUT chat is not opened yet, it would result in the prompt failing to
+ * be recieved by chat.
+ */
+export class UiMessagePublisher<T> extends MessagePublisher<T> {
+    private isUiReady: boolean = false
+    private buffer: T[] = []
+
+    constructor(eventEmitter: EventEmitter<T>) {
+        super(eventEmitter)
+    }
+
+    public override publish(event: T): void {
+        // immediately send if Chat UI is ready
+        if (this.isUiReady) {
+            super.publish(event)
+            return
+        }
+
+        this.buffer.push(event)
+    }
+
+    /**
+     * Indicate the Q Chat UI is ready to recieve messages.
+     */
+    public setUiReady() {
+        this.isUiReady = true
+        this.flush()
+    }
+
+    /**
+     * Publishes all blocked messages
+     */
+    private flush() {
+        for (const msg of this.buffer) {
+            super.publish(msg)
+        }
+        this.buffer = []
+    }
+}
diff --git a/packages/core/src/amazonq/webview/messages/messageDispatcher.ts b/packages/core/src/amazonq/webview/messages/messageDispatcher.ts
index 8acd04e8953..fdd1584b767 100644
--- a/packages/core/src/amazonq/webview/messages/messageDispatcher.ts
+++ b/packages/core/src/amazonq/webview/messages/messageDispatcher.ts
@@ -13,6 +13,7 @@ import { telemetry } from '../../../shared/telemetry'
 import { AmazonQChatMessageDuration } from '../../messages/chatMessageDuration'
 import { globals, openUrl } from '../../../shared'
 import { isClickTelemetry, isOpenAgentTelemetry } from '../ui/telemetry/actions'
+import { DefaultAmazonQAppInitContext } from '../../apps/initContext'
 
 export function dispatchWebViewMessagesToApps(
     webview: Webview,
@@ -21,12 +22,12 @@ export function dispatchWebViewMessagesToApps(
     webview.onDidReceiveMessage((msg) => {
         switch (msg.command) {
             case 'ui-is-ready': {
+                DefaultAmazonQAppInitContext.instance.getAppsToWebViewMessagePublisher().setUiReady()
                 /**
                  * ui-is-ready isn't associated to any tab so just record the telemetry event and continue.
                  * This would be equivalent of the duration between "user clicked open q" and "ui has become available"
                  * NOTE: Amazon Q UI is only loaded ONCE. The state is saved between each hide/show of the webview.
                  */
-
                 telemetry.webview_load.emit({
                     webviewName: 'amazonq',
                     duration: performance.measure(amazonqMark.uiReady, amazonqMark.open).duration,
diff --git a/packages/core/src/shared/logger/logger.ts b/packages/core/src/shared/logger/logger.ts
index d5bf5f13380..19be5ac2887 100644
--- a/packages/core/src/shared/logger/logger.ts
+++ b/packages/core/src/shared/logger/logger.ts
@@ -5,7 +5,7 @@
 
 import * as vscode from 'vscode'
 
-export type LogTopic = 'crashMonitoring' | 'dev/beta' | 'notifications' | 'test' | 'childProcess' | 'unknown'
+export type LogTopic = 'crashMonitoring' | 'dev/beta' | 'notifications' | 'test' | 'childProcess' | 'unknown' | 'chat'
 
 class ErrorLog {
     constructor(