diff --git a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/webview/BrowserConnector.kt b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/webview/BrowserConnector.kt
index ebe5858d97e..87f977adfa1 100644
--- a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/webview/BrowserConnector.kt
+++ b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/webview/BrowserConnector.kt
@@ -22,6 +22,7 @@ import kotlinx.coroutines.launch
 import org.cef.browser.CefBrowser
 import org.eclipse.lsp4j.Position
 import org.eclipse.lsp4j.Range
+import software.aws.toolkits.core.utils.error
 import software.aws.toolkits.core.utils.getLogger
 import software.aws.toolkits.core.utils.warn
 import software.aws.toolkits.jetbrains.services.amazonq.apps.AppConnection
@@ -31,7 +32,6 @@ import software.aws.toolkits.jetbrains.services.amazonq.lsp.AmazonQLspService
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.encryption.JwtEncryptionManager
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.flareChat.AwsServerCapabilitiesProvider
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.flareChat.ChatCommunicationManager
-import software.aws.toolkits.jetbrains.services.amazonq.lsp.flareChat.ChatCommunicationManager.Companion.convertToJsonToSendToChat
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.flareChat.getTextDocumentIdentifier
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.ButtonClickNotification
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.ButtonClickParams
@@ -416,8 +416,18 @@ class BrowserConnector(
                         server, params ->
                     val result = server.tabBarActions(params)
                     result.whenComplete { params1, error ->
-                        val res = ChatCommunicationManager.convertNotificationToJsonForChat(CHAT_TAB_BAR_ACTIONS, params1)
-                        browser.postChat(res)
+                        try {
+                            if (error != null) {
+                                throw error
+                            }
+                            val res = ChatCommunicationManager.convertNotificationToJsonForChat(CHAT_TAB_BAR_ACTIONS, params1)
+                            browser.postChat(res)
+                        } catch (e: Exception) {
+                            LOG.error { "Failed to perform chat tab bar action $e" }
+                            params.tabId?.let {
+                                browser.postChat(chatCommunicationManager.getErrorUiMessage(it, e, null))
+                            }
+                        }
                     }
                 }
             }
@@ -443,7 +453,7 @@ class BrowserConnector(
                     )
                 )
 
-                val uiMessage = convertToJsonToSendToChat(
+                val uiMessage = ChatCommunicationManager.convertToJsonToSendToChat(
                     command = SEND_CHAT_COMMAND_PROMPT,
                     tabId = stopResponseRequest.params.tabId,
                     params = paramsJson.toString(),
@@ -462,15 +472,23 @@ class BrowserConnector(
         browser: Browser,
     ) {
         result.whenComplete { value, error ->
-            chatCommunicationManager.removePartialChatMessage(partialResultToken)
-            val messageToChat = ChatCommunicationManager.convertToJsonToSendToChat(
-                SEND_CHAT_COMMAND_PROMPT,
-                tabId,
-                encryptionManager?.decrypt(value).orEmpty(),
-                isPartialResult = false
-            )
-            browser.postChat(messageToChat)
-            chatCommunicationManager.removeInflightRequestForTab(tabId)
+            try {
+                if (error != null) {
+                    throw error
+                }
+                chatCommunicationManager.removePartialChatMessage(partialResultToken)
+                val messageToChat = ChatCommunicationManager.convertToJsonToSendToChat(
+                    SEND_CHAT_COMMAND_PROMPT,
+                    tabId,
+                    encryptionManager?.decrypt(value).orEmpty(),
+                    isPartialResult = false
+                )
+                browser.postChat(messageToChat)
+                chatCommunicationManager.removeInflightRequestForTab(tabId)
+            } catch (e: Exception) {
+                LOG.error { "Failed to send chat message $e" }
+                browser.postChat(chatCommunicationManager.getErrorUiMessage(tabId, e, partialResultToken))
+            }
         }
     }
 
diff --git a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/flareChat/ChatCommunicationManager.kt b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/flareChat/ChatCommunicationManager.kt
index 90a321b24c5..67116573e1f 100644
--- a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/flareChat/ChatCommunicationManager.kt
+++ b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/flareChat/ChatCommunicationManager.kt
@@ -10,6 +10,8 @@ import com.intellij.openapi.project.Project
 import org.eclipse.lsp4j.ProgressParams
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.AmazonQLspService
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.flareChat.ProgressNotificationUtils.getObject
+import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.CHAT_ERROR_PARAMS
+import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.ErrorParams
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.GetSerializedChatResult
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.OpenTabResult
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.SEND_CHAT_COMMAND_PROMPT
@@ -70,6 +72,25 @@ class ChatCommunicationManager {
         }
     }
 
+    fun getErrorUiMessage(tabId: String, exception: Exception, token: String?): String {
+        token?.let {
+            removePartialChatMessage(it)
+        }
+        val errorTitle = "An error occurred while processing your request."
+        val errorMessage = "Details: ${exception.message}"
+        val errorParams = Gson().toJson(ErrorParams(tabId, null, errorMessage, errorTitle)).toString()
+        val isPartialResult = false
+        val uiMessage = """
+                {
+                "command":"$CHAT_ERROR_PARAMS",
+                "tabId": "$tabId",
+                "params": $errorParams,
+                "isPartialResult": $isPartialResult
+                }
+        """.trimIndent()
+        return uiMessage
+    }
+
     companion object {
         fun getInstance(project: Project) = project.service<ChatCommunicationManager>()
 
diff --git a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/model/aws/chat/ErrorParams.kt b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/model/aws/chat/ErrorParams.kt
new file mode 100644
index 00000000000..225fa3a20c1
--- /dev/null
+++ b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/model/aws/chat/ErrorParams.kt
@@ -0,0 +1,11 @@
+// Copyright 2025 Amazon.com, Inc. or its affiliates. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+package software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat
+
+data class ErrorParams(
+    val tabId: String,
+    val triggerType: String?,
+    val message: String,
+    val title: String,
+)
diff --git a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/model/aws/chat/FlareChatCommands.kt b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/model/aws/chat/FlareChatCommands.kt
index 8c8b830a07e..6b7d5a1f3e5 100644
--- a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/model/aws/chat/FlareChatCommands.kt
+++ b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/model/aws/chat/FlareChatCommands.kt
@@ -32,4 +32,5 @@ const val CHAT_CREATE_PROMPT = "aws/chat/createPrompt"
 const val SHOW_SAVE_FILE_DIALOG_REQUEST_METHOD = "aws/showSaveFileDialog"
 const val GET_SERIALIZED_CHAT_REQUEST_METHOD = "aws/chat/getSerializedChat"
 const val OPEN_FILE_DIFF = "aws/openFileDiff"
+const val CHAT_ERROR_PARAMS = "errorMessage"
 const val STOP_CHAT_RESPONSE = "stopChatResponse"