diff --git a/libs/clipboard/src/cliprdr.h b/libs/clipboard/src/cliprdr.h
index 9d56049ee..2edb473fd 100644
--- a/libs/clipboard/src/cliprdr.h
+++ b/libs/clipboard/src/cliprdr.h
@@ -150,6 +150,15 @@ extern "C"
 
     typedef struct _cliprdr_client_context CliprdrClientContext;
 
+    struct _NOTIFICATION_MESSAGE
+    {
+        // 0 - info, 1 - warning, 2 - error
+        UINT32 type;
+        char *msg;
+        char *details;
+    };
+    typedef struct _NOTIFICATION_MESSAGE NOTIFICATION_MESSAGE;
+
     typedef UINT (*pcCliprdrServerCapabilities)(CliprdrClientContext *context,
                                                 const CLIPRDR_CAPABILITIES *capabilities);
     typedef UINT (*pcCliprdrClientCapabilities)(CliprdrClientContext *context,
@@ -158,6 +167,9 @@ extern "C"
                                           const CLIPRDR_MONITOR_READY *monitorReady);
     typedef UINT (*pcCliprdrTempDirectory)(CliprdrClientContext *context,
                                            const CLIPRDR_TEMP_DIRECTORY *tempDirectory);
+
+    typedef UINT (*pcNotifyClipboardMsg)(const NOTIFICATION_MESSAGE *msg);
+
     typedef UINT (*pcCliprdrClientFormatList)(CliprdrClientContext *context,
                                               const CLIPRDR_FORMAT_LIST *formatList);
     typedef UINT (*pcCliprdrServerFormatList)(CliprdrClientContext *context,
@@ -204,6 +216,7 @@ extern "C"
         pcCliprdrClientCapabilities ClientCapabilities;
         pcCliprdrMonitorReady MonitorReady;
         pcCliprdrTempDirectory TempDirectory;
+        pcNotifyClipboardMsg NotifyClipboardMsg;
         pcCliprdrClientFormatList ClientFormatList;
         pcCliprdrServerFormatList ServerFormatList;
         pcCliprdrClientFormatListResponse ClientFormatListResponse;
@@ -229,4 +242,3 @@ extern "C"
 #endif
 
 #endif // WF_CLIPRDR_H__
-
diff --git a/libs/clipboard/src/cliprdr.rs b/libs/clipboard/src/cliprdr.rs
index 6bbb27ca0..60475f72b 100644
--- a/libs/clipboard/src/cliprdr.rs
+++ b/libs/clipboard/src/cliprdr.rs
@@ -324,6 +324,14 @@ pub struct _CLIPRDR_FILE_CONTENTS_RESPONSE {
 }
 pub type CLIPRDR_FILE_CONTENTS_RESPONSE = _CLIPRDR_FILE_CONTENTS_RESPONSE;
 pub type CliprdrClientContext = _cliprdr_client_context;
+#[repr(C)]
+#[derive(Debug, Copy, Clone)]
+pub struct _NOTIFICATION_MESSAGE {
+    pub r#type: UINT32, // 0 - info, 1 - warning, 2 - error
+    pub msg: *const BYTE,
+    pub details: *const BYTE,
+}
+pub type NOTIFICATION_MESSAGE = _NOTIFICATION_MESSAGE;
 pub type pcCliprdrServerCapabilities = ::std::option::Option<
     unsafe extern "C" fn(
         context: *mut CliprdrClientContext,
@@ -348,6 +356,8 @@ pub type pcCliprdrTempDirectory = ::std::option::Option<
         tempDirectory: *const CLIPRDR_TEMP_DIRECTORY,
     ) -> UINT,
 >;
+pub type pcNotifyClipboardMsg =
+    ::std::option::Option<unsafe extern "C" fn(msg: *const NOTIFICATION_MESSAGE) -> UINT>;
 pub type pcCliprdrClientFormatList = ::std::option::Option<
     unsafe extern "C" fn(
         context: *mut CliprdrClientContext,
@@ -458,6 +468,7 @@ pub struct _cliprdr_client_context {
     pub ClientCapabilities: pcCliprdrClientCapabilities,
     pub MonitorReady: pcCliprdrMonitorReady,
     pub TempDirectory: pcCliprdrTempDirectory,
+    pub NotifyClipboardMsg: pcNotifyClipboardMsg,
     pub ClientFormatList: pcCliprdrClientFormatList,
     pub ServerFormatList: pcCliprdrServerFormatList,
     pub ClientFormatListResponse: pcCliprdrClientFormatListResponse,
@@ -499,6 +510,8 @@ impl CliprdrClientContext {
     pub fn create(
         enable_files: bool,
         enable_others: bool,
+        response_wait_timeout_secs: u32,
+        notify_callback: pcNotifyClipboardMsg,
         client_format_list: pcCliprdrClientFormatList,
         client_format_list_response: pcCliprdrClientFormatListResponse,
         client_format_data_request: pcCliprdrClientFormatDataRequest,
@@ -511,11 +524,12 @@ impl CliprdrClientContext {
             EnableFiles: if enable_files { TRUE } else { FALSE },
             EnableOthers: if enable_others { TRUE } else { FALSE },
             IsStopped: FALSE,
-            ResponseWaitTimeoutSecs: 60,
+            ResponseWaitTimeoutSecs: response_wait_timeout_secs,
             ServerCapabilities: None,
             ClientCapabilities: None,
             MonitorReady: None,
             TempDirectory: None,
+            NotifyClipboardMsg: notify_callback,
             ClientFormatList: client_format_list,
             ServerFormatList: None,
             ClientFormatListResponse: client_format_list_response,
diff --git a/libs/clipboard/src/context_send.rs b/libs/clipboard/src/context_send.rs
index 16363250e..76f8e4d7a 100644
--- a/libs/clipboard/src/context_send.rs
+++ b/libs/clipboard/src/context_send.rs
@@ -2,6 +2,8 @@ use crate::cliprdr::*;
 use hbb_common::log;
 use std::sync::Mutex;
 
+const CLIPBOARD_RESPONSE_WAIT_TIMEOUT_SECS: u32 = 30;
+
 lazy_static::lazy_static! {
     static ref CONTEXT_SEND: ContextSend = ContextSend{addr: Mutex::new(0)};
 }
@@ -27,7 +29,11 @@ impl ContextSend {
         let mut lock = CONTEXT_SEND.addr.lock().unwrap();
         if enabled {
             if *lock == 0 {
-                match crate::create_cliprdr_context(true, false) {
+                match crate::create_cliprdr_context(
+                    true,
+                    false,
+                    CLIPBOARD_RESPONSE_WAIT_TIMEOUT_SECS,
+                ) {
                     Ok(context) => {
                         log::info!("clipboard context for file transfer created.");
                         *lock = Box::into_raw(context) as _;
diff --git a/libs/clipboard/src/lib.rs b/libs/clipboard/src/lib.rs
index c63817415..152dc0bcc 100644
--- a/libs/clipboard/src/lib.rs
+++ b/libs/clipboard/src/lib.rs
@@ -446,10 +446,13 @@ pub fn server_file_contents_response(
 pub fn create_cliprdr_context(
     enable_files: bool,
     enable_others: bool,
+    response_wait_timeout_secs: u32,
 ) -> ResultType<Box<CliprdrClientContext>> {
     Ok(CliprdrClientContext::create(
         enable_files,
         enable_others,
+        response_wait_timeout_secs,
+        Some(notify_callback),
         Some(client_format_list),
         Some(client_format_list_response),
         Some(client_format_data_request),
@@ -459,6 +462,13 @@ pub fn create_cliprdr_context(
     )?)
 }
 
+extern "C" fn notify_callback(
+    msg: *const NOTIFICATION_MESSAGE,
+) -> UINT {
+    log::debug!("notify_callback called");
+    0
+}
+
 extern "C" fn client_format_list(
     _context: *mut CliprdrClientContext,
     clip_format_list: *const CLIPRDR_FORMAT_LIST,
diff --git a/libs/clipboard/src/windows/wf_cliprdr.c b/libs/clipboard/src/windows/wf_cliprdr.c
index ea582d5b1..b9939121d 100644
--- a/libs/clipboard/src/windows/wf_cliprdr.c
+++ b/libs/clipboard/src/windows/wf_cliprdr.c
@@ -1455,7 +1455,8 @@ UINT wait_response_event(wfClipboard *clipboard, HANDLE event, void **data)
 	clipboard->context->IsStopped = FALSE;
 	DWORD waitOnceTimeoutMillis = 50;
 	int waitCount = 1000 * clipboard->context->ResponseWaitTimeoutSecs / waitOnceTimeoutMillis;
-	for (int i = 0; i < waitCount * 3; i++)
+	int i = 0;
+	for (; i < waitCount; i++)
 	{
 		DWORD waitRes = WaitForSingleObject(event, waitOnceTimeoutMillis);
 		if (waitRes == WAIT_TIMEOUT && clipboard->context->IsStopped == FALSE)
@@ -1488,6 +1489,16 @@ UINT wait_response_event(wfClipboard *clipboard, HANDLE event, void **data)
 		return rc;
 	}
 
+	if (i == waitCount)
+	{
+		NOTIFICATION_MESSAGE msg;
+		msg.type = 2;
+		msg.msg = "timeout waiting for response";
+		msg.details = NULL;
+		clipboard->context->NotifyClipboardMsg(&msg);
+		rc = ERROR_INTERNAL_ERROR;
+	}
+
 	if ((*data) != NULL)
 	{
 		if (!ResetEvent(event))