diff --git a/Ink Canvas/MainWindow.xaml.cs b/Ink Canvas/MainWindow.xaml.cs
index 79c2e7da..f5626d32 100644
--- a/Ink Canvas/MainWindow.xaml.cs	
+++ b/Ink Canvas/MainWindow.xaml.cs	
@@ -834,6 +834,10 @@ namespace Ink_Canvas
 
             if (AvailableLatestVersion != null)
             {
+                // 检测到新版本，停止重试定时器
+                timerCheckAutoUpdateRetry.Stop();
+                updateCheckRetryCount = 0;
+                
                 // 检测到新版本
                 LogHelper.WriteLogToFile($"AutoUpdate | New version available: {AvailableLatestVersion}");
 
@@ -999,6 +1003,16 @@ namespace Ink_Canvas
             }
             else
             {
+                // 检查更新失败，启动重试定时器
+                LogHelper.WriteLogToFile("AutoUpdate | Update check failed, starting retry timer");
+                
+                // 重置重试计数
+                updateCheckRetryCount = 0;
+                
+                // 启动重试定时器，10分钟后重新检查
+                timerCheckAutoUpdateRetry.Start();
+                
+                // 清理更新文件夹
                 AutoUpdateHelper.DeleteUpdatesFolder();
             }
         }
diff --git a/Ink Canvas/MainWindow_cs/MW_Settings.cs b/Ink Canvas/MainWindow_cs/MW_Settings.cs
index 5c06d12f..3e8dc065 100644
--- a/Ink Canvas/MainWindow_cs/MW_Settings.cs	
+++ b/Ink Canvas/MainWindow_cs/MW_Settings.cs	
@@ -3126,6 +3126,7 @@ namespace Ink_Canvas
                 if (Settings.Startup.IsAutoUpdate)
                 {
                     LogHelper.WriteLogToFile($"AutoUpdate | Channel changed to {newChannel}, performing immediate update check");
+                    ResetUpdateCheckRetry();
 
                     // 执行完整的更新检查
                     await Task.Run(async () =>
diff --git a/Ink Canvas/MainWindow_cs/MW_Timer.cs b/Ink Canvas/MainWindow_cs/MW_Timer.cs
index c8d97dd9..8b83a223 100644
--- a/Ink Canvas/MainWindow_cs/MW_Timer.cs	
+++ b/Ink Canvas/MainWindow_cs/MW_Timer.cs	
@@ -61,8 +61,10 @@ namespace Ink_Canvas
         private Timer timerCheckAutoFold = new Timer();
         private string AvailableLatestVersion;
         private Timer timerCheckAutoUpdateWithSilence = new Timer();
+        private Timer timerCheckAutoUpdateRetry = new Timer(); 
         private bool isHidingSubPanelsWhenInking; // 避免书写时触发二次关闭二级菜单导致动画不连续
-
+        private int updateCheckRetryCount = 0; 
+        private const int MAX_UPDATE_CHECK_RETRIES = 6; 
         private Timer timerDisplayTime = new Timer();
         private Timer timerDisplayDate = new Timer();
         private Timer timerNtpSync = new Timer();
@@ -117,6 +119,8 @@ namespace Ink_Canvas
             timerCheckAutoFold.Interval = 500;
             timerCheckAutoUpdateWithSilence.Elapsed += timerCheckAutoUpdateWithSilence_Elapsed;
             timerCheckAutoUpdateWithSilence.Interval = 1000 * 60 * 10;
+            timerCheckAutoUpdateRetry.Elapsed += timerCheckAutoUpdateRetry_Elapsed;
+            timerCheckAutoUpdateRetry.Interval = 1000 * 60 * 10; 
             WaterMarkTime.DataContext = nowTimeVM;
             WaterMarkDate.DataContext = nowTimeVM;
             timerDisplayTime.Elapsed += TimerDisplayTime_Elapsed;
@@ -830,5 +834,92 @@ namespace Ink_Canvas
                 timerCheckAutoUpdateWithSilence.Start();
             }
         }
+
+        // 检查更新失败重试定时器事件处理
+        private async void timerCheckAutoUpdateRetry_Elapsed(object sender, ElapsedEventArgs e)
+        {
+            // 停止定时器，避免重复触发
+            timerCheckAutoUpdateRetry.Stop();
+
+            try
+            {
+                // 检查是否启用了自动更新
+                if (!Settings.Startup.IsAutoUpdate)
+                {
+                    LogHelper.WriteLogToFile("AutoUpdate | Auto update is disabled, stopping retry timer");
+                    return;
+                }
+
+                // 增加重试计数
+                updateCheckRetryCount++;
+                LogHelper.WriteLogToFile($"AutoUpdate | Retry check attempt {updateCheckRetryCount}/{MAX_UPDATE_CHECK_RETRIES}");
+
+                // 检查是否超过最大重试次数
+                if (updateCheckRetryCount > MAX_UPDATE_CHECK_RETRIES)
+                {
+                    LogHelper.WriteLogToFile("AutoUpdate | Maximum retry attempts reached, stopping retry timer", LogHelper.LogType.Warning);
+                    return;
+                }
+
+                // 执行更新检查
+                LogHelper.WriteLogToFile("AutoUpdate | Retrying update check after failure");
+                
+                // 清除之前的更新状态
+                AvailableLatestVersion = null;
+                AvailableLatestLineGroup = null;
+
+                // 使用当前选择的更新通道检查更新
+                var (remoteVersion, lineGroup, apiReleaseNotes) = await AutoUpdateHelper.CheckForUpdates(Settings.Startup.UpdateChannel);
+                AvailableLatestVersion = remoteVersion;
+                AvailableLatestLineGroup = lineGroup;
+
+                if (AvailableLatestVersion != null)
+                {
+                    // 检查更新成功，重置重试计数
+                    updateCheckRetryCount = 0;
+                    LogHelper.WriteLogToFile($"AutoUpdate | Retry successful, found new version: {AvailableLatestVersion}");
+                    
+                    // 停止重试定时器，因为已经找到了更新
+                    return;
+                }
+                else
+                {
+                    // 检查更新仍然失败，继续重试
+                    LogHelper.WriteLogToFile($"AutoUpdate | Retry {updateCheckRetryCount} failed, will retry in 10 minutes");
+                    
+                    // 重新启动定时器，10分钟后再次尝试
+                    timerCheckAutoUpdateRetry.Start();
+                }
+            }
+            catch (Exception ex)
+            {
+                LogHelper.WriteLogToFile($"AutoUpdate | Error in retry check: {ex.Message}", LogHelper.LogType.Error);
+                
+                // 出错时也重新启动定时器，稍后再检查
+                if (updateCheckRetryCount <= MAX_UPDATE_CHECK_RETRIES)
+                {
+                    timerCheckAutoUpdateRetry.Start();
+                }
+            }
+        }
+
+        // 重置更新检查重试状态
+        public void ResetUpdateCheckRetry()
+        {
+            try
+            {
+                // 停止重试定时器
+                timerCheckAutoUpdateRetry.Stop();
+                
+                // 重置重试计数
+                updateCheckRetryCount = 0;
+                
+                LogHelper.WriteLogToFile("AutoUpdate | Update check retry state reset");
+            }
+            catch (Exception ex)
+            {
+                LogHelper.WriteLogToFile($"AutoUpdate | Error resetting retry state: {ex.Message}", LogHelper.LogType.Error);
+            }
+        }
     }
 }
diff --git a/Ink Canvas/Resources/Icons-png/icc-dark.png b/Ink Canvas/Resources/Icons-png/icc-dark.png
index d682ec8c..c76d2373 100644
Binary files a/Ink Canvas/Resources/Icons-png/icc-dark.png and b/Ink Canvas/Resources/Icons-png/icc-dark.png differ
diff --git a/Ink Canvas/obj/Debug/net472/InkCanvasForClass.csproj.AssemblyReference.cache b/Ink Canvas/obj/Debug/net472/InkCanvasForClass.csproj.AssemblyReference.cache
index c8c2dfbd..57d842b8 100644
Binary files a/Ink Canvas/obj/Debug/net472/InkCanvasForClass.csproj.AssemblyReference.cache and b/Ink Canvas/obj/Debug/net472/InkCanvasForClass.csproj.AssemblyReference.cache differ