Note: If you're running a 32-bit version of Outlook on a 64-bit version of Windows, you'll need to add these registry keys in the correct location for 32-bit applications. HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\ReceiveTimeoutSeconds > DWORD Value = 00000600.HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\SendTimeoutSeconds > DWORD Value = 00000600.HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\ConnectTimeoutSeconds > DWORD Value = 00000030.HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\ResolveTimeoutSeconds > DWORD Value = 00000030.Add the following keys to override the default timeout values: You can extend this period by modifying your Windows registry. By default, the timeout is hard-coded to occur at 90 seconds. The message remains unsent in your Outbox. If you send a message with large attachments over a slow connection, the connection can time out.