We have had several staff run into a situation where Outlook is not sending or receiving new messages and shows an error whenever it tries to do a "Send/Receive". This is occurring because Outlook is in "Work offline" mode. This happens if you press "Cancel" on the screen where you are being asked to provide your password to Google Apps Sync.
How can you tell if Outlook is in “Work offline” mode? Your new messages won’t show up and you will get an error when Outlook tries to do a “Send/Receive”. Also, the Outlook icon in the system tray will be gray with a red checkmark in the middle of it. The Google Apps Sync icon will also be gray instead of the usual green.
How can you get Outlook back online? To get out of offline mode you just need to go to the main Outlook screen and click “File” on the main menu. You will notice a checkmark next to the “Work Offline” menu option. Click on “Work offline” to toggle into online mode. In a couple seconds a dialogue box should pop up asking for your email login credentials.