Restart Outlook, and then try sending or receiving email. Step 2: Empty the Outlook send folder Open the Send folder in Outlook, and then delete all messages that are listed there. If there is a check mark, click Work Offline again. Click the Outlook menu, and see whether the Work Offline option has a check mark. It will go into the Microsoft Database Utility mode where you can rebuild the Identity (Database).Press the Option (Alt) key while clicking on Outlook to open it.Backup (or copy) your Office 2011 identities folder located in “~/Documents/Microsoft User Data/Office 2011 identities/”.Kill all Microsoft Office applications processes (i.e.To do this you can follow these instructions from Microsoft: To summarize: The Database for the Outlook profile can get corrupted over time and may need to be rebuilt on Outlook 2011 on Mac. So there is a potential fix for most of you out there. It is sad when your phone becomes the more reliable email client. I occasionally have the issue of my Outlook either crashing and then it won’t sync my mail in outlook.