Hi Alison,
To better help you with this issue, I’d like to confirm the following information:
1. Regarding the following article: Install Office using Office 365 for business, whether you’re using Outlook for Mac for Office 365 or Outlook for Mac 2011?
2. Can you enter the logging page? If yes, please capture some screenshots to show how the issue occur.
3. Capture a screenshot of the “Offline Mode” Outlook for Mac.
4. Provide us with the detailed steps or screenshots when you re-activating the Outlook installation.
To upload screenshots, you can click Use rich formatting in the forum and then click the icon of Insert Image.
With the information requested above, we will provide assistance based on your exact situation.
Best regards,
Rachel Zhang