This article describes the steps for troubleshooting connectivity issues in Outlook 2011/Outlook 2016 for Mac.

Before proceeding check if you can log in to Webmail (OWA). That will allow you to determine if your connection to the server works fine.

Make sure that Outlook is in Online state

Go to Outlook > Tools and switch it to Online mode if it is Offline.

Online State

 

Check identity configuration

Open Outlook and go to Tools > Accounts, select the existing Exchange account, and click the Advanced button in the lower right-hand corner of the window.

 Tools

Settings

For more information read the article on Outlook 2011 For Mac Setup Instructions.

 

Run traceroute command in Terminal

This troubleshooting step allows you to determine if your connection to the Exchange server is lost, and also shows where exactly that happened.

Go to Applications > Utilities > Terminal to run the command.

  • If timeouts happen at the very beginning of the route, reboot your network equipment or contact ISP.
  • If you see asterisk signs at the end of the route contact Support. Note that some servers might reject ping requests so timeouts on one particular hop do not indicate an issue.

traceroute

Read the Knowledge Base article What Is A Trace Route (tracert)? How Do I Run One? for detailed instructions. 

 

Remove corrupted entries from Keychain

If you receive the error Mail could not be received at this time clear credential entries from Keychain:

Go to Applications > Utilities > Keychain Access and find entries for Exchange credentials. Right-click an entry and click Delete, then confirm the deletion.

After you do that run Outlook and enter your password to create a new entry in Keychain.

Keychain

Outlook 2011 Custom Contact Categories

Issue:

Custom contact categories created in Outlook 2011 do not synchronize properly with Outlook for Windows or Outlook Web Access.

Details:

Within Outlook for Windows or Outlook Web Access, users opening contacts linked to custom categories originally created in Outlook 2011 will observe blank colors with the suffix "(not in Master Category List)".

Workaround:

Within Outlook for Windows users can open these contacts and go to Categorize > All Categories > highlight the blank custom category > click on New > choose a color > click OK. This previously missing category now appears in the Master Category List across both Outlook for Windows and Mac. If users now categorize/uncategorize contacts within Windows/Mac the changes will synchronize between Windows/Mac. This custom category is also now searchable in Outlook for Windows.

References:

Compare Outlook for Mac 2011 with Outlook 2010 for Windows

Outlook 2011 - Sharing a folder the option "Folder Visible" stays unchecked

Issue:

Users refer to "Grant access to your Inbox, subfolders and custom top-level folders without Sharing invitation" in article https://hosting.intermedia.net/support/kb/viewKBArticle.asp?id=720, but within Outlook 2011 in steps 5 to 7 the "Folder Visible" box does not stay checked.

Workaround:

A workaround is to select 'Own' under "Edit Items:" in addition to checking "Folder Visible". Finally, the user may go to Open > Open User's Folder. Please enter the name of the user, select folder type as Inbox and click OK. The Inbox of the other user will appear, but it should be blank. The user should now have access to the subfolder based on given permissions.

Outlook 2011 for Mac known issues