Mac For Outlook 2016 Sync Error

In my last post, I covered an error message I received randomly on mac os. After fixing the issue, I noticed that Outlook was behaving oddly including:

Try deleting the Exchange account from Outlook and recreate it. Sometimes this solve the problem with Exchange sending/receiving/sync issues. I have troubleshot various Outlook 2016 on MAC connecting to Exchange 2016/Office365 Exchange and the only pattern to the problem is that they started after the latest OS update. I'm running Outlook for Mac Version 15.37 on OSX 10.11.16. For the past couple of weeks I've had this issue with attempting to send emails. It only occurs sporadically. I get several sync errors and the email I'm trying to send gets hung up in the Outbox. When I go to the Sync Errors menu I get the following messages. See image below.

  • Calendar was not updating
  • All Calendar invites/updates/removals arrived as empty messages
  • Any time I deleted an email it would shortly reappear in the same folder
  • If I selected a message that had reappeared, it would magically disappear shortly thereafter

In Outlook, click Help Check For Updates. If an update is found, download and install it. Restart Outlook. If the problem continues, click Help Contact Support.

What was going on? Read on to learn more!
This time I could easily check the logs so I did, but unfortunately they did not report any issues. I, of course, ensured I was running the latest version of Office and then did what Microsoft typically recommends — manually uninstall and manually reinstall Office for Mac 2016. Unfortunately, this process is not as user friendly as I hoped (see here for more details) and requires you to manually delete the following:

  • All Office applications in the Applications folder
  • The following Library containers: ~/Library/Containers/com.microsoft.*
  • The following Library group containers: ~/Library/Group Containers/UB*

Finally you need to restart the computer. After completing this, I reinstalled Office, but the problem persisted. Next up, I enabled troubleshooting logging. To do this, you go to Tools > Sync Errors > Gear Icon > Turn on logging for troubleshooting. Then you need to close Outlook and open it again — wish it would state that. Then you reproduce the issue and check the logs — the big question is where are the logs? Unfortunately, Outlook does not tell you this either, but you can find it in: ~/Library/Containers/com.microsoft.outlook/Data/Library/Logs. Tailing this log while reproducing the issue will result in a lot of output. What I eventually realized is that you need to look for messages that contain the word “Unexpected” — Microsoft would it kill you to adhere to syslog RFC standards is use something like “error”? — note using grep on the file did not work for me so I used vim and its search capabilities to look for Unexpected messages. The first set of Unexpected messages I received looked like the following:

A quick Google search did not turn up much on the error or the errorCode so I decided to keep looking. The next one looked promising:

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A bit further down I saw:

OK, I see a file IO error, an error code and a message about failing to create a temporary directory. What critical piece of information am I missing? Yup, the filename and/or filepath. Remember kids, log messages are only as good as the information that they contain!
Well, I know I had permission problems with my home directory given my previous blog post, but I also know that I fixed them. mac os Sierra does not allow repairing permissions because the system files and directories cannot be modified. Even if they had been modified, reinstalling mac os would have resolved this issue as well. So, where is the permission problem? After digging around the filesystem for a bit and turning up nothing, I decided to create a new user account, install Outlook and see if I could reproduce the issue there — wouldn’t you know it worked without issue. This was a strong indication that the problem was with my profile, but I had confirmed — multiple times now — that the permissions on my profile were correct. Then I remembered TMPDIR.
You may remember my note in my previous blog post where I stated that I checked /etc/passwd to double-check my User ID, but could not find the entry. Just like mac os uses a non-Linux standard directory service utility, mac os uses TMPDIR which provides a user specific private temporary directory space in /var/private. You can echo the variable to see the location:

Wouldn’t you know this space has an Outlook directory:

and look at that, it is owned by root. I changed the permissions recursively on this directory:

and all my Outlook problems went away! (Note: Remember to turn off troubleshooting logging in Outlook)
I still do not know what was responsible for changing the permissions on my files and directories, but I do know I wasted a bunch of time because:

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  • Default error logging was not sufficient
  • Debug error logging was hard to turn on and the log file was hard to find
  • The log file did not use standard terminology for reporting errors, used codes that were not defined, did not support normal CLI commands such as grep, and did not contain critical pieces of information such as filepath

Outlook Mail Sync Error

The morale of this story? Logging is important; make logging easy, follow common standards and include relevant pieces of information.

© 2017, Steve Flanders. All rights reserved.

Fix authentication failed errors in Outlook 2016 on Mac.

4th July, 20174th July, 2017

Applies to: E-mail, Web Hosting

Difficulty:EasyTime needed:5 minutesMac For Outlook 2016 Sync ErrorRequired:Ecenica Email Settings, Outlook 2016 for Mac

Problem

When you access your email in Outlook 2016 for Mac the following error can occur:

Mail could not be received at this time The server for account “example” returned the error “[AUTHENTICATIONFAILED] Authentication failed.” Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

Symptom

  • When you open or send and receive email from Outlook 2016 for Mac the error is shown.

Mac For Outlook 2016 Sync Errors

Cause

Mac For Outlook 2016 Sync Error

Outlook 2016 cannot connect your email account because the username or password it is using is incorrect.

Mac for outlook 2016 sync error download

Resolution

Check your email password is correct and you are using your full email address, for example. info@example.com, for the username in your Outlook 2016 settings.

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Outlook Email

Screenshot of Error