Yosemite vs Exchange

Customer recently upgraded to Yostemite. Now his mail client doesn't work right. He is connecting to an exchange server. After rebooting the machine, the first time he opens Mail it will update and sync. Then after "a bit," which I'm unsure of how long because he didn't tell me, it will no longer update. Today when I got on the machine his last update was at 10am.
On top of that, when he first boots the machine up, his OWA site is inaccessible. It later becomes accessible, and then goes back to not existing to his machine.
He is one of two macs in his office, with the 2nd one having no issues. I was unable to get access to the 2nd machine to verify settings.
No one else is having any issues. I have full access to the OWA site, and even logged into it on my computer so I know it's not password related.
I've unchecked the automatic settings, but was not able to rebuild his profile as he was mad that I was working the mail app issue and not the OWA issue. He was certain it was a problem with the server.
I'm lost, and I can't find anyone have the exact same issue. I've given basically as much detail as I have, and the customer has gone home for the day and I no longer have access to the computer for this evening.

For a while it seemed like Internet Accounts pane of System Preferences was altering my exchange server public address.  I had to manually change it for several days and each day several times a day.
Ultimately I checked the box for 'Enable this account' and turned off my exchange account, and then turned it back on.  Now my settings have stuck. 
What you describe here sounds to me like connectivity issues due to login credentials.  You can also run Connection Doctor to see what that says.
Hope this helps.

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    Best regards,
    Damian

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    Apple doesn’t routinely monitor the discussions. These are mostly user to user discussions.
    Send Apple feedback. They won't answer, but at least will know there is a problem. If enough people send feedback, it may get the problem solved sooner.
    Feedback
    Or you can use your Apple ID to register with this site and go the Apple BugReporter. Supposedly you will get an answer if you submit feedback.
    Feedback via Apple Developer

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    Hi,
    Since Outlook running on Windows works well, it seems an issue on the Mac side. I suggest ask Mac for help so that you can get more professional suggestions.
    More information for your reference:
    Please try to verify whether there is any expired certificate from the computer personal store.
    If it is the case, please remove them.
    Thanks
    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact [email protected]
    Mavis Huang
    TechNet Community Support

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