Outlook2011 for Mac and Exchange

Dear Experts,

I seem to not be able to connect Outlook 2011 for Mac to our Exchange.
Initially, it makes connection, it syncs all folders, then stays on.
The next time I open it, it gives me an error saying that it failed to log in.
It asks to reenter my password, which I keep in my Keychain, but it will never connect again until I remove the account and recreate it.
I have also reset my Keychain, tried without SSL, tried giving the IP address of my Exchange Server, etc.  None of them work.
I just downloaded Outlook 2011 with Service pack 3 from Microsoft Volume Licensing Center, so I am assuming that this is the latest copy.
This Mac is brand new, and just did an update on OS.  What else can I do to get this resolved?
Please advise.
yballanAsked:
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yballanAuthor Commented:
Just as an additional note, I  have tried it with different accounts, and the behavior is the same.
Also, OWA on this Mac for the same account works fine.
thanks.
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Jian An LimSolutions ArchitectCommented:
Frontend

how do you save your user/password?
do your username in user@domain.com format or domain\user format?
change the format and see whether it replicate the same issue?



Backend reset

Remove-WebServicesVirtualDirectory -Identity "server\ews (Default Web Site)"
New-WebServicesVirtualDirectory

After that, please perform IISreset /noforce on the server and try again.
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yballanAuthor Commented:
Dear limjianan

Thank you for your response, I use  domain\user format.
Are you referring to setting up the account on the Mac, or in Outlook?
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yballanAuthor Commented:
OK, I tried it with both.
if I use username@domain.com, it does not let me finish setup at all.
if I use domain\username, it will let me finish, then I get this error,
"Mail could not be received at this time."
Please see attached.
I can use the same login info and log into OWA from this Mac.
Screen-Shot-2015-04-21-at-11.35.42-AM.pn
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yballanAuthor Commented:
Before I do the Backend Reset, will this affect the existing PC users with Outlook 2010?
We have about 70 PC users, and only 2 Mac users.
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Jian An LimSolutions ArchitectCommented:
Before doing a backend reset,

can your mac access  the below website without issues (with keychain)?
https://webmailname/EWS/Exchange.asmx

The reason i want to know is whether keychain works well with the encryption model of the server.
what windows are your exchange on at the moment?



So for doing a backend reset,
Outlook 2010 use EWS on out of office/rules and etc so it might impact these function in a short period of time. But fundamentally it won't break Outlook 2010
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yballanAuthor Commented:
I've requested that this question be deleted for the following reason:

Found out that autodiscovery was an issue and disabled it.
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Jian An LimSolutions ArchitectCommented:
if you believe the answer is autodiscover, then accept your own answer rather than delete it
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yballanAuthor Commented:
disabling autodiscovery using Apple ScriptEditor fixed the issue.
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