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outlook clients can't connect to new exchange 2013

Posted on 2013-12-15
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Last Modified: 2013-12-16
We've just migrated from sbs2008 to server 2012 standard and exchange 2013. Exchange 2013 is up and running. OWA access is up. Activesync is working as well, as smartphones are connecting successfully. The problem still left is outlook clients. Curiously enough, mac outlook clients seamlessly made the switch and are sending/receiving. Outlook on windows however is another story. I did read that outlook and exchange 2013 now require an outside ssl cert, no more self signed. We had an external cert already, and I attempted to export/import it and continue to use it. Outlook complains that the server names don't match, so I've submitted a re-key request. I understand that could be part of the dificulty. When I try to connect an outlook client, autodiscover responds and tells me of the certificate issues, but I accept anyways. After entering the username/password, "finding server settings" reports as successful, but then "log on to server", I receive the error "The action cannot be completed. The connection to microsoft exchange is unavailable. Outlook must be online or connected to complete this action." This is repeatable from multiple pc's, outlook 2007, 2010, 2013. So my question, is this solely related to the SSL certificate issue, if at all? How do I discover my connection settings, so as to manually configure outlook, to make sure autodiscover isn't the problem? What is different about the way mac outlook connects that allows it to work so easily?
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Question by:sdholden28
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Author Comment

by:sdholden28
ID: 39720840
Outlook then prompts for Microsoft Exchange Server and mailbox
For exchange server, it is populated with the below, presumably from autodiscover:
5e5dc123-77a0-4278-83de-e72e9a5fd20e@domain.com

For mailbox:
=SMTP:2013test@domain.com

2013test is a valid mailbox with owa and activesync working.

I obviously don't know, but those addresses do not look right to me. I have followed the self issued method detailed here, outlook can't connect, but to no avail.
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Accepted Solution

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Simon Butler (Sembee) earned 500 total points
ID: 39720996
That is classic Autodiscover not working problems.
If you have a trusted SSL certificate in place then you need to ensure the host name on the trusted certificate resolves internally to Exchange and the URLs are changed within Exchange to match.

I need to write an Exchange 2013 version, but my Exchange 2010 article shows what needs to be done via Powershell.
http://semb.ee/hostnames

Don't try and use a self signed certificate, that will give you nothing but headaches.

Simon.
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Author Comment

by:sdholden28
ID: 39721280
Thanks. I'll have a look. In the meantime, how can I discover the settings for manual outlook config? Simple I'm sure, just never had to do it.
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Expert Comment

by:Simon Butler (Sembee)
ID: 39721784
You can't use manual configuration with Exchange 2013, because each user has a unique end point (the GUID you see) which means it needs to be returned by the Autodiscover system.

Simon.
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Author Comment

by:sdholden28
ID: 39722171
Excellent article on the autodiscover setup. I've got my certificate sorted and outlook clients are connecting easily. Thanks very much for that.

I've got another issue thats popped up I'm trying to sort that I think is related. Iphone/android users. Autodiscover works sometimes, sometimes it doesn't, even on multiple account setup attempts from the same device. I have some users whose email setup verifies on an iphone right from the start, on any device and works well. I have a handful of users who can setup their account, and it gets "verified", but then when you open the mail app, it says cannot connect to serve. IOS version does not seem to matter, and I've done the simple things... remove account, power cycle device, verify username and password with OWA, etc. Any ideas on where I should look? I'm trying to compare the user accounts between working users and non, but I have found any differences yet. Thoughts?
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Author Comment

by:sdholden28
ID: 39723146
Thanks again for the tip on the dns. This link has the solution for the ActiveSync issues. http://eightwone.com/2011/08/31/exchange-activesync-and-inheritable-permissions-issue/
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