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Constant Prompting for Outlook Clients external to network with On-Premise Exchange 2007

Posted on 2013-12-15
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Last Modified: 2014-02-26
We have a Hybrid exchange solution with Exchange 2007 and Office 365 with on-premise Exchange 2013 hybrid server.

Steadily clients have been getting prompted for username and password when not onsite.  At first it was just a few now it is growing.

I have found some articles about Calendar.

All the clients are still on the Exchange 2007 server as we have not migrated anyone and some will stay on the Exchange 2007 box due to Call Manager.

Can someone point me in the right direction, it is obviously a authentication issue and they are coming through a Microsoft TMG 2010 firewall.

The outlook clients are a mix of Office 2010 and Office 2013 and both show same symptoms.

Thanks
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Question by:ITSystemSol
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Expert Comment

by:Will Szymkowski
ID: 39720261
When the users are correcting externally, using Outlook, what servers are they trying to authenticate to, you can check this with "Connection Status". Also are the users connecting using Outlook Anywhere, or are they connected to a VPN and still getting prompted?

Have you checked your TMG and viewed the logs to see if there is anything visible in the logs?

Will.
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Author Comment

by:ITSystemSol
ID: 39720574
I have had customer go through some testing scenarios.

They are authenticating against local servers to the site see screen sho ExternalClient.png attached.  Also under VPN connection there is no issue and I have attached a screen shot of the VPN connections status from outlook too ExternalClientVPNConnect.png.

There were errors in the Firewall logs when client was connecting to exchange from outside which I have put in attached PDF file.

This problem has grown, at first it was just random users but now more and more are experiencing the issue.

Thanks.
Firewall-Denies.pdf
ExternalClient.PNG
ExternalClientVPNConnect.PNG
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Accepted Solution

by:
ITSystemSol earned 0 total points
ID: 39876650
Deleted all the rules and then recreated the rules using a single Web-listener with both IP addresses added.
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Author Closing Comment

by:ITSystemSol
ID: 39888252
Nothing helped with resolving this except rebuilding the rules from scratch and recreating a new web listener.
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