Outlook Anywhere fails to connect
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Saturday, May 19, 2012 3:58 AM
I have SBS 2008 with Exchange 2007 operating since 2009.
Outlook Anywhere was configured on several remote PCs (XP SP3 and Win7) two years ago. The setup procedure was followed precisely, including the installation of the certificate on each PC. Outlook Anywhere connections to our Exchange server has worked continuously since setup.
Today Outlook reports access to the Exchange Server is unavailable for all remote users.
Attempts to access https://remote.domainanme.com/remote reports a certificate error.
Exchange Management Shell "GET-EXHANGECERTIFICATE" reports that its service certificates expired today and are no longer valid.
Using the management shell I renewed the certificates on the server, but remote Outlook still reports the Exchange server is unavailable.
The server remote sub-domain name is pingable, and email access works fine via OWA and ActiveSync.
Your ideas would be greatly appreciated.
Thanks,
Ken
Ken
All Replies
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Saturday, May 19, 2012 4:38 AM
Ken,
The fastest way to fix the issue is to run the Connect To Internet Wizard, The Internet Name wizard, and the Install a trusted certificate wizard. If you are not choosing to install a certificate from a Trusted root authority, you will aslo need to install the the self signed cert on the client machines, which can be found in .\public\downloads.
You need to run the Internet name wizard to create the self signed cert, and you must use the trusted certificate wizard so that all parts of Exchange and IIS including remote Web Workplace work properly.
Thanks
Jeremy
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Sunday, May 20, 2012 8:32 PM
Thanks Jeremy.
I had to abort the Connect to Internet Wizard, since it could not detect the router and found DHCP servers on other subnets. Also I should have stated that SBS 2008 is running in a VM under a Win 2008R2 host, which is in a physical network that is shared with other subnets - one for SBS 2003 and another for VOIP.
Is there a manual procedure that I could use to create the self signed certificate, assuming I could then run the trusted certificate wizard and manually distribute the certificate installer?
Ken
Ken
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Monday, May 21, 2012 3:44 AM
Can you run the "Set up your Internet Address" wizard or does it force you to run the "Connect to internet wizard first"?
With SBS, the only SUPPORTED way to renew that cert is the "Set up your Internet Address"
You can add a "real" trusted cert from GoDaddy by only running the "add a trusted certificate wizard".
BTW - unrelated to this issue, but if your SBS server can see DHCP servers in other subnets, you have multiple colision domains, and your network probaly runs like a 20 year old Chevy. Poorly, that is.
Jeremy
- Marked As Answer by James XiongModerator Monday, May 28, 2012 12:52 AM
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Monday, May 21, 2012 8:09 AMModerator
Hi,
So what’s the error message you have received when you try to use the Microsoft Remote Connectivity Analyzer to test the Outlook Anywhere?
You could use the following tool to do the test:
Title: Microsoft Remote Connectivity Analyzer
URL: https://www.testexchangeconnectivity.com/After testing, please post back the result here to get further analysis.
Regards,
JamesJames Xiong
TechNet Community Support
- Marked As Answer by James XiongModerator Monday, May 28, 2012 12:52 AM
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Monday, May 21, 2012 12:48 PM
The Outlook Anywhere test failed Certificate Trust Validation, presumably because the (self-signed) certificate I created on the exchange server has not been installed on my test PC.
I understand that installing a trusted CA certificate at the SBS server is the simple solution, but my management is not willing to pay for it.
Ken
Ken
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Monday, May 21, 2012 4:13 PM
A "real" certificate cost ~$20 USD. You need to be able to run the "Set up your Internet Address" to create and install a new Self Signed cert. If you can not run that, you need to fix the condition that prevents you from running the Wizard.
Does the Test Exchange Connectivity Wizard Complete Successfully if you choose to ignore Certificate Errors? What is the Exact Error you recieve?
Jeremy
- Marked As Answer by James XiongModerator Monday, May 28, 2012 12:52 AM

