Identifying Outlook Anywhere connectivity glitches
Outlook Anywhere connects users to Exchange Server using an Outlook client outside their
perimeter network. This is accomplished by encapsulating Outlook-related traffic within HTTP
packets. Outlook Anywhere's initial configuration is pretty tricky and connecting might be tough,
but it shouldn't be much trouble after you're up and running.
If you can't connect to Outlook Anywhere, the first thing you should do is run the Exchange Remote Connectivity
Analyzer (ExRCA). The ExRCA is a Web-based tool that diagnoses various types of Exchange Server
2010 connectivity issues.
To begin testing your connection with Exchange Server, choose the Outlook Anywhere (RPC over
HTTP) test. Click Next
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This was first published in May 2011
and you'll be prompted to enter an email address as well as
credentials that specify you're accessing a mailbox on Exchange (Figure 1).
Figure 1. You must provide the ExRCA with proper credentials before testing Outlook Anywhere
connectivity.
ExRCA will run through a series of tests to determine whether or not Outlook Anywhere is
connected. When the tests complete, you will see a screen similar to the one in Figure 2 that shows
if the test passed or failed.
Figure 2.This is an example of ExRCA test results.
This screen doesn't immediately explain why the test failed. It only indicates that Outlook
Anywhere isn’t working. To find out why the test failed, click Expand All and ExRCA will
display a list of each test that was performed as well as the results (Figure 3).
Figure 3. You can view detailed information on ExRCA tests and results.
In this example, several tests failed. The first bullet points indicate the failure occurred
because of an SSL-certificate issue. I’m using an SSL certificate that an in-house certificate
authority (CA) generated; the server ExRCA runs on doesn’t trust the CA.
If you're using an in-house CA and receive this error message, it doesn’t necessarily mean that
there is a problem. But you should verify that client computers connecting to Outlook Anywhere
trust your CA. You should also make sure your client
access server (CAS) isn’t configured to use a self-signed certificate.
If you’re trying to determine why an error occurred, the Tell Me More About This Issue and
How to Resolve It link can be helpful. This ExRCA component, which is located next to each
individual error message, directs you to a TechNet article explaining how to fix the issue.
Configure Outlook clients for Outlook Anywhere
After you've properly configured Exchange Server, you’ll want to configure Outlook clients to use
Outlook Anywhere. If you're using Outlook 2010, navigate to the File menu and click
Info and then Account Settings. Click the Account Settings option and then
double-click on the listed account. Next, select More Settings and navigate to the
Connection tab.
Outlook 2010 is configured to connect through a local area network (LAN) by default (Figure 4).
Select the Connect to Microsoft Exchange Using HTTP check box and use the Exchange Proxy
Settings button to specify a proxy URL and authentication method.
Figure 4. For Outlook Anywhere to work, Outlook must be configured to connect to Exchange over
HTTP.
Commands to test Outlook Anywhere connectivity
You can also use Exchange Management Shell (EMS) cmdlets to test Outlook Anywhere connectivity,
specifically the Test-OutlookConnectivity cmdlet. While ExRCA tests external Outlook
Anywhere connections, EMS tests connectivity within your perimeter network. If an external test
fails but an internal test succeeds, you likely have either a DNS issue or firewall problem.
Before using the Test-OutlookConnectivity cmdlet, Microsoft recommends that you create a special
test mailbox. If you ran the Test-OutlookConnectivity cmdlet against one of your own mailboxes, the
cmdlet could fail because of an improperly configured or damaged mailbox. Using a test mailbox
means test results are based on the CAS configuration.
To create a test mailbox, open the EMS and go to \Program Files\Microsoft\Exchange
Server\V14\Scripts. Next, run the following script ./New-TestCasConnectivityUser.ps1.
You may have to modify your execution policy using the Set-ExecutionPolicy cmdlet to run the
script.
After the script runs, create a password for the test mailbox. Then test your Outlook Anywhere
instance using the following EMS command:
Test-OutlookConnectivity –Protocol:HTTP –Identity:Extest_F727e8cb68fc4
–MailboxCredential(Get-Credential lab\extest_f727e8cb68fc4)
–GetDefaultsFromAutoDiscover:$true
Enter the test mailbox password and the cmdlet will run through a series of tests to verify that
each Outlook Anywhere component is functional.
ABOUT THE AUTHOR:
Brien Posey is a seven-time Microsoft MVP with two decades of IT experience. Before becoming
a freelance technical writer, Brien worked as a CIO for a national chain of hospitals and
healthcare facilities. He has also served as a network administrator for some of the nation’s
largest insurance companies and for the Department of Defense at Fort Knox.
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