Exchange Active Sync Fails After Transition From 2003 to 2010

The title sums this one up with ease. After transitioning / migrating from Microsoft Exchange 2003 to Exchange 2010 some of the first accounts that we tested with were unable to connect to EAS. Errors on the mobile client ranged from server not found/available, to bad user name and password errors. After much research and troubleshooting I came across a few users that were experiencing the exact same issue. You can read more about the issue and the fix here.


Recreate OWA Virtual Directory IIS7 / Exchange 2007

Ran into an issue today where a clients SBS 2008 server stopped servicing requests made to hostname/owa. I am still unsure as to what caused this issue but find a fairly simple way to recreate the OWA virtual directory for IIS. Many admins are familiar with this procedure / howto for Exchange 2003 but are unable to find something similar for Exchange 2007. While the step that I will describe below is not as in depth as the previous link, it did resolve my issue.

If your OWA is giving you the dreaded 404 treatment try this: Open IIS Manager and delete the OWA virtual directory. Next you will need to open the Exchange Management Shell. Enter in the following command and press enter afterwards: New-OWAVirtualDirectory -OwaVersion:Exchange2007 -Name "OWA" .

That will rebuild / recreate the OWA virtual directory and start accepting client requests immediately. Please note that this recreates the OWA virtual directory under Default Web Site, not under SBS Web Applications like a default SBS / Exchange 2K7 install.

Hopefully, this one liner will save you some trouble.


Exchange Outbound SMTP Smart Hosting

There are countless situations in which you might not want to send email via SMTP directly from your site. Maybe you aren’t familiar with PTR’s and A records, or maybe your IP has been blocked / banned via your ISP or some external RBL. If your mail host allows you to use their server as a smart host, you can avoid most of these worries. Up until recently most mail traveled to and from servers and clients using the SMTP protocol which runs on 25 (TCP). Several mail hosts and ISP’s are now requesting or flat out requiring that the mail be submitted to their servers using the more modern mail submission port which is 587 (TCP). For more information on this please see this link. In order to successfully complete this how-to, you must get in touch with your mail host and see which port they want mail submitted on.

I will use port 587 in this example since this is what my mail hosting company requires.

Step 1: Configure Exchange to use the desired port

Open up the Exchange System Manager and expand Servers, Your Server, Protocols, SMTP. Expand SMTP and right click / properties on the Default SMTP Server. Go to the Delivery tab and then click on Outbound Connections. The last box is the port that Exchange is currently configured to send mail on. Once again, for my mail host port 587 is required. Click OK until you get back to main window of Exchange System Manager.

Step 2: Create an SMTP Connector to route mail

Right click on the Connectors folder and choose New -> SMTP Connector. Name the new connector and then choose the option to “Forward all mail through this connector to the following smart hosts.” Now enter in the hostname provided to you by your hosting company. This is usually the same as the outbound mail server that you would configure in your mail client. Under local bridgeheads click add. Select your Exchange server and click OK. Next, select the Address Space tab and click add. Choose SMTP and click OK. Leaving the default email domain of * and the default cost of 1 should be sufficient depending on your Exchange configuration. Click OK after confirming these defaults.

From here we need to configure outbound authentication. Select the advanced tab and click on Outbound Security. Click on “Basic authentication password is sent in clear text” and then click Modify. Enter in the username and password that was given to you by your mail host. Hit OK until you are back down to the main Exchange System Manager window.

Step 3: Verify the configuration

Start by going to start run and typing in services.msc. Locate the Simple Mail Transfer Protocol server and restart it. Now open up Exchange System Manager again and expand Servers, Your server name, Queues. Send a few test email messages from a client machine and watch the queues. If you see domains that were recently sent to showing a ready state all should be well. If you see domains that have a retry status and messages piling up there is an issue somewhere. Go back through all of the settings mentioned above and look for typo’s, misspellings, and other possible obvious points of failure in the configuration. Double check with your mail host and be sure that you are using the correct information.

NOTE: After correcting any issues found, right click on the failed queues and try forcing the connection. It is sometimes necessary to right click each domain and find messages and then delete them.