Whenever you get the message 'The connection to Microsoft Exchange is unavailable' you can use the Exchange Remote Connectivity Analyzer to analyse and test Exchange connectivity.
Email is the lifeblood of businesses today. Everyone needs email access and they need it everywhere, in the office, at home, at the airport and in the motel room where they’re meeting their lover. Maybe that last one is stretching it a bit but email connectivity from everywhere and on every device is certainly a top priority for many Exchange administrators.
Fortunately Microsoft provides an online tool to help troubleshoot remote connectivity that has steadily improved over the years; the Exchange Remote Connectivity Analyzer
Exchange Active Sync
The first two tests on the main screen are related to mobile devices. There’s a test to make sure your Autodiscover DNS records are published correctly in DNS and available from the internet. There’s also a test to verify connectivity to your Exchange Active Sync server (Client Access Server role).
You have to specify the server (or use Autodiscover), a valid username and password as well as acknowledge that the details you provide are valid. All the tests ran fairly quickly in my testing.
It gives me peace of mind to run through a few of these tests before telling the client “yes – your new shiny smartphone will work just fine with email”.
After making sure people can get their emails, calendars and so forth on their mobile devices it’s almost as crucial to make sure their Outlook “just works” no matter where they are. Notwithstanding newer technologies such as Direct Access; Outlook Anywhere / RPC over HTTPS is an anchor for many a road warrior armed with a laptop.
Again you have to specify an email address, username and password and either use Autodiscover to find your server or manually enter the details. If you do enter the server details manually make sure to leave the https:// bit out of it.
SMTP In and Out
Perhaps more crucial for you as an administrator than the above user-centric access methods is basic mail flow in and out of your organisation. While you can always test SMTP mail with a Telnet session (see here for instructions) this can be laborious so this test is quicker.
All that is required is an email address for the inbound test, if all goes well a test email shows up in your inbox.
For the outgoing test you’ll need to provide the IP address of your outgoing email server as well as an email address. It’ll also do a reverse DNS check, a block list check (RBL) and a Sender ID check.
For those times when you’re tearing your hair out, trying to figure out why it’s not working when it should be, the Exchange Remote Connectivity Analyzer can be your hair’s best friend. Similar tests can be done elsewhere (http://www.mxtoolbox.com for instance) but nothing is as specifically geared towards Exchange as this tool.