Free tool tests connectivity to your Exchange environment

Scott Lowe demonstrates Microsoft's free tool that tests and helps you troubleshoot remote connections to Exchange.

Getting that new Exchange 2010 environment fully operational and providing services to all manners of devices is no easy task. It takes a lot of planning and a lot of cooperation between teams, including the systems team and the team that handles poking holes in the organization's firewalls. After all, that communication from things like mobile devices using ActiveSync and external computers using Outlook Web Access has to get to Exchange somehow, right?

But, there's a lot more to it than just getting the firewall settings correct. You must have properly configured internal and external URLs in Exchange and procured an appropriately configured SSL certificate for the environment.

Even with the best planning, execution can sometimes throw a monkey wrench into the works and tracking down external connectivity problems can be a real bear. Fortunately, Microsoft provides a free tool that will tell you exactly where you need to start looking in your troubleshooting efforts. This tool, called the Microsoft Remote Connectivity Analyzer, can save you hours of frustration and runs through all of the possible connectivity methods at your disposal so that you can see exactly how communications are taking place.

For some, there will be a downside; you need to provide the Remote Connectivity Analyzer with a username and password in your environment that is valid. This will cause concern for the particularly security minded. So, if you're concerned that Microsoft may misuse this information, don't use the tool. However, for what it's worth, here's a look at the security chain for the site:

Figure A

The site's security certificate chain
When you get to the Remote Connectivity Analyzer site, you're going to notice that there are a whole lot of connectivity options (Figure B). You can test internal Exchange servers and can also test any services that are hosted at Office 365. I've used the Exchange testing items for my example even though my domain is hosted at Office 365.

You can test a number of different use cases, including ActiveSync connectivity, web services connectivity, Outlook Anywhere connectivity, and SMTP.

Figure B

ExRCA home page
Once you've decided in the type of test you'd like to perform, you're asked for a few pieces of information. These would be the same pieces of information you're asked if you want to set up a new account on a mobile device or you want to use Outlook Web App. You can also choose whether or not to sync the contents of your inbox as a part of the test to make it a bit more thorough. You'll also see in Figure C that you need to provide a password for the account you use as well as a CAPTCHA code. In this example, I'm testing ActiveSync.

Figure C

Provide the information required to run the test.
While the test is running, you'll get a screen like the one shown in Figure D.

Figure D

The test is underway.

Once the tool completes its work, you've presented with an extremely detailed report that outlines every success and failure encountered by the tool. In many cases, there are multiple ways for a device to access an Exchange server so, while one connectivity option may fail, another may succeed. As long as the end result is achieved - the device is able to connect - this is treated as a success even if some connectivity options fail.

In Figures E and F, you can see that some connectivity methods did not work, but as you drill down, you get to see exactly where the process went awry. This makes it simple to determine where to begin additional troubleshooting efforts.

I've included these two screenshots because they show you both success and failure and let you see just how much information you can get from the tool.

Figure E

Some tests succeeded while others failed.

Figure F

Success all around


If you're responsible for your Exchange environment, you need to keep this tool at the top of your list.

By Scott Lowe

Since 1994, Scott Lowe has been providing technology solutions to a variety of organizations. After spending 10 years in multiple CIO roles, Scott is now an independent consultant, blogger, author, owner of The 1610 Group, and a Senior IT Executive w...