Using the Microsoft Connectivity Analyzer Tool

Reading Time: 4 minutes

imageRecently Microsoft released an updated version of the Microsoft Exchange Remote Connectivity Analyzer rebranding it as the Microsoft Remote Connectivity Analyzer as it now also can test Lync connections, next to Exchange and Office365.


Another addition is the Microsoft Connectivity Analyzer Tool, a local variant of the online tool for Exchange connections. This is a very helpful tool for internal testing and despite being in beta, it already successfully helped me correctly identifying a certificate issue before I used it in production.

As it is a local tool, it uses your local DNS and network routing. As said this is helpful for local troubleshooting as sometimes the connectivity is different from (for instance public Wi-Fi networks) than the external connection. But another effect of this that you can use it in lab and testing environments before making changes final. In my case we did not yet change external DNS A-records to point to the new Exchange 2010 datacenter, everything else was already set up for publishing. By changing my local host file I could test the new datacenter with the correct domain name as if it were in production.

I already detected an issue with the Outlook AutoDiscover process, and however the Auto configuration tool in Outlook is helpful (On Outlook Tray Icon, CTRL+Right click mouse and select “Test E-mail Auto Configuration”), it does not give detailed information on errors in the way the Remote Connectivity Tool gives. Below is an example of this test, with a successful result.


So, how do you use the tool? Go to the connectivity site and select the Client (beta) tab, depicted in the first image of this post.


It will verify Application requirements, if the tool isn’t installed yet a Security Warning appears:


You can click install if you want to install the tool. Now it will check for prerequisites. You will have to install prerequisite .Net Framework 4.5.


As I think this installation broke some .Net applications (MetroTwit) I would advise to install this on a testing computer and not on an Exchange server! That also makes it more easy to change host files and other things.

After installing .Net Framework 4.5 and rebooting your computer you can click the link on the Connectivity site again. If you are using Chrome or Firefox, you may need to install additional extensions. For Chrome (my main browser) you need to install ClickOnce for Chrome”. Firefox needs the Microsoft .Net Framework Assistant for Firefox.

After everything is set, the tool starts by using the links on the Connectivity site Client tab, ultimately the following screen popups:


For my issue, I used the “I can’t log on with Office Outlook” option and entered the account information as I would have on the site. Luckily no Captcha Winking smile.

After all the tests are run, you get the result screen. You can save it as an HTML file and/or review the results of the tests.


The HTML file is an awesome addition, as you can now easily send the results to a coworker for further examination. Below is an excerpt from such an HTML file. With the same formatting as the website and the tool. Note the red square, as you can see it has a non public IP address. Proving that this tool could be invaluable for local testing of Exchange connectivity.


Thanks to this tool I discovered that the AutoDiscover process failed at a later point than I first anticipated and that the certificate is loaded but failed to validate for the AutoDiscover domain name. As it turned out there is probably an issue with this specific certificate. Something that I previously probably only would have found out if I put this certificate into production and with a broken AutoDiscover process as a consequence.

Even if the tool is beta, it already helped me prevent unnecessary service disruption!

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