Windows Server Essentials – Configuration Troubleshooter
February 14, 2014 105 Comments
I had a support case this week where it became apparent to me that there is no quick and easy way to test Essentials Servers for Configuration errors. Manually working through IIS or Certificates is prone to human error, as was proved to me, by me missing certain key things.
Uncharacteristically i decided to write a PowerShell script to save me from this sort of embarrassment in the future, and make me look really good next time i need to troubleshoot an Essentials Server.
You can download the tool from here, and am very interested to hear how it works for you.
If you have already downloaded it, i have updated the tool so you should download it again!
What does the tool do?
Well, it checks a number of things that i have found are the key things that make an Essentials Server tick. That is IIS and MOST IMPORTANTLY, Certificate Services.
I knew that the CA was pretty significant to an Essentials Server, but i didn’t know just how deep that significance went. In your Local Machine Certificate Store you have a number of Certificates, perhaps the most important file on the whole server (aside from perhaps ntds.dit) is your Certificate Authority Root Certificate. Without that, you cannot correctly reinstall the CA, and without that CA, you can’t do anything. It is not just a case that you cant reinstall the CA, you can. The CA requires a specific name, and if you reinstall and generate a new key, the name is not likely to remain correct.
There may well be a way to get around even that scenario by hacking the crap out of AD, but honestly, i think i might take a reinstall over that.
That was a bit of a side track, so, again, what does this tool do?
Firstly it will decide if you are running on Essentials 2011, 2012 or 2012 R2.
It will then give you the choice of testing IIS or your CA. If you choose to test your IIS Configuration, it will inspect your Web Site Configuration, your Application Pools, Virtual Directories and ISAPI filters as well as your Web Site Bindings.
When you check the CA, it will check that the CA is available, that it has the right name (that is important), that the certificate set in the Registry for the Dashboard matches what you have in your Local Machine Store, it will even download a copy of the CRL from your server and test that it is publishing the right information.
It compares all of this information to ‘’Defaults’ and lets you know where you may have problems.
I have run it against SBS 2011 Essentials, Essentials 2012, and R2, and it has identified the deliberate errors i have introduced and reported back correctly once those have been repaired.
i haven’t made it to be an exhaustive tool of everything that could possibly go wrong on an Essentials Server, it really is just focussed on IIS and the CA, even then it may not cover every scenario. Hopefully if you do come across a broken Essentials Server using this will do enough to point you to the fix, or at least help to rule some things out.