Friday, June 29, 2012

Troubleshooting SSL Issues in IIS

If you are like me, you frequently use Self-Signed certificates.  Unfortunately, one of the problems with using Self-Signed certificates is that they frequently cause browser issues (especially with Internet Explorer).  Whereas other browsers such as Mozilla Firefox and Google Chrome will actually provide detailed information about the errors discovered with the SSL Certificate, Internet Explorer in many cases will simply refuse to connect altogether (yet another reason to NOT use Internet Explorer).

Even though SSL certificates will probably continue to be the bane for Internet Explorer users for the foreseeable future, fortunately, there is a tool available to help you further troubleshoot these issues.

If you ever had to deal with troubleshooting SSL Certificates in the days of IIS 6, you probably remember the good old SSL Diagnostics tool published by Microsoft: http://www.microsoft.com/en-us/download/details.aspx?id=674

Unfortunately, Microsoft does not seem to have published and released a new version of SSL Diagnostics for IIS 7 and above.  But do not lose all hope just yet....  A clever Microsoft developer has released a version of the SSL Diagnostics tool for IIS 7 and above that can be downloaded from here: http://blogs.msdn.com/b/vijaysk/archive/2009/09/20/ssl-diagnostics-tool-for-iis-7.aspx

It functions in a similar manner as the old SSL Diagnostics tool by enumerating all of the IIS websites and providing details specific to the SSL Certificate configurations on each of them:


So if you are experiencing unknown issues presumably due to bad SSL certificates, you now have a tool that can help you troubleshoot those nasty SSL browser problems!

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