Sunday, 27 May 2018 | tralala:)

Outlook 2010 prompts for smart card authentication, SSL certificate


Today some users reported that Outlook 2010 prompts them for smart card authentication. More and more users were affected by the time.

While no changes have been made on the Exchange server 2010 side, SSL certificate has been installed on our main webserver, where our website is running. Since we share the same DNS for WWW and EMAIL services the issues must have been connected somehow.

Everyone can found an MS article suggesting changing SSL configuration on the Exchange server, however in our case this has already been done.  

So I tried “Test Email Autoconfiguration” ( ) in Outlook 2010 and it stuck. Looking at the log revealed some problems connecting to which is one of the first URL’s to try in autodiscover sequence.

Well, but domain is our WWW server where I just installed SSL! And from now on, it was easy - just jump on the server open the website in IIS and while in SSL setting Under Client certificates, select Ignore. This way, autodiscover works properly in Outlook 2010 (it skips the URL as there is no autodiscover.xml) and does not prompt users for smartcards anymore.

1 comment

  1. I had the same problem, and wokerd with it for a couple of hours. What I noticed was it works just fine with a plain text' style password no special characters, numbers or capitol letters. After I changed the password to a plain text style, it wokerd perfectly.just my $.02

    — Sasha Sat, 20 Apr 2013

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