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We recently upgraded from W2K3/IIS6 to W2K8/IIS7 and have been having problems with our SSL Certificate (Thawte 123 SSL certificate) ceasing to work after rebooting.

Initially, the intermediate certificates would stop working and we could repair the problem by reinstalling all of them after the reboot (annoying, but not the end of the world). Unfortunately, this is no longer working. The certificate chain has been doublechecked by several tools and people with decent knowledge but no one has been able to identify the cause of the problem.

The bindings in IIS have been checked as well

The cert itself is also still valid.

NOTE 1: I have seen THIS question which seems to be very similar, but there is no satisfactory answer in that post and it's a year old so not likely to get one any time soon. NOTE 2: I'm asking this on behalf of a co-worker so won't be able to provide instant feedback to any questions/suggestions but I will pass it on.

The url is:

http://www.flirtalike.com / https://www.flirtalike.com

Screenshots:

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2 Answers

up vote 0 down vote accepted

We found a solution from HERE:

After the machine is rebooted, go to the IIS Manager and bring up the Bindings… window for the website in question. Then, select “https”, click on “Edit” then click “Ok” without making any changes to the settings. After doing this, browsing to https:// should now be successful.

We still need to do this after every reboot unfortunately, but at least we have working SSL!

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Gosh, that sucks. Have you opened a support ticket with Microsoft for that? This smells like a bug. Worth a hotfix. I would put it Prio A - a power failure - reboot - renders servers unusable, possibly at a BAD time. Cries for a hotfix. –  TomTom Jun 20 '12 at 7:46
    
Hehe, you're probably right @TomTom - however this happened over a year ago and we haven't been using that server for at least 6 months of that year. In other words, it's completely impossible for us to reproduce. Next time... –  Zac May 7 '13 at 20:40
    
Oh right, you asked that in 2012. I guess that happens when you review your profile once per year because you don't spend much time on Serverfault... –  Zac May 7 '13 at 20:46
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Install correct intermediate certificate into intermediate store according https://search.thawte.com/support/ssl-digital-certificates/index?page=content&id=SO15171&actp=search&viewlocale=en_US&searchid=1282614432001

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Thanks for the reply Pavel. Unfortunately, we won't be able to try this solution - my colleague tells me that we ended up getting an alternative certificate which no longer gives us any problems. –  Zac Jun 20 '12 at 10:13
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