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SBS2K8, GoDaddy SSL certificate updated and RWW not working

Posted on 2010-09-17
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Last Modified: 2012-05-10
Good afternoon Experts,

Another head scratcher for you.  The security certificate for our SBS 2008 expired this week, which dropped all the smartphone email syncs as well as put up certificate errors for Outlook each morning when the staff logged in.  We purchased a renewed one from GoDaddy (source of the original certificate).  I installed it, rebooted the server, next morning the users did not get their Outlook certificate errors, and thought the issue resolved.

Unfortunately, the phones still won't sync, and we've also discovered the Remote Web Workplace does not display either inside or outside the network.  I can ping, and it returns the correct static public IP address, and replies quickly, so I know it's up and pointed the correct way.  IIS is running, and we even tried restarting it (using IIS7).  At this point, we're a little stumped and not even sure where to begin troubleshooting.

Ideas?
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Question by:billyorr
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by:Rob Williams
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When you connect to the site and you check the certificate icon (the lock) does it show the correct certificate and expiry date?

Did you have a GoDaddy Certificate before? If not did you install the GoDaddy intermediate certificate as well?

Is the certificate present under IIS | Domain | IIS | Server certificates (withe correct expiry date)?

The smart phones usually have to be powered off and on before they will work with the new certificate, but RWW should be working.
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by:billyorr
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Thank you Rob!
Unfortunately we can't connect to the site at all, it simply returns "Internet Explorer cannot display the web page."  No lock at all, of course.
It was a GoDaddy cert vefore, and I installed the Intermediate certificate provided by them as well.
The certificate is present under IIS > click on the server name > click on Server Certificates, with correct dates.

That first observation is the weirdest, we have no idea how a certificate update could have brought down the whole site.  It would be easier if it was just an SSL or certificate error, but not seeing the site at all is very unusual.
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by:Rob Williams
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Sorry I missed that RWW wasn't working at all.

I would first check the service management console. Click on the "start up type" heading to sort by that category and see that all services marked automatic are showing as started.

If nothing seems obvious there try running the "fix my network wizard" located on the SBS console under Network | Connectivity

The SBS best practices analyzer will often locate startup and configuration issues as well:
http://www.microsoft.com/downloads/en/details.aspx?familyid=86a1aa32-9814-484e-bd43-3e42aec7f731&displaylang=en
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billyorr earned 0 total points
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Thank you for the link Rob, going to put that in my favorites as that will be handy in the future.

Resolved the issue here from information at http://blogs.technet.com/b/sbs/archive/2009/06/19/common-remote-web-workplace-rww-connect-to-a-computer-issues-in-sbs-2008.aspx.  Turns out when I exported and deleted the expired certificate, I needed to go back into the Terminal Services Gateway Manager and pick the current certificate.
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by:Rob Williams
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Good to know.
I assume then you did not use the wizard in the SBS console to request a certificate renewal? Doing so should do that for you automatically.
Glad to hear you have resolved. Thanks for updating.
--Rob
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