Outlook 2010 SSL in Windows 8 not connecting

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Re: Outlook 2010 SSL in Windows 8 not connecting

Postby virgild » Thu Dec 13th, 2012 3:07pm

When I test the connection in Outlook I get a message stating that "A secure connection to the server could not be established." It is the same error message as before.
I've been looking at our certificate. It's a Rapid SSL issued certificate that requires an intermediate certificate. The intermediate certificate is installed in Intermediate Certification Authorities on our server. However, when I do an SSL check on port 443 using a site like Geocerts SSL Checker it fails to find a valid root CA certificate. I am wondering if this has bearing on the issue. How does Mailtraq handle certificates that require an intermediate certificate?
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Re: Outlook 2010 SSL in Windows 8 not connecting

Postby Elric Pedder » Thu Dec 13th, 2012 3:35pm

virgild wrote:When I test the connection in Outlook I get a message stating that "A secure connection to the server could not be established."

Is that message for POP3S or SMTPS? I ask because it does make a difference. Outlook appears to use different security protocols and in one of my tests after the patch POP3S worked fine but SMTPS resulted in an error similar to this caused by the certificate.

virgild wrote:I've been looking at our certificate. It's a Rapid SSL issued certificate that requires an intermediate certificate. The intermediate certificate is installed in Intermediate Certification Authorities on our server. However, when I do an SSL check on port 443 using a site like Geocerts SSL Checker it fails to find a valid root CA certificate. I am wondering this has bearing on the issue. How does Mailtraq handle certificates that require an intermediate certificate?

Mailtraq send the entire certificate chain if it has it in the certificate file. Typically when you import a certificate you don't get the entire chain though. Chained certificates like this are really more for use in intranets where you can distribute the CA. If you are looking for a cheap certificate that does not require a private intermediate I can always help you with that.
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Re: Outlook 2010 SSL in Windows 8 not connecting

Postby virgild » Thu Dec 13th, 2012 4:31pm

Can I import a concatenated certificate, containing the intermediate certificate, into Mailtraq? If it doesn't work, can I revert back to the original certificate?
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Re: Outlook 2010 SSL in Windows 8 not connecting

Postby Elric Pedder » Sun Jan 06th, 2013 10:55am

virgild wrote:Can I import a concatenated certificate, containing the intermediate certificate, into Mailtraq? If it doesn't work, can I revert back to the original certificate?

I'm very sorry for the delay. The answer became quite complicated and I haven't resolved it yet. In principal you can certainly try and revert without problems but Mailtraq will only issue the relevant certificate and I'm working on finding out how we can reliably issue the chain when necessary.
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Re: Outlook 2010 SSL in Windows 8 not connecting

Postby virgild » Mon Feb 11th, 2013 6:15pm

Just wanted to report back that Outlook SSL is working after disabling both TLS 1.2 and SSL 2.0 via the Win 8 registry.
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Re: Outlook 2010 SSL in Windows 8 not connecting

Postby mollcons » Mon Mar 10th, 2014 5:10pm

Elric

I have just hit this issue with a migration from Outlook 2013 on Windows 7 Pro x64 to Outlook 2013 on Windows 8.1 x64. Using exactly the same configuration on both PC's, the Windows 7 PC works seamlessly, while the Windows 8.1 fails to connect with the same error as reported above. I don't really want to disable the clearly updated TLS/SSL versions in the registry unless I absolutely have to. Have you got anywhere with updating Mailtraq to cope with this?
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