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Recently, all my Outlook users get this certificate error message twice when they launch Outlook (doesn't matter what Outlook version it happens on all of them) and connect to the exchange server.

It comes up twice, they click Yes twice and it doesn't come back until the next time they open/close outlook. If you View the certificate and install the certificate, the error still comes back.

There is a complex Microsoft KB article showing about 6 settings that need to be modified in the command-line interface of Exchange 2007. I just don't think this is proper for the problem.

Has anyone else had this come up on Small Business Server 2008 / Exchange 2007 and have a fix?

See picture attached.

thanks in advance-
OutlookError.jpg
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  • errormessage
OutlookError.jpg
OutlookError.jpg
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  • errormessage
OutlookError.jpg
OutlookError.jpg
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  • errormessage
OutlookError.jpg

    asked 12/07/2011 10:11

    dassowrwd's gravatar image

    dassowrwd ♦♦


    9 Answers:
    Check the date of the SSL Cert as judging by your pics it has expired which explains the error messages.
    Is this a self-signed cert?
    link

    answered

    Spartan_1337's gravatar image

    Spartan_1337

    Yeah I'm sure it was just auto-generated when I installed SBS 2008. Can I just re-create it in IIS or Exchange Console somewhere? We don't own any external SSL certs...
    link

    answered 2011-12-07 at 18:15:06

    dassowrwd's gravatar image

    dassowrwd

    Open up your exchange managment console and renew your certificate.  The cert is most likely self-signed.

    http://blog.kazmarek.com/2010/11/17/renew-ssl-self-signed-certificate-in-sbs-2008/
    link

    answered 2011-12-07 at 18:34:56

    uescomp's gravatar image

    uescomp

    Since I didn't use any of the SBS wizards to set up the server or exchange I couldn't use uescomp's solution.

    I was able to solve it by launching the Exchange 2007 Management Shell and simply typing the command:

    New-ExchangeCertificate

    with no parameters.... then type Y when prompted to overwrite the old certificate. Problem fixed.

    Thanks all for pointers.....
    link

    answered 2011-12-07 at 18:51:20

    dassowrwd's gravatar image

    dassowrwd

    I've requested that this question be closed as follows:

    Accepted answer: 500 points for uescomp's comment http:/Q_27483558.html#37253674
    Assisted answer: 0 points for dassowrwd's comment http:/Q_27483558.html#37253756

    for the following reason:

    If you used SBS wizards, follow uescomp's solution.<br /><br />If you DID NOT use SBS wizards, follow my solution.

    link

    answered 2011-12-07 at 19:30:43

    dassowrwd's gravatar image

    dassowrwd

    I thought this was fixed by just running new-exchangecertificate. This did NOT fix it as I thought it had.

    Anyone have any ideas? It's clearly the certificate on the client side of exchange/outlook. Again I can't use the SBS wizards they don't work for the most part since the server wasn't setup using them.
    link

    answered 2011-12-07 at 19:32:13

    dassowrwd's gravatar image

    dassowrwd

    I have found the expired certificate. It is in IIS 6.0 Manager under Server Certificates.

    When I try to right click and renew the expired certificate for "sites" it won't accept anything I type in the "Specify Online Certificate Authority" box. Since I want to self sign the renewal, what would be acceptable to put in this box?

    I think this may be the key...... literally.
    link

    answered 2011-12-08 at 09:23:01

    dassowrwd's gravatar image

    dassowrwd

    I have simply deleted the expired certificate "Sites" and the error has gone. All outlook functionality seems to be working just fine without the certificate....... Could this be the solution?
    link

    answered 2011-12-08 at 10:02:40

    dassowrwd's gravatar image

    dassowrwd

    It is safe to delete the "Sites" certificate automatically created by the migration from Small Business Server 2003 to Small Businss Server 2008 and expires causing outlook errors after 2 years of being live on SBS 2008.

    link

    answered 2011-12-10 at 16:48:46

    dassowrwd's gravatar image

    dassowrwd

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    Asked: 12/07/2011 10:11

    Seen: 225 times

    Last updated: 12/15/2011 05:17