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Exchange 2010 SSL Certificate errors

Good day ya all,

I have a question about Exchange 2010 SP1.  When I try to connect a client on RPC/HTTPS I keep getting a certificate error.  I have a self signed certificate from our own internal CA.

I can connect Phones and Tablets 100% working, but as soon as I try to connect any outlook client to run on RPC a get a error stating that the certificate is not trusted.

Now I now from looking around on the net that all white papers say that I have to install a third Party Trusted SSL certificate, but a SAN certificate is not cheap any more from my currency to Dollar, an my Director does not want to pay the money.

So my question is, is there any way to tell outlook or exchange to disgard certificate error and just connect to exchange anyway no matter what.  I dont care if its a secure connection on not, I just want outlook to connect.

I have setup my DNS Records, OWA is working from the outside.
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1 Solution
Simon Butler (Sembee)ConsultantCommented:
First - Exchange 2010 SP1 is very old and no longer supported. You should upgrade to Exchange 2010 SP2 or SP3.

Internal CA's are a pain to get working correctly. A SAN certificate is $60/year - if you use a GoDaddy reseller then you can usually purchase in your own currency. It will make life a lot easier and you will not have to tell users to ignore errors in OWA.

If you browse to OWA from the client do you get an SSL prompt? If so then that is your problem. Outlook Anywhere doesn't cope well with the prompts.
You need to import the root certificate of your internal CA to the client.

As for ignoring the errors - no, that isn't possible. That is why using a trusted certificate is a must.

Sick_PuppyAuthor Commented:
Hi Simon,
You are spot on,When browsing to OWA,I do get the SSL warbing page.  But my proplem is that Outlook does not connect at all,even if you accept the certificate error it then just gives a certificate name mismatch error and then disconnects.

The certificate that tou are talking about,is that the certificate on exchange or the one from the DC that I should import into the client machine?

Simon Butler (Sembee)ConsultantCommented:
Outlook cannot cope with the certificate prompt, so that will stop Outlook Anywhere from connecting.

I am referring to the root certifcate on the Certificate Authority. I don't deploy CA for any clients (I always use commercial certificates) so I am not sure where you download it.

You don't want to download the server's own certificate.

Seth SimmonsSr. Systems AdministratorCommented:
This question has been classified as abandoned and is closed as part of the Cleanup Program. See the recommendation for more details.
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