Is the laptop a domain member? If so it implicitly trusts all certs issued by 
your domain ca. In that case, create a ucc cert with all your needed cn's and 
that's it.

Make the request from a ps console and fulfil it through which ever means 
you're comfortable with against your ca. Easiest imho.

jlc

From: [email protected] [mailto:[email protected]] On 
Behalf Of Gavin Wilby
Sent: Wednesday, November 12, 2014 7:01 AM
To: '[email protected]'
Subject: RE: [Exchange] RE: Self sign certificate and Outlook Anywhere

Hi,

Thanks for the replies, this is all a bit new to me as in the past I have used 
SBS where all this is taken care of.

The domain already has a CA, the Exchange already has its own self sign certs.

Whats going to be the easiest way to achieve this? Can I not simply get outlook 
to ignore the certificate, or is this a massive no no?

Gavin Wilby
IT Support Engineer

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of ccollins9
Sent: 12 November 2014 13:25
To: exchange
Subject: Re: [Exchange] RE: Self sign certificate and Outlook Anywhere


Once you have it figured out where you will be getting the cert, be sure to 
issue a SAN cert with both the internal and external website names. SAN certs 
allow multiple DNS names on a single cert. The certificate request wizard in 
exchange will generate a cert request with multiple names by default. Also, if 
you are going to stand up your own CA, there is an additional step you must 
perform to allow it to issue SAN certs.

http://exchangeserverpro.com/how-to-issue-a-san-certificate-to-exchange-server-2010-from-a-private-certificate-authority/
Setup your own CA for your domain, the clients will trust it, then use the same 
ca to issue a cert for the right cn that your exch server will use.

Or use startcom to issue a free cert for the server.

jlc

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]<mailto:[email protected]>] 
On Behalf Of Gavin Wilby
Sent: Wednesday, November 12, 2014 5:29 AM
To: '[email protected]<mailto:[email protected]>'
Subject: [Exchange] Self sign certificate and Outlook Anywhere

Hi all,

I have Exchange 2010 that is running with a valid self signed certificate.

I need to set up a laptop with Outlook Anywhere, this seems to work fine right 
up until the point it tries to connect. It asks for credentials, and then 
immediately says:

There is a problem with the proxy servers security certificate. The name does 
not match...

This is because of course that out external name for the server, is not the 
same as the internal name.

Is there any work around for this to allow the client to connect?

Gavin Wilby
IT Support Engineer

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