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New 3rd Party SSL Certificate Stops OWA and Activesync working

Posted on 2013-01-07
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Last Modified: 2013-02-08
Hi,

I have recently been asked to change the exisiting self-signed SSL Certificate on a server for a 3rd party Certificate for compliance reasons.

I have new certificates from www.networksolutions.com.

The exisiting certificate is for "mail.mydomain.com" issued by "mail.mydomain.com"

My new one if for "mail.mydomain.com" issued by Network Solutions DV Server.

I have installed the 2 other certificates (AddTrustExternalCARoot) and (NetworkSolutionsDVserverCA) to the Intermediate Certification Authorities Certificates using MMC and Certificates. As well as placing the "mail.mydomain.com" certificate into Personal.

However, as soon as i replace my existing self-signed certificate (which all works) with the new NetworkSolutions Certificate, OWA and Activesync stop working.

What am I missing? Help
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Question by:jerseysam
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13 Comments
 
LVL 18

Expert Comment

by:irweazelwallis
ID: 38750824
what SAN's have you included in the certificate

what services have you attached to the certificate

once you have changed it over you can use https://www.testexchangeconnectivity.com/
to check for errors
0
 
LVL 15

Author Comment

by:jerseysam
ID: 38750840
I only included our "mail.mydomain.com"

how do i attach services etc?

Shall i post the https://www.testexchangeconnectivity.com/  log?
0
 
LVL 17

Accepted Solution

by:
OriNetworks earned 500 total points
ID: 38750946
Was the self-signed cert also for mail.mydomain.com or simply mailservername? You may need to install any trusted roots that are not currently on your clients.
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LVL 15

Author Comment

by:jerseysam
ID: 38750966
Yes self-signed was exactly same (mail.mydomain.com).

How do i install trusted roots on clients and iphones etc?
0
 
LVL 18

Expert Comment

by:irweazelwallis
ID: 38750973
it depends on how you have your external service configured

is OWA and Active Sync pointed at the same url i.e. https://mail.mydomain.com/owa or
https://mail.mydomain.com/active-sync
0
 
LVL 18

Expert Comment

by:irweazelwallis
ID: 38751007
to attach services...

http://www.digicert.com/ssl-certificate-installation-microsoft-exchange-2010.htm

follow the last bit - if you assign IIS then that will cover OWA and Active Sync

if you post the log then it might be easier to see where any possible problems are
0
 
LVL 15

Author Comment

by:jerseysam
ID: 38751016
Exchange 2003 and IIS v 6.0 so dont seem to have assign services
0
 
LVL 18

Expert Comment

by:irweazelwallis
ID: 38751031
ahh sorry, my fault had assumed 2007 or 2010


you will probably need to do something in IIS, let me have a check its been a while since i played with 2003
0
 
LVL 18

Expert Comment

by:irweazelwallis
ID: 38751056
0
 
LVL 15

Author Comment

by:jerseysam
ID: 38751068
Yep.

think i need to create a new CRS request or somehting?

Seems that OWA works internally on server. Iphones do not work. OWA not working externally
0
 
LVL 15

Author Comment

by:jerseysam
ID: 38854401
I think the issue is that when i created my CRS then i may not have chosen the correct info.

In exchange my DNS says "mydomain.com" but my FQDN is "servername.mydomain.local"

What info should i use in my CRS? The self-generated certificate that works with iphones is "servername.mydomain.local"

Help
0
 
LVL 18

Assisted Solution

by:irweazelwallis
irweazelwallis earned 500 total points
ID: 38854532
for your certificate it should contain

external server fqdn i.e. owa.yourexteranldomain.com

as you are attaching this to your IIS service on exchange for owa you either need to include at least the following as well

internalserver.mydomain.local
netbios name
autodiscover
0
 
LVL 15

Author Comment

by:jerseysam
ID: 38854547
Yes i thought internalserver.mydomain.local is what i need, as this works correctly if i use a self-signed and generated SSL certificate.

Will need to create a new CRS and ask the 3rd party to issue a new certificate (is they will for a .local).
0

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