Solved

New 3rd Party SSL Certificate Stops OWA and Activesync working

Posted on 2013-01-07
13
759 Views
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
0
Comment
Question by:jerseysam
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 6
  • 6
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 250 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.
0
Are your AD admin tools letting you down?

Managing Active Directory can get complicated.  Often, the native tools for managing AD are just not up to the task.  The largest Active Directory installations in the world have relied on one tool to manage their day-to-day administration tasks: Hyena. Start your trial today.

 
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 250 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

Featured Post

Has Powershell sent you back into the Stone Age?

If managing Active Directory using Windows Powershell® is making you feel like you stepped back in time, you are not alone.  For nearly 20 years, AD admins around the world have used one tool for day-to-day AD management: Hyena. Discover why.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

In-place Upgrading Dirsync to Azure AD Connect
A couple of months ago we ran into an issue that necessitated re-creating our Edge Subscriptions. However, when we attempted to execute the command: New-EdgeSubscription -filename C:\NewEdgeSub_01.xml we received an error indicating that the LDAP se…
In this video we show how to create a Shared Mailbox in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Recipients >> Sha…
To show how to generate a certificate request in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.:  First we need to log into the Exchange Admin Center. Navigate to the Servers >> Certificates…
Suggested Courses

636 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question