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Getting certificate error on my local network when connecting to exchange

Posted on 2014-10-08
Medium Priority
Last Modified: 2014-10-08
Exchange 2013

I can connect to a mailbox via outlook perfectly from outside the network, but within the local network I get this error below. It's not using the godaddy certificate or address. It's using the local server address as you can see.cert-error.jpg
Question by:cnl83
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Expert Comment

ID: 40368872
1. What version of Outlook are you using?
2. Does this happen to everyone?
3. Is this new / did it ever work?
4. Are you joined to the domain?
LVL 59

Expert Comment

by:Cliff Galiher
ID: 40368876
Is this not a question you already have open? As I said in your password question, the cause of the password prompt is because of a URL/SSL issue. The two are related and you are already working that problem. This only complicates issues and will add confusion.

Author Comment

ID: 40368941
That was isolated to just Outlook 2007. This is all clients now.
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LVL 35

Accepted Solution

Seth Simmons earned 2000 total points
ID: 40368967
you should not be using .local to connect internally; use your external (.com, .net or whatever it is) to connect internally
might need to configure split dns

Windows - Setting Up Split DNS
LVL 27

Expert Comment

ID: 40368975
LVL 59

Expert Comment

by:Cliff Galiher
ID: 40368976
Unfortunately the nature of EE (or any forum) is that experts are not sitting on your network and don't know the details of your implementation. As I stated in that thread, we reached a point where I believe you really need to call in a paid consultant to fix your issues. The reason I gave that advice at that time wasn't laziness, but was because there was a tipping point where a forum was no longer a good way to resolve your issue.

 I hate to say it, but by following some of the (blatantly bad) advice that was given to you after I dropped off that question, you've actually created this new error. They are not unrelated. The other drawback of a forum is that if you don't have some prerequisite knowledge, it is very difficult to filter "good" advice from "bad" advice. And since you aren't paying anyone, you have no warranty or recourse.

So I will again suggest that you should contact a local consultant in your area that you trust or find a reputable company that offers paid remote support and has a good reputation. I fear that if you continue to try to solve these problems through EE, you will only further create issues and may get yourself into a state you cannot get out of.

Ultimately, of course, that choice is yours.
LVL 19

Expert Comment

ID: 40368983
Please check in IIS default web site binded to proper SSL certificate. Go to EAC and click on server and go to certificate and check whether the correct certificate has IIS, SMTP, IMAP and POP3 services are assigned.
Verify certificate have SAN entries eg and Make sure DNS host A record is pointed to the exchange 2013 in internal DNS. If the DNS hots A record is not present then create a record.
run get-clientaccessserver | fl and check if autodiscoverurl is pointed to
Go to server and virtualdirectories and make sure all the virtual directories are configured with external and internal entries as

Expert Comment

ID: 40368985
I had to do this for a client, it sets exchange to use external name for internal. Change the name to your domain
Set-AutodiscoverVirtualDirectory -Identity * -internalurl “”
Set-ClientAccessServer -Identity * -AutodiscoverServiceInternalUri “”
Set-webservicesvirtualdirectory -Identity * -internalurl “”
Set-oabvirtualdirectory -Identity * -internalurl “”
Set-owavirtualdirectory -Identity * -internalurl “”
Set-ecpvirtualdirectory -Identity * -internalurl “”
Set-ActiveSyncVirtualDirectory -Identity * -InternalUrl ""

Open IIS Manager by clicking Start, then enter inetmgr.
Expand the server and expand Application Pools, then right-click on MSExchangeAutodiscoverAppPool, and select Recycle.

Author Comment

ID: 40369517

Going through each step in this link resolved my issue.

Author Comment

ID: 40369646
I've requested that this question be closed as follows:

Accepted answer: 0 points for cnl83's comment #a40369517

for the following reason:

It's what another Expert Exchanger provided to me to resolve my error. Though it did block my access to my own web site.
LVL 35

Expert Comment

by:Seth Simmons
ID: 40369647
I told you in the beginning not to be using .local and you may need to configure split dns.
Jason elaborated more on what I stated which both amounts to the solution.
you stated "It's what another Expert Exchanger provided to me to resolve my error." though selected your own comment as the solution.
LVL 31

Expert Comment

by:Gareth Gudger
ID: 40369853
Hey CNL83,

Just wanted to post here as well. Make sure you add an A record of "WWW" in your newly created split-brain DNS zone on your internal DNS server. Then point that to the public IP of your hosting provider for your website.

That will fix that issue.


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