Hi everyone,

I have the following issue in our Demo environment.

Outlook cannot connect when adding a profile in outlook, even though the Outlook Connectivity Check can reach the environment.
Even though the certificate does not match. Our OWA, Android en iOS connections are working (iOS is giving a cert error)

I tried outlook anywhere but sadly enough, this did not work either.

I have 2DC's and 2EXCH server which are set-up with domain.nl

I have also added a UPN Suffix so we can use domain2.nl in our enviroment.

Please help me out to solve this.

Kind regards
Justin

• Edited by JustinoFTW Monday, June 22, 2015 1:56 PM

Unfortunately Outlook will not connect if the certificate isn't correct. In the past, you would get a cert error and could click "Continue" to get connected but that's no longer the case. You can always use one of the exchange self generated certificates. You would just need to export it from your exchange server and import it on to your test clients.

Is this new since Exchange 2013?

I'm not at the office anymore, but it said something like " Could not logon. Check the connection.........." when i'm adding a profile with an account for this new environment. 

• Edited by JustinoFTW Monday, June 22, 2015 4:11 PM

This is my connectivity test from Microsoft.

https://www.dropbox.com/s/6ez8dj71s4uhxcc/rcatest.html?dl=0

• Edited by JustinoFTW 22 hours 56 minutes ago

MAPI over HTTP which is the new protocol in 2013 is DISABLED by default. Unless you enable the protocol which is org wide and can't be tailored down unfortunately, you can rule that out.

Few questions:

1. Can you connect using any version of Outlook at all?

2. If you are trying internal connectivity, you dont need all the autodiscover.domain.com urls (irrespective of how many email domains you have). All you need to configure is the SCP, which can be a url IN THE CERT and routable to CAS (direct or via a load balancer).

MAPI over HTTP is not enabled, atleast i have never Enabled it and i'm the only one working on this environment.

1. No, tested with Outlook 2010 and Outlook 2013

2. We don't have internal mail. Since this environment is only used from the outside (outlook anywhere etc.)
I have tested this from another Internal IP range outside the domain, and after adding email.domain1.nl in the outlook anywhere field it asks for my password and after that accepts my information and adds the profile. Externally sadly enough, nothing happens after pressing "Check names"

EDIT: I just entered email.domain1.nl in the outlook anywhere field on an External Clietn, and it asks for my credentials. After this it gives me the following: 
"Outlook can not log on. Verify you are connected to the network and are using the proper server and mailbox name. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action." 

Can it be an issue when my internal domain (domain1.nl) is the same as the external domain (domain1.nl)?

• Edited by JustinoFTW 22 hours 11 minutes ago

How are you publishing Outlook Anywhere externally? Straight NAT or through a reverse proxy?

And you dont have any autodiscover urls for domain2.nl in the cert and hence it will fail. I persume that everything works with domain1.nl user?

Outlook anywhere is going rought autodiscover.domain*.nl directly to our mail environment

I dont have any autodisover.domain2.nl in my certificate. Only a *.domain.nl wildcard certificate.
Sadly enough i can not test domain1.nl since the autodiscover record is currently pointing to our current environment instead of the new test envorinment

This is my connectivity test from Microsoft.

https://www.dropbox.com/s/6ez8dj71s4uhxcc/rcatest.html?dl=0

• Edited by JustinoFTW Tuesday, June 23, 2015 8:30 AM

You can set host file entries on your workstation to map your DNS names to the new test environment.

What you posted from the exchange connectivity test shows that your URL's seem to be setup correctly.  I'm afraid that until your get your SSL cert correct that you aren't going to be able to connect.

For testing, you can generate exchange signed certs.  You will just need to export them and install on your workstation in order to not receive certificate errors.

MAPI over HTTP is not enabled, atleast i have never Enabled it and i'm the only one working on this environment.

1. No, tested with Outlook 2010 and Outlook 2013

2. We don't have internal mail. Since this environment is only used from the outside (outlook anywhere etc.)
I have tested this from another Internal IP range outside the domain, and after adding email.domain1.nl in the outlook anywhere field it asks for my password and after that accepts my information and adds the profile. Externally sadly enough, nothing happens after pressing "Check names"

EDIT: I just entered email.domain1.nl in the outlook anywhere field on an External Clietn, and it asks for my credentials. After this it gives me the following: 
"Outlook can not log on. Verify you are connected to the network and are using the proper server and mailbox name. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action." 

Can it be an issue when my internal domain (domain1.nl) is the same as the external domain (domain1.nl)?

• Edited by JustinoFTW Tuesday, June 23, 2015 9:15 AM

Does that explain why my outlook gives me this?

"Outlook can not log on. Verify you are connected to the network and are using the proper server and mailbox name. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action." 

I will give it a try tommorow

You can set host file entries on your workstation to map your DNS names to the new test environment.

What you posted from the exchange connectivity test shows that your URL's seem to be setup correctly.  I'm afraid that until your get your SSL cert correct that you aren't going to be able to connect.

For testing, you can generate exchange signed certs.  You will just need to export them and install on your workstation in order to not receive certificate errors.

Does that explain why my outlook gives me this?

"Outlook can not log on. Verify you are connected to the network and are using the proper server and mailbox name. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action." 

I will give it a try today/tommorow

Hmm, i have tried everyone i could think of.

I will start over and give it another try with an other domain.
Thanks for the help everyone!

During the Outlook Account setup, do you receive a certificate warning?

I'm able to reproduce the exact same behavior you are describing.  We use a certificate signed by our internal enterprise CA for our internal Exchange URL's.  This requires the enterprise CA root certificate installed on the clients workstations.  On my test workstation, if I remove the root CA, I start getting certificate errors when attempting to open an existing outlook profile and it will not connect.  If I create a new profile, I can get past the point of where Outlook Establishes the network connection and searches for my account settings.  After that I get a login box along with a certificate error, then I get "Connection to Microsoft Exchange is unavailable".

If I add the root CA cert back, I no longer get certificate errors and Outlook 2013 works fine.  If you can get your certificates working correctly, it should work fine.

During the Outlook Account setup, do you receive a certificate warning?

I'm able to reproduce the exact same behavior you are describing.  We use a certificate signed by our internal enterprise CA for our internal Exchange URL's.  This requires the enterprise CA root certificate installed on the clients workstations.  On my test workstation, if I remove the root CA, I start getting certificate errors when attempting to open an existing outlook profile and it will not connect.  If I create a new profile, I can get past the point of where Outlook Establishes the network connection and searches for my account settings.  After that I get a login box along with a certificate error, then I get "Connection to Microsoft Exchange is unavailable".

If I add the root CA cert back, I no longer get certificate errors and Outlook 2013 works fine.  If you can get your certificates working correctly, it should work fine.

• Proposed as answer by Winnie LiangMicrosoft contingent staff, Moderator Tuesday, June 30, 2015 2:10 AM
• Unproposed as answer by JustinoFTW 23 hours 43 minutes ago

During account setup is does not even give me an option for credentials. It can not connect i guess even though it is available. 

I have tried the Certificate trick, but sadly enough that did not help either.