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Avatar of adrecal
adrecal

Autodiscover works externally with Outlook 2016, but not works with Outlook 2013
I have a hybrid env with Exchange 2010 and Office 365.

When I create a mailbox on Exchange 2010 onpremises and create a new profile on Oultook 2013 (or Outlook 2016) inside my domain organization my autodiscover works fine.


When I create a mailbox on Exchange 2010 onpremises and create a new profile on Oultook 2013 outside my domain organization (across internet, without VPN) my autodiscover works fine on Outlook 2016, but not on Outlook 2013. My Outlook 2013 display the certificate popup, and I accept. And the message "server not could be found" appear. When I ping autodiscover.mydomain.com and mail.mydomain.com outside my organization the ping resolves OK.

What I miss??

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Avatar of J0rtITJ0rtIT🇻🇪

The address are well configured?
Internally and externally on the Exchange server Virtual Folders?

Check with this script run it from the exchange server powershell console:
https://gallery.technet.microsoft.com/office/Script-to-configure-the-5a58558b

With the option -get

What error do you get the certificate? (2 checks greens and 1 red?)

Avatar of adrecaladrecal

ASKER

Thanks for the rapid answer :)
The output:
User generated image
step by step:

Open Outlook 2013;
New Profile;
User generated imageThen this popup in loop:
User generated image
if I click Cancel:
User generated image
"An encrypted connection to your mail services is not available"

OR

New Profile;
User generated imageFirts Option

User generated image
After some seconds, Outlloks freeze and return:

 

"Connection to Microsoft Exchange is unavailable"

"The name could not be resolved. The connection to the Microsoft Exchange Server is unavailable. Outlook must be online or connected to complete this action."

OR:
New Profile:
User generated imageSecond option

User generated image
User generated image008.GIF

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Avatar of adrecaladrecal

ASKER

Mohammad Ishtyaq Khatri the mailbox is a Exchange 2010 mailbox, not a Office365 mailbox. The ADAL workaround not works

Avatar of J0rtITJ0rtIT🇻🇪

OK looks good for 2010 (since 2010 doesn't have the mapi folder that's why u get that error in the script).

Now, Please run this:

Get-ExchangeCertificate and post the result and make sure to mask the thumbprints.

Avatar of adrecaladrecal

ASKER

Jose Gabriel my certificate is a SAN certificate assigned to IMAP, POP, IIS, SMTP services.
My DNS names:

DNS Name=www.mydomain.com
DNS Name=mydomain.com
DNS Name=correio.mydomain.com >>> This is the servername used to configure my mail and my OWA internal/external address)
DNS Name=mail.mydomain.com
DNS Name=webmail.mydomain.com

Yes, I forgot autodiscover.mydomain.com.

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Avatar of adrecaladrecal

ASKER

Jose Gabriel look this:

if I configure the mailbox internally the autodiscover works, and I set the Outlook Anywere to:

https://correio.mydomain.com
msstd:correio.mydomain.com
Basic authentication

So I export the profile registry from regedit and import on the external computer.
The popup to login/pass appear. Cancel.

The profile works even the servername on profile configuration is my local server FQDN, not resolvable across internet.

This scenário is the most confuse i've ever seen :P

Avatar of J0rtITJ0rtIT🇻🇪

I don't need to see ur certificates, what I need to see are the "services" assigned to all the certificates so I can figure out what is the certificate you are using in the IIS. and I can determine what to do next.

Looking at that you only need to rekey that certificate to include just:
correio.<yourdomain>.com
autodiscover.<yourdomain>.com

That's it .

Avatar of adrecaladrecal

ASKER

Good afternoon, gentlemen, I've been away for health reasons.
Today I realized that my account can be configured via autodiscover correctly when the client is Outlook 2016. However an authentication popup repeatedly appears requesting the credentials of the configured account. How to solve this question definitively? I have already cleared the credentials in the Windows credential manager and the popup keeps popping up. The clients is outside my domain. The UPN is the same value from my smtp address on ProxyAddresses ActiveDirectory attribute.

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Avatar of J0rtITJ0rtIT🇻🇪

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Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.