Good Morning,

I am a Network Administrator for a small non-profit organization that has been running technology -- a mail server for example -- that needed to be put to farm long ago.  Old mail server running 2003 with Exchange 2007, if that's any indication.  Anyways, I've been building a new mail server and have just about everything in place, including an MX record.  Unfortunately, Outlook Anywhere doesn't seem to work on workstations once they're off-site.  Right now, I only have three test accounts set up on the new mail server, so business operations hasn't been impacted... yet.

Here's what I've done so far:

1. Installed mail certificate from issuer, enabled IMAP, POP, UM, IIS, SMTP services.

2. Under Server Configuration > Client Access > Outlook Anywhere, I've enabled Outlook Anywhere with the external host name set to mail.ourorganization.org.  NTLM based authentication.

3. Went into our UTM and added all the necessary NAT and Firewall rules (I'm pretty sure of this, but I have a call with our vendor to verify later today)

Going to https://testconnectivity.microsoft.com, I ran the Outlook Connectivity Test and ran into this.  Everything came through with the exception of the three records below.  Please note that I've altered the domain and ip address information for security purposes.  Any suggestions?  Please let me know if there's any additional information you require.

• Edited by Coolhead2015 19 hours 7 minutes ago

Hi,

this might be that Outodiscover directory has not been configured.

Can you browse https://autodiscover.domain.com/autodiscover/autodiscover.xml ?

You should be prompt with entering username and password.

In ECP, please go to servers - open your server and click Outlook anywhere.

edit internal and external hostname to mail.domain.com.

This name should be in your cert.

Is your cert 3rd part?

Good Morning,

I am a Network Administrator for a small non-profit organization that has been running technology -- a mail server for example -- that needed to be put to farm long ago.  Old mail server running 2003 with Exchange 2007, if that's any indication.  Anyways, I've been building a new mail server and have just about everything in place, including an MX record.  Unfortunately, Outlook Anywhere doesn't seem to work on workstations once they're off-site.  Right now, I only have three test accounts set up on the new mail server, so business operations hasn't been impacted... yet.

Here's what I've done so far:

1. Installed mail certificate from issuer, enabled IMAP, POP, UM, IIS, SMTP services.

2. Under Server Configuration > Client Access > Outlook Anywhere, I've enabled Outlook Anywhere with the external host name set to mail.ourorganization.org.  NTLM based authentication.

3. Went into our UTM and added all the necessary NAT and Firewall rules (I'm pretty sure of this, but I have a call with our vendor to verify later today)

Going to https://testconnectivity.microsoft.com, I ran the Outlook Connectivity Test and ran into this.  Everything came through with the exception of the three records below.  Please note that I've altered the domain and ip address information for security purposes.  Any suggestions?  Please let me know if there's any additional information you require.

Does OWA work correctly externally? What about ActiveSync? If that works then that should indicate the NAT and firewall access rules are good.

Also can you run Get-OutlookAnwhere -Server <Exchange2013> | fl server, *host*, *auth*, *ssl*

Hello,

Yes, I did browse out to that path and was greeted with a username and password prompt.  Also made sure that ECP was configured, but our internal domain and external domain are named differently.  The cert includes autodiscover.

Everything seems to work properly except for Outlook Anywhere for the Outlook client.  I'm able to access OWA from outside the network, and adding one of the mail test accounts to a mobile device also allows me to send and receive email from the outside. 

• Edited by Coolhead2015 17 hours 52 minutes ago

During profile creation in Outlook, at which step does it stop?

What error do you get when it fails?

Please run this command in Exchange powershell:

Get-mapivirtualdirectory

Check internal url what it is set to.

If internal url is set to use computer name,then change it to mail.domain.com instead.

The Outlook profile was built while the PC was inside the network. I tried running get-mapivirtualdirectory (this is a E2010 box), but it comes back with

Running get-outlookanywhere came up with this.  Might be the source of the problem?  Not sure how to proceed though.

Quick update.  I realized RPC over HTTP feature wasn't installed.  Installed it.  Connection status for exchange shows an established status on RPC/HTTP.  It's always the easy things.  Thanks guys!