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I'm trying to understand how this is possible. This is my situation

Inside the company (LAN environment)

  • Outlook 2010,2013,2016 can connect successfully to exchange server. No problem here

Outside the company (Internet environment)

  • Outlook 2010,2013,2016 CANNOT connect to exchange server.
  • Mobile device using Outlook App, Gmail App, phone default mail app, etc CAN connect to exchange server. (when setting up email choose Exchange and type in the server address)
  • If I VPN to office, then Outlook 2010,2013,2016, can connect to exchange server

The Exchange server is 2010

Extra info on Outlook 2016. If you try to add new email account when outside the company. The autodiscover failed to retrieve the configuration. If you're inside the company, the autodiscover works fine.

I've tried to use autodiscover.xml file + adding entry to registry. The auto discover works (able to get configuration), but failed at last step (Logging on to the mail server) with this error message "The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."

My question are why mobile devices works without any problem? and how can I make Outlook works without modifying anything on server side.

Thank you, any help are greatly appreciated.

chmod
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    Is Outlook anywhere enabled? Have you ran the exchange remote connectivity analyzer? – JBaldridge Dec 02 '16 at 06:40
  • Can you post the output from the Autodiscovery Check from the [MS Remote Connection Analyzer](https://testconnectivity.microsoft.com/) in your question? You can change sensitive hostnames and domains to contoso or similar. – BastianW Dec 02 '16 at 08:46

2 Answers2

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Outlook and mobile devices (even software applications with Outlook in their name) connect in completely different ways. Therefore it is certainly possible for it to work for ActiveSync on mobile and to not work on Outlook in Windows.

"...how can I make Outlook works without modifying anything on server side."

Are you not the server admin? Outlook Anywhere needs to be specifically enabled on Exchange 2010 but there can be good reasons why it isn't enabled on your server. Trying to bypass restrictions placed on your network by the admins is not allowed on this site.

Sembee
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Mobile devices use ActiveSync which is located at https://youremailserver.com/activesync.

Your Outlook clients external to your organization would need to either use the VPN or Outlook Anywhere. If your Exchange system is broken up per role, the Outlook Anywhere and ActiveSync would reside on your CAS server.

You'll also have to make sure you've put in the correct DNS records with your public DNS registrar. There are a few ways to do this, most recommended would be a SRV record for _autodiscover

Jarrod L. J. Gibson
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