How to connect to exchange 2010 from outlook 2010 when only an internet connection is present.

I have a user that is having difficulties connecting to his mail when he is not on the VPN. What use to happen was that he only needed an internet connection and he could log onto his email and retrieve everything. now when he is not on the VPN and does have a valid internet connection he tries to open his email and gets the login credential page  inputs his credentials and the email just hangs...

any ideas?
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MASEE Solution Guide - Technical Dept HeadCommented:
Open outlook using the below command and post the results
outlook.exe /rpdiag
cmdolcetAuthor Commented:
MAS, what is that suppose to do? When I write that in the command prompt it does nothing!
MASEE Solution Guide - Technical Dept HeadCommented:
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cmdolcetAuthor Commented:
OK everything looks good...however he gets prompted for a password and the credential box never goes away???

Also at the bottom of the status window just keep saving password credentials required.

and yes the password is correct!
There are times when the I have seen the username being incorrect.
Instead of domain\username outlook prompts with

Change it to domain creds, and make sure his auto-discover service is setup correctly.  It should be pointing to the external fqdn, not mailserver.domain.local

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cmdolcetAuthor Commented:
Ok how where I check the auto-discovery service is running and pointing to the external fqdn?
Jamie McKillopIT ManagerCommented:

Run the Exchange Remote Connectivity Analyzer to verify your settings are correct:

Mohammed HamadaSenior IT ConsultantCommented:
You need to check if the user's UPN (User Principal name) Matches his Email or not. You will need to check your Exchange's Outlook anywhere settings if it's configured properly and it has certificate assigned.

If exchange server is not configured with a public trusted certificate Outlook Anywhere or RPC over HTTP wont work properly unless the CA root certificate of the self signed certificate is imported in the Client's Trusted CA Root store.

You can check if you get proper result by following Jamie's link which is a microsoft connectivity tool that pass through the basic tests for Exchange connectivity.

Post any results that you get from there.
Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Hello cmdolcet,

1 Question does it work from another machine on internet ? - as if so no issues with anything but wither with Outlook maybe or some caching causing the issue

- Rancy
cmdolcetAuthor Commented:

Do I run this connectivity tool when I am connected to the Office Network or just when I am outside the network with Internet connectivity?
Jamie McKillopIT ManagerCommented:
It doesn't matter. The tests run from the remote server.

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