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Our organization just moved our Website/Domain to a hosted VPS. We elected, for the time being, to keep our email (Exchange) running at our office.

On our new VPS, we simply add a DNS record to redirect our mail to our on-site exchange server. This worked out well, as mail is coming and going with no problems.

Recently, we ran across an issue when setting up outlook from outside of our office (Not on same network as exchange server). When configuring mail server address, it keeps prompting for credentials.

Anyone got any ideas on why this is happening? Is our VPS not allowing Outlook to find our exchange server? If so, how can we bypass it?

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How do you have Outlook configured: POP, IMAP, MAPI, or RPC over HTTPS? – joeqwerty Feb 15 '10 at 20:36
Do you have anything between your Exchange server and the Internet that may be wanting authentication, such as ISA? – John Gardeniers Feb 15 '10 at 20:42

Make sure you have helper ip addresses setup in your pix. If you are using vpn connectivty or any other authentication type, your helper addresses should help pointing the outlook client to the internal dns servers.

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PIX? He didn't mention anything about a pix device. – DanBig Aug 5 '10 at 19:50

If you are using RPC over HTTPS, you will always have to authenticate, there is no way around this. The PCs that are getting Outlook setup, are they domain computers that belong to the same domain as Exchange?

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The usual fix would be to require Outlook users outside your LAN to connect to your network using a VPN client. Your edge firewall may already provide the functionality that you need.

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