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Is there a simple and secure way to make Outlook 200x work with Exchange Server 2003 (SBS) whether I'm inside or outside the LAN?

I've tried the VPN method, but it doesn't always work since it's sometimes blocked on foreign LANs.

Edit1: Seems everyone is pointing to RPC over HTTPS. I will give it a try, post the results. Thanks.

Edit2: Seems I got it working, but I'm having problems connecting when on the LAN, it works fine when outside the LAN. I get errors about the certificate.

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Hi Atlas; can you edit your post with details/screenshots on the err messages that you're receiving? – p.campbell Jul 9 '09 at 16:40

Have you considered Outlook Anywhere?

For remote connections, Outlook offers Outlook Anywhere, an alternative to VPN connections that allows you to use Outlook just as you normally do at your organization, without the need for any special connections or hardware, such as smart cards and security tokens. Outlook can connect to Exchange through the Internet by using remote procedure call (RPC) over HTTP. The Outlook Anywhere feature allows you to access your Exchange account remotely from the Internet when you are working outside your organization's firewall.

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Do you know how I can solve the certificate problem? – Atlas Jul 9 '09 at 14:04

See for my walkthrough of setting up Outlook Anywhere. Unless you use SBS (in which case the wizard does it) getting Outlook Anywhere working can be a bugger, but my walkthrough is tried and tested by many happy sysadmins :-)

NB Outlook Anywhere only works with Outlook 2003 and 2007, so if the 200x in your post includes Outlook 2000 and Outlook XP you're stuck with Outlook Web Access.


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RPC/HTTPS aka Outlook Anywhere is what you're looking after, If you don't have a PKI in place you can use openssl to make a Certificate authority and to generate exchange certificate, then you 'll deploy the certificates using GPO to your clients.
you can also deploy the followinf registry settings to force you clients using RPC/HTTPS:

HKCU\Software\Microsoft\Office\xxOulookVersionxx\Outlook\RPC DWORD = DisableRpcTcpFallback Value = 1

Replace xxOutlookVersiobxx by 11.0 for Outlook 2003 for example.

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