Saturday 6 September 2008

SBS 2008 - Use Outlook Anywhere (RPC/HTTPS)? RDC may need the same login format...

When we train our users to use their Outlook while connected to the Internet at a hotel or anywhere outside of the office, we make sure they login using the following format:

Username: domain\firstlast
Password: Give me that passphrase!

If our clients do not use Outlook Anywhere (Outlook connected via RPC over HTTPS), then they may struggle a bit at first with the need to use the above format to logon to their desktop via the SBS 2008 Remote Web Workplace.

That need will arise if the desktop OS they are running on the remote machine they are connecting with is Windows XP from what we have seen so far.

The other username format: FirstLast@Domain.

This situation is something to keep in mind when it comes time to train our client users after an SBS 2008 implementation.

Philip Elder
Microsoft Small Business Specialists

*All Mac on SBS posts are posted on our in-house iMac via the Safari Web browser.


Anonymous said...

Hi Philip,

If using Outlook anywhere from a domain joined laptop, you dont need to use basic authentication.

In effect changing to use NTLM they just open their outlook and automatically connects from anywhere.

You enable "Integrated Windows Auth" on the RPC directory in IIS, and then set the proxy authentication settings to "NTLM", Outlook then uses their credentials they logged onto the laptop with.

This assumes I read your post correctly, and people are getting the user/pass prompt when opening Outlook outside of the office.


Philip Elder Cluster MVP said...


Out of the box, SBS is setup for Basic Authentication due to the nature of the SBS setup.

IIRC, making changes at the level suggested on SBS will break things. Though, I could be proven wrong on that one! ;)

Thanks for the comment,


ottomatias said...

Kinda old discussion, but I can confirm that this repaired my configuration, which is Small Business server 2003. Exchange not working outside, but now, when I corrected the IIS for RPC over HTTP it does work. Also, NTLM works fine with no need to enter credentials after logging on to a laptop. With basic authentication, it does ask the credentials.