I try to explain how to set up outlook anywhere (with SBS 2011 , exchange 2010, office 2007).
1) get SBS's CA certificate and install it to client computer.
in SBS go to:
start -> administrative tools -> certification authority -> mydomain-myserver-somthing -> issued certificates -> go to Web Server certificate -> Open -> certification path -> 1ST node on tree (that is CA) -> View certificate -> details -> Copy to file -> next -> der encoded binary
3) transport that .cer file to "client" computer (where you want to setup outlook anywhere client). open it there and install certificate.
4) read here #4 http://blogs.technet.com/b/sbs/archive/2009/06/19/common-remote-web-workplace-rww-connect-to-a-computer-issues-in-sbs-2008.aspx
Most idiotic thing, and the reason you might fail to setup remote outlook , is that in outlook account settings Microsoft exchange server must be its local name. That is name you see when you type Get-OutlookAnywhere in exchanges managmend shell.
E.g. go to
Contol Panel -> mail -> email accounts -> Change (existing exchange account) or New ->
and now you got:
Microsoft Excahnge server: mydomain.myblalbl.local
User Name: mydomain\myuser
now click more settings:
in Connection TAB:
Outlook anywhere: Connect to Micrsoft Exchange using HTTP - check it
click Exchange Proxy Settings
enter your server DNS (not it must same that you have valid certificate for)
NB! check only connect to proxy servers that have this principal name in their certificate
enter there: msstd:yourdomain.com
check both: on fast network and on slow network
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