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2) I haven't been able to get PocketInformant 8 to be recognized by MobileShell
It recognises it as a stand alone application - do you mean that it doesn't use PI8 as the default app for Calendar/Contacts etc?
Correct. At least in the earlier version of Mobile Shell, alternate PIM programs could be loaded into the organizer screen as alternates, and the Now screen could map to the altnerate PIM instead of using the built-in.
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There is a seperate CAB install for enabling PI, Agenda, etc. The link is in the FAQ.