I'm forced to use Outlook 2003 by a clueless IT department -- forced, in fact, to sit an entire separate ThinkPad next to my iMac just for email, since a Mac can't possibly sit on the trusted network. It's a security threat, after all. Unlike Windows. Which is secure.
Having used GMail for years, I'm shocked at the sheer unfriendliness of Outlook:
Searching takes minutes, and only barely works.
Perhaps due to way Exchange is configured, Outlook won't auto-complete contacts by first name, only last, and even then it only auto-completes names from my personal contact list, not names in the Exchange directory.
Threading. THREADING. I had threading in 1998 using Mutt, a command-line email client. GMail has had threading since day 1. An email and it's replies form a dialog, obviously, and Outlook's failure to group those emails into a thread makes it about as useful to me as my Nokia 3510's SMS functionality was.
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