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Is the Driod able to snyc with my existing calendar on Windows Outlook or should I be looking at a Windows OS phone?
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Yes, the Droid does that. You just need to set it up in the corporate calendars app thing.
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For those of us who use a stand-alond Outlook (not connecting to an exchange server) -- is there something like "Wireless Sync" that Windows Mobile users have (it's on the desktop keeping all my contacts, calendar, tasks, email up-to-date on my smartphone) ?
Or, is there some other workaround to do the same thing (if we're not on an Exchange server) ?
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You can sync your Outlook to Google Calendar, then that will sync with your Droid. Download the google calendar sync tool.
To sync contacts, use Funambol. It will sync Outlook contacts to gmail, then your phone syncs with that.
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OH, and NitroNotes will sync notes. I haven't found anything to sync tasks reliably yet.
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Yes you can actually enable your settings on your google account to synchronize everything from email, calendar, and notes also. You do not have to download any application for this either. Hope this helps.