The debate continues, is BlackBerry better than Windows Mobile. In the end, both phones provide loads of features packed into a compact device that can be carried anywhere. Phone service, email, calendar, contacts, games, Internet browsing (albeit somewhat limited), camera, music, and the list goes on. So, from a feature perspective, beauty is in the eye of the beholder.
However, when it comes to the ability to synchronize phones with one's email, contacts, calendars and tasks, one truly shines above the other. Windows Mobile, in my opinion, wins this competition hands down.
The simple explanation is that with BlackBerry one must install BlackBerry Server software on the Windows Server. This is free for one phone, but can be very costly for multiple phones. The only alternative to this is to physically connect the phone to a PC in order to get calendar and contact updates. Mail, by the way, doesn't require either, but does get routed through BlackBerry's server which is subject to outages.
Windows Mobile, on the other hand, requires two things to receive email, calendar, contacts and tasks. It requires a certificate from the Windows server (free and easily generated), and it needs to be set up. That's it! All that said, if you're company doesn't have an internal mail server and you're receiving email through your Internet Service Provider, i.e. RoadRunner, then both phones are equal.
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