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It annoys me to no end:

Is there a way to directly sync Windows Live Calendar with the Windows Mobile Calendar? With directly I mean without using outlook, since this needs to work without ever connecting the smartphone to a computer.

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Microsoft added ActiveSync support to Live Hotmail, so now syncing is no problem anymore (but since windows mobile 6.x is old news nowadays it doesn't matter much anymore).

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Microsoft's MyPhone sounds like what you're looking for:

http://sn1-p2.myphone.microsoft.com/mkweb/MoreInfo.po

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I thought MyPhone is mainly to backup my phone. I see no mention in the description about MyPhone being able to sync calendar data to windows live. The only mention of windows live is about being able to upload pictures. You sure there is any cal sync functionality in MyPhone? – Sam Jan 13 '10 at 13:46
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My apologies, it seems MyPhone will backup calendar appointments but not synchronize with windows live, when I used MyPhone I also synced through outlook. "What type of information can I back up? The recommended (default) settings will synchronize your contacts, calendar appointments, tasks, photos, videos, text messages, songs, browser favorites and documents between your phone and your My Phone web account." – ChrisFletcher Jan 14 '10 at 13:01
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