Outlook 2010 calendar won't sync with Android phone

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Outlook version
Outlook 2010 32 bit
Email Account
I'm using Outlook 2010 on a Lenovo ThinkPad running Windows 7 Professional with Service Pack 1. I sync my calendar and contacts with my Samsung S6 Android phone using Outlook Connector and a Windows Live account. Suddenly today, my Outlook calendar syncs with the Windows Live calendar, but not through to the phone, and the changes I make to my phone calendar don't even make it to Windows Live. Any idea what the problem could be?
If it's sudden, it could be server side issues, although it's strange that it works on the desktop and not on the phone - you'd expect it to not work on both. It sounds like the problem is on the phone, since new items there don't sync up. First the obvious question: are you using the correct calendar on the phone? did you hide the outlook.com calendar? If that is not it, try removing and re-adding the account on the phone.
Yes, I removed and readded the account on my phone, and it seems to be working, at least for now. Unfortunately, of course I lost all the calendar items that were unique to my phone.

I've been having issues on and off with this setup (Outlook Connector through Windows Live account), and I'm afraid that if I upgrade to Windows 10, things will only get worse. Do you have any advice as to what the ideal setup would be for someone like me who is a PC user, wants to use Outlook for personal calendar, contacts and Yahoo email, and needs to sync with an Android phone? I'm willing to get a new laptop and version of Outlook. Thanks.
Outlook.com is moving to office servers - which means Exchange server backend. Once that happens, everything should work great for you - it'll be set up in outlook as an exchange account and on the phone as active sync (but because it's on exchange, it's a more robust version of active sync).

They started the migration but i don't know when they expect to be finished, they are saying it should be sometime late this year or early next year, but I can't guess as to when your account will be moved. If you get an email or a popup when you log into outlook.com asking if you want to move, definitely accept it.

If you need a new laptop, i would definitely upgrade outlook - but outlook 2010 is fine and will work when the account moves. I don't think upgrading the desktop will cause problems - it sounds like the problem is on the device side, not on the desktop/laptop.
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