I’m a fan of iMessages the same way I was a fan of BlackBerry messenger when I was on that platform. Who doesn’t like free text messaging (without having to run a separate IM app on your phone)? The iCloud integration promised to deliver what I had predicted, but I’d never gotten iMessage delivery to work on both my iPhone and iPad, let alone on the desktop via the new Messages beta.

I was one of the folks who had previously used MobileMe (it was the best solution I found for contact sync). I also had a separate Apple account, with a different login. Inspired by the promise of unified messaging on my phone and my computer, I started digging into who this wasn’t working for me.

As I’d suspected, the problem seems to have been related to the different “Apple” accounts I had. I had “upgraded” my MobileMe (me.com) account to iCloud, but I hadn’t “upgraded” my other Apple ID to iCloud. My iPhone, iPad and the Messages beta on my laptop were all initially using my non-MobileMe Apple ID. This likely would have worked if I had “upgraded” that account to iCloud, but I choose to take the easier route: sign-out of all devices and sign-in under my iCloud “upgraded” MobileMe account.

With this change, everything is finally working as expected – I get messages on all of my devices and can reply from whichever is most convenient.

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The only additional item worth noting is that I’d associated an email address with my Apple ID that I now wanted to connect to my iCloud/MobileMe account instead. My initial attempts to do this resulted in an error message indicating that the email address was already in use by another account. It was not readily apparent how to disassociate the email address with the Apple ID; turns out you can do this by logging in to your account on apple.com.