Reader Darlene Brian is having issues with her iCloud account. She writes:
I use Outlook for Mac for my email and today it's been telling me that my iCloud account isn't authorized. I've entered it multiple times and it still won't work. I've tried other third-party apps that use iCloud and am having similar difficulties. Any idea what's going on?
If I had to guess I'd say that you have implemented two-step verification for your Apple ID. As of October 9, 2014, Apple requires that you generate app specific passwords for third-party apps that use your iCloud data. This includes apps such as Outlook and BusyCal.
In order to generate one of these things you must go to Apple's My Apple ID page, click Manage Your Apple ID, login, verify your login through the two-step process, select Password and Security, and then click Generate App-Specific Password. You'll be prompted to name the password (you could call it Outlook, for example) and then you'll receive a 16-character password that will work with one of your apps. While you're there you'll want to generate more passwords for your other third-party apps. How inconvenient you find this depends entirely on the number of non-Apple apps you use that interact with iCloud.
At the risk of editorializing, I'm torn on this effort. I understand that Apple wants to do everything it can to make iCloud secure and I applaud that effort, particularly as hackers get more expert and Apple steps ever more into the financial arena.
But I faced the same situation earlier today where apps that worked yesterday were nagging me for an iCloud password that didn't work. Rather than deal with the bother I simply turned off two-step verification. I understand that I'm not a paragon of patience but I fear that others will do the same thing, thus leaving their account less secure than it was before this policy was implemented.