Monday, April 20, 2015

Apple Yosemite, iCloud & My Shit Don't Sync

Another day, another frustration with Apple's brilliant implementation of software. Today we have the next chapter in "Everyone Must Use Yosemite, possibly the worst implementation of Mac OS to get shoved down our throats". It goes without saying that I truly hate this version of the OS, but my dissatisfaction just keeps getting worse and worse.

As you may have noted from a previous post, I use 1Password software to manage my passwords. Since my first challenge during install, overall I've been pretty happy with the software. It does as promised and has operated without fail -- although typing your long master password into your iPhone consistently can be a challenge, but that's a user issue.

So I've been happily running 1Password on my work system, my home system, and my iPhone, but I started to notice an issue. As I began to look carefully at the list of passwords, I happened to notice that the number of passwords on my work system didn't seem to match the number of passwords on my home system. And yet, when I checked the sync settings, all of the settings appeared to be correct. Both systems were syncing to iCloud and claimed to have synced within five minutes of when I checked the settings. It says it's correct, so it must be correct.

Then one day, I went to perform an operation at work that I normally perform at home. After three attempted password entries using my work 1Password, I was locked out. After getting the system reset, I checked the password on my home system and discovered that it was different. Sync does not quite what mean what you think it does. I started to think about contacting 1Password's great customer service team, but I thought I might search for a solution before I contacted them. Unfortunately, I couldn't find a clear set of similar experiences easily and moved on for a bit. After all, if you're careful, you can manage this issue, even if you don't know what it is.

So one other issue with using 1Password came up as I learned more about the root cause of the sync issue. When your system restarts, if you're presented with a password menu -- like the login screen for iCloud and your iTunes password -- you don't have access to the password on your system until your system is up and running. Meanwhile, the geniuses at Apple (not the ones that work at the stores) implemented the Yosemite iCloud login such that, if you don't log in during that boot time, the installation and login fails. If you try to go back to iCloud through the control panel, it's too late -- your hosed.

As it happened, I discovered this error when I happened to have a written copy of my password with me during the restart process after the most recent system update. It then took me to the iCloud upgrade process -- which should be called the iCloud buster. It offers to update your iCloud, but with two choices -- if you don't update, none of your computers can share files stored on iCloud. If you do update, your computer that's running the old version of the software won't be able to share files with the devices on the new versions of the OS. Hobson's choice. Gotta love the new Apple -- way to do backwards compatibility.

It's not 1Password that is the problem, it's Apple's iCloud. My solution path is either I can update my work system to Yosemite -- but since I can't stand the stupid pastel transparency interface, I don't want to do that. Alternatively, I need to use a different method (like Dropbox) in order to sync my passwords -- essentially, paying to not use Yosemite. Right now, that's looking like the preferred option.

Perhaps the funniest part was right after I finished the Hobson's choice iCloud upgrade, the system presented a message that said, "hey, you've updated your iCloud. Would you like us to encrypt your hard drive and store the keys in your new updated iCloud?" Uh, yeah, no thanks. You've already done enough. Is is too late to reinstall Mavericks?

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