May 5 2021

Password Insanity

My mom is extraordinarily patient.

Several weeks ago, I bought her a brand new Mac as a mother’s day present. She was using a 2010 Mac, and it was time for her to use one that didn’t have an endless spinning pinwheel of Mac slowness on it.

I had it sent to me, although there’s a whole story in just that. I set it up, downloaded and set up all the apps she used, installed all the new stuff she needed to manage her passwords from now on, connected iCloud, and tidied and buffed it. Then, I figured we could use Zoom’s remote control, so I thought all I’d need to do was ship it to her, spend a few hours with her walking her through everything, and she’d be in great shape.

I can be so naïve. And, since I’m no longer young, I don’t qualify as young and naïve.

She and my dad got it, set it up, and connected it to the new LG monitor I’d gotten her along with the Anker USB extender. Cables and connectors – lots of them. It’s kind of remarkable how hard Apple makes the transition from devices (iPad – different cable, 2010 Mac – different cable, 2020 Mac – different cable, connect old external hard drive – different cable.) So many cables.

Eventually, it worked and, after walking through giving Zoom access to the right things on the Mac (click on the little lock in the bottom left; now check the box next to Zoom; no, the one next to Zoom. Yes, Zoom in the window to the right of the lock…) I was able to connect remotely.

Day 1 was fine. We spent three hours Sunday afternoon going application by application. I copied all the files on her external hard drive (which she lovingly calls “her Toshiba”) to the new Mac. I enabled iCloud to upload all the files to the cloud, and we spent a bunch of time discussing why that would probably take a few days over their slow internet connection, but then everything would be on her computer and in the cloud. We tested all the apps to make sure they were pointed at her documents as a default so she could find them. We went through the approach with the new password manager, which means she has three different passwords, one for her Mac, one for iCloud, and one for the password manager. But, once she has these three memorized, she won’t have to keep the rest of her passwords for all her individual apps “somewhere.”

We had a short discussion Monday night to refresh a few things. Last night was the first day of working through the list she’d made during the day of issues and questions.

We spent three hours on issue #1. Passwords.

It should have been simple. I foolishly made the Mac and iCloud passwords the same, figuring that would be easier for her. But, after Apple let me do that, it eventually told her she couldn’t have them be the same (hours later) and prompted her to change the Mac password. She wanted the Mac password to be a different one, so I assumed all I needed to do was change the iCloud password, then the Mac password and all would be good.

Two-factor authentication slowed that down. She has an Android phone, and the authentication is on her iPad, but that took me a while to figure out. I think we entered a different TFA code a dozen times over the course of three hours on her iPad. Then, I thought we were all set, but suddenly the Mac password didn’t work. And just like that, we were logged out of the computer, and Zoom was disconnected.

150 minutes of misery ensued. At the two-hour mark, I said, “just ship the Mac back to me, and I’ll start again.” Mom really didn’t want to do this or have to start from scratch, so I pressed on with a full password reset using iCloud. But, of course, the iCloud password was now no longer working. I have a feeling that Apple, in the background, invalided both of them somehow, but what really happened is still a mystery to me. The big hint was the endless “You have been locked out of …” message on iCloud and the regular prompts on the Mac to use iCloud to reset your password. Um – ok.

And, you guessed it, Zoom wasn’t able to connect us while she was logged out of her Mac, so this ended up be me dictating what to type, with her taking screenshots of her Mac screen and texting them to me since she was an on Android phone and we couldn’t simply Facetime.

Eventually, I figured out that I could reset her iCloud password on her iPad, which was still logged into iCloud (thankfully, I didn’t say “log out all devices from iCloud” when prompted over and over again. So we did that (more screenshots), we then did a full password reset on the Mac using iCloud (I never knew that was possible) and re-entered a new Mac password.

Three hours later, she got back into her Mac. We were exactly back where we started. Except now she was getting a message that the Mac couldn’t log into iCloud. Launch Zoom. Connect. Grant remote access. System preferences. Apple ID. Log out of iCloud. Log back in. Reboot (oops – bye Zoom). The bad message was still there.

Well, at least she can get back into her computer.

I’ll take on that last error message again tonight. And try to get to item #2 on her list. Maybe.

We all know the current approach to passwords and security is completely busted, but I just lived three hours of how incredibly broken it is.

And, before you say “just use the Touch ID,” neither of our fingerprints work. It’s not just Apple, it’s Clear, Global Entry, and the fingerprint process for a money transmitter license, so there must be something genetically wrong with us. Plus, I’m pretty sure that would have just made it worse somehow.

Mom – thanks for not chucking the new computer out the window and going back to your old one.