Chris Wiegman Chris Wiegman

iCloud Keychain is Less than Reliable

One of the reasons I stick with Apple devices is that its ecosystem is the only way to get truly seamless integration between all my devices.

I’m not talking about things like KDE Connect or even Google Services where notifications and other things can sync if the right apps are open, but truly seamless integration where there is absolutely no reason I ever need two devices near me at any given time.

If I get a phone call I want to be able to answer it with my laptop, or my iPad or my iPhone.

I want to reply to text messages where I’m at, when I get them, without having to find my phone.

The list goes on and on and on.

I was looking for this type of integration even well before iCloud was a thing, hacking together Dropbox and other apps to get as close as I could way back in at least 2007. Even my Twitter account was an attempt to be able to more easily use Facebook (yes, I did use it in 2008) from my phone.

Nothing frustrates me more than having to reach for another computing device when the device I have available is perfectly capable of the task I need to accomplish. As such, during the day I live on a MacBook. After work, if I’m not coding, I switch to iPad and when I leave my house I take my phone and each of them can almost do everything I need.

Sure, there’s been some regression here the past few years. As companies abandon the desktop there are things I can’t access anywhere but my phone. This is, for the most part, what I almost universally stick with native Apple apps whenever possible. For me they usually just work.

The biggest issue I have with Apple these days is iCloud, specifically iCloud Keychain.

It’s no longer uncommon for me to open any given device to see an alert on the others that the device I just picked up, which had probably been sitting for a few hours, has just logged into iMessage or another part of my iCloud account as a “new device.”

About once a week I have to, at a minimum, reboot my devices entirely as something with my iCloud credentials with the keychain will become corrupted and it won’t be able to access a service at all. Sometimes it’s messaging, sometimes it’s FaceTime, sometimes it’s Music… the list goes on.

If I’m lucky the reboot will work. Often times I’ll have to reset my iCloud login as if its a new device or even reset the device completely, something that seems to happen about once a month.

The biggest sign of issues, my laptop will stop being able to unlock with my Apple Watch. When I look in settings I’ll see “Apple Watch” instead of the watch name and I know I’m in trouble. Then I’ll go through deleting a dozen or so entries from the Keychain and a few files and… hope for the best.

Logins and auth are so fundamental to using Apple these days. That Keychain has gotten so horribly unreliable makes it all so very, very frustrating for me. I lose, at a minimum, probably 30 minutes a week to the issue and, if I have to completely reset a device, can easily lose up to 3 hours or more in a given session. That should never be the case.

It frustrates me enough that I have considered going back to Android but that had its own set of shortcomings that I don’t want to get involved with either.

I guess this is a big part of why I feel like I can never have nice things.