For a long time, Apple’s built-in text replacement system has been unreliable at best. A few months ago Brian Stucki went deep on the problems with Apple Text Replacement, and it got a lot of attention on the Internet. In my mind, the inability to synchronize text expansion snippets was one of iCloud’s biggest black eyes … for years.
Anyway, all this attention appears to have led to Apple letting John Gruber know that they were aware of the problem and in the process of fixing the underlying iCloud sync for text replacements and promising that things would get better soon.
As of this morning, Text Replacement syncing is working immediately across my Mac, iPad, and iPhone. This has never worked reliably for me in the past. In the past, I've reset (and even nuked) my devices trying to get this feature to work to now avail. I had to grin a bit as I was looking at the now-syncing text snippets as so many previously lost snippets were resurrected. There about ten separate “test” snippets as I'd tried over the years to get this to work. Also, I had one snippet that refused to die. It was the phone number I had for my old law firm. I haven't worked there for over two years, and the snippet would still fire off despite my best efforts to kill it. Today I deleted it, and it vanished from all devices instantly.
You may ask now that we have working text replacement from Apple, do you still need something like TextExpander. I certainly do. Take this as you will since TextExpander sometimes sponsors my podcast, but TextExpander still runs circles around native text replacement. Autofill, date and time tokens, Tab keys, rich text, and images are just a few of the reasons why I still use TextExpander for most of this stuff. Nevertheless, it is nice that Apple finally got this sorted out.