At launch I was genuinely excited about Shortcuts, having already used them back when it was still the Workflow app. Five years into Shortcuts being a first-party solution, they are so painfully unreliable that I’ve given up on them except for the most basic and non-critical things.

I invested a fair bit of time and energy into setting up some cool shortcuts initially, and it is cool what you can achieve with them – in theory. The effort required even for simple things is painful to accept as someone who’d be able to use an actual scripting language. Some of that can be overcome by pairing it up with Pythonista, Rubyist, Scriptable and similar things. Still you remain limited by Apple’s shortcomings¹ when it comes to versioning and syncing.

But I’d probably accept all that if the shortcuts themselves would reliably work. Sadly, almost all my shortcuts have stopped working over time. Mind you, not because of planned deprecations/changes in the actions I used with clearly communicated workarounds or alternatives. No, just random errors like in this screenshot. No explanation, no recourse. And it’s not due to updates – things just stop working from one day to the other.
Searching for something like that online at best will unearth an Apple Support Community thread from someone else having the same problem, where an incompetent volunteer sporting a “Triple Elite Question Hero” badge responded to suggest resetting your phone, Mac and router – and maybe also getting a different ISP or moving countries. If you think reaching out to actual Apple Support about a problem like this is a worthwhile endeavor, I would like to connect with you to discuss a bridge with very competitive pricing.

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My favorite shortcut was a “Clip it” feature for my own Plex server: It ran a Python script in Pythonista which connected to my Plex server’s API to retrieve the filename and timestamp of what I was currently watching. It then passed that data to a custom script on my server which executed ffmpeg to cut a 60s clip out of that file and returned it via HTTP. Shortcuts passed that clip into the trimming action and then the share sheet. A perfect way to share a good joke or other reference with friends quickly. It worked great, and it gave me joy every time I used it.
Until it stopped working – the trim action suddenly wouldn’t accept the videos anymore. Some cryptic error. Neither the iOS version, nor anything on my Plex/web server had changed. Since iOS is a toy, you have no good way of debugging yourself. Here I actually was able to debug a bit because things are partly happening on my server. I verified that (to the bit) identical video files that worked in the past are now inexplicably not accepted by the video trimming action anymore.

How could I ever again justify spending all the extra time to work around/against the already restricting and complicated nature of Shortcuts to get something like this set up, when it will just randomly stop working at some point?

To clarify – the error from this screenshot is a different one. From a far less complicated shortcut. In fact, I believe the “Make GIF” shortcut is a built-in one. It just worksn’t.™