@Emil - it’s when the Alexa app on my phone gets updated.
I use flic along with an Alexa routine to turn a smart plug on/off via Smart Life skill in Alexa.
So as I see it, the sequence is: flic button talks to flic hub, flic hub talks to Alexa, Alexa talks to Smart Life, the smart plug goes on/off.
When it fails, I use the half-split approach to debug, and from Alexa I can turn the Smart Life plug on/off, but flic can’t. So that tells me that Alexa to Smart Life is working. I watch the LED on the flic hub turn on off in response to flic button press, so that part is working.
That only and logically leaves the integration between flic and Alexa at fault. And if I delete all that config, and re-add it, it all works. So that tells me that nothing physical or irreparable is damaged.
To me, this appears to be a software integration issue.
My iPhone is from 2020, has lots of space, and is running the latest iOS. My network is all gigabit with managed switches, WAN is gigabit, flic hub is wired Ethernet, and my WiFi is 802.11ax from 2021. None of my Alexa devices complain about connectivity. And from Smart Life app, the smart plug works fine every time.