@Riley_S I've tried deleting and remaking the routine. I've also tried rebooting the switch. I'm fairly certain I did set these up using Matter (part of the reason I went with these switches). I agree that it's probably something in the Alexa side/Alexa skill side that is the issue. I just created a new routine that whenever the switch is turned on, Alexa should say "Happy Birthday". The new routine didn't work; when I turned the switch on (by voice, Kasa or Alexa app, or physically) the routine wasn't triggered. I can control the switch from the Kasa app, the Alexa app, or physically  and it shows the correct switch state in both apps at all times.

I confirmed this is only an issue with the two KS225 switches I have. The KS205, ES20M, and HS210 switches will correctly trigger the routine and get the "Happy Birthday".

Found some more interesting parts now. These routines worked fine from roughly June of this year until a couple months ago. There were no changes (no new switches or anything else done between the time they were working and when they stopped). I have this narrowed down now where both rooms have a KS225 and a KS205 in the same switch gang. This routine does not work if either the KS205 or KS225 is the switch that is to be detected as on to trigger the routine. Nothing has been changed and this had been previously working, and in would expect if this was sudden hardware failure (for both at the same time), that it would also not be able to correctly detect the switch states in the apps. The routines work for any other device being detected as the one being the 'On' trigger, just not the KS225 or the KS205 in the same gang.