It’ll only trigger when the template changes from false to true. As the attribute is already on the current day, it starts off being true so won’t trigger this cycle.
Personally, I’d write it thus (although this still might not trigger for today, depending on how that sensor operates):
Triggers when either the attribute or the current date changes (one minute into the day to avoid potential race conditions; or you could set it to when you want the notification); then checks if the attribute matches the date before continuing.
If you desperately want it to trigger today, add another trigger to my version above:
That’s make sense. I tried changing the attributes via developer tools and I got the notification! Thank you!
I also set the update interval for the rest sensor to 100000s and then created another time automation to update the sensor manually every day at a specific time.
Bit fiddly, but I think this will work. You might get a double notification on Friday when you have paper and mixed due: if that is a problem we can sort that out.
Last line gets a list of attribute keys whose value is the current date, converted to Title Case and joined with commas if there is more than one that matches.