My anecdata: this changed with age. At university I was disappointed that caffeine pills did nothing perceptible; and in my mid-to-late 20s I too could sleep well after multiple late espressos.

Now in my early 40s I feel the effects of coffee more directly (a physiological buzz if I have more than usual in the morning) and falling asleep and probably sleep quality both seem to suffer if I’ve not allowed a sufficient washout period - which now requires most of the afternoon and evening.