There seems to be something odd with the requester chest, but I'm having trouble reproducing it reliably. At certain times it seems to get "stuck" and won't fulfill any further requests.
I've played around with different arrangements (unavailable/unresearched items in the list, gaps in the list, etc.), but can't figure out what the trigger is.
Image of a "stuck" requester chest (check the right-hand overlay to see that some of the requested items are, in fact, available):
https://i.imgur.com/UPq3oJo.png