I have just discovered that Rolo can open the cat flap from the inside when it's set to entry only; he hooks the rubber edge with his claws and lifts the flap inwards, then squeezes through the gap. The sneaky little bugger! I've seen him pawing at it before but just thought he was being a bit stupid and forgetting how to use it properly...
When both boys are in for the night I put a box in front of the flap so they don't bash at it, but Rolo came in first tonight after 'cat curfew' before Monty, then five minutes later was back out again. This explains why my cat sitting friends thought he'd gone missing after not seeing him for several days the other week - they couldn't block the flap up from the inside, so setting the flap to entry only when they visited kept Monty in but not the smaller, sneakier one.
This is just a basic four way entry standard flap - I can see I may need to invest in something a bit more hardcore or high-tech to defeat his tricksy ways. Has anyone else found a way around this?