I guess what they're suggesting is to compromise the server in such a way that it does not send "delivered" receipts for any messages anymore (even though it actually delivers them to Bob, and Bob answers, and a "normal" conversation ensues).
Then, at some point later, Eve on the compromised server could send a "oops, here's a new key, send everything undelivered again" message. Then, the client, as it is now, would just re-encrypt and re-send all those messages it deems undelivered so far (and then pop up the "key changed" message, if you had requested it in the settings).
You'd recognise the attack by seeing only single ticks on messages, even if Bob had seen them and answered.
Then, at some point later, Eve on the compromised server could send a "oops, here's a new key, send everything undelivered again" message. Then, the client, as it is now, would just re-encrypt and re-send all those messages it deems undelivered so far (and then pop up the "key changed" message, if you had requested it in the settings).
You'd recognise the attack by seeing only single ticks on messages, even if Bob had seen them and answered.