Originally Posted by Pickles

1:55 to exit Haneda is way more than plenty, you'll be fine, probably end up taking a much earlier monorail. As for your departure, I don't think there is a 4:58 AM monorail, and if there is, is probably a local, don't bother with that one. There is an express at 5:11 AM which is plenty of time for the AA JFK flight at 6:55 AM.