Ive been able to get close on the surface (at night) but usually make all my attacks submerged anyway. It seems harder to do surface attacks in SH4 then it is in SH3, maybe its because they subs are so much bigger (a german VII is quite small compared to US fleet boats for example).
Also remember to keep your speed low. The AI can spot you if you're putting up a big wake, which is realistic... Nothing like a big trail of white frothy foam on a dark calm night to give yourself away. Also, keep your profile low, meaning dont show the convoy/ship your side profile, try to keep the bow pointed towards the ship so you're presenting as little of your profile as possible, you might even try going in decks awash.
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