Silent Service on the Amiga (which is the definitive version where you may encounter proper warship convoys) still holds up surprisingly well. It may not have as many features as Silent Hunter or AOD but the realism is still high enough* to make the gameplay convincing from a tactical point of view. It also has some design elements that make it a better game than any other sub sim like the strategic transit map that allows you to get to the action quick without having to fiddle around with inadequate time compression like in SH.
*Not counting the deck gun that allows you to fire as fast as you can tap the G key, lol.
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