It's quite a pain even on a Skipjack, given once they start fleeing, the ships never slow down again. Convoy attacks are rather frustrating in the 1968 campaign because of this: with a body of merchants and some escorts on the flanks, it's usually very difficult, if not impossible, to conduct a damaging enough first strike.
I haven't done many of those missions (invasion force interceptions) in those conditions, but so far I tend to tangle with the escorts first and then, once it's safe, I speed after the merchants. It's unfortunately rather boring, considering how they slowly spread out. Eventually you end up with targets 30+ KY apart and you still have to get very close to land a good hit. After taking down two or three vessels, the other ones become too laborious to find unless you're willing to travel at 50 ft, frequently popping the radar, and time-compressing for a long while. You can usually kill enough to accomplish the mission, but it's not really fun, in any case.
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