I've never had that much trouble penetrating a convoy, even in 1944-45. I usually try to get ahead, staying out of radar range, get into rough position then dive. Once I see the convoy on sonar, I go to silent running, ahead slow and get myself into position. Once I see the first escort I try to position myself to either side, keeping a careful watch on his zigzagging. Once safely pass, I point myself perpendicular to the convoy. Look for the tankers, shoot from the furthest possible point, which gives me a couple of options.
I can see what the escorts do, they usually head away from the group. It also makes the convoy zigzag which is good as that slows it down, allowing me time to reload and get more shots off. If I am detected I head into the middle of the convoy which helps to evade. If I am not detected, I can shoot more tankers or if the zigzagging pulls me/or ships out of position I move out of the convoy shooting more ships as I go. This makes a hole which can allow easier penetration next time.
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