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I have one German sub near Canada and another near Ireland, both in hunt mode with 8+ supply, yet only the Canadian sub creates damage.
Did I miss a rule that only one sub may "hunt" on a given convoy route? Seems to me I recall the the surface raiders on "hunt" don't attack convoys if there is a sub on "hunt" on the same route?

Anybody have any experience with this or am I doing something wrong?

Answer: each may attack. A few turns after posting the questions the same wolf pack of three subs on the Canadian convoy all attacked.

If one has done all the damage possible against an enemy convoy, then the other won't raid, so it's best to spread them over various convoy routes if possible.