On further investigation, I actually overestimated HLW's time "at the front" as he took command of U-5 in Dec 1939 but did not begin the first combat patrol until April 1940.
I would guess that 2-3 years was the longest any one man served as an active frontboot commander - simply because those that were already in that position early on (if they weren't killed or captured) had in most cases been transferred and/or promoted to other duties by mid-war, and those that began their commands mid-war or later either didn't survive that long or couldn't serve longer if they did because the war ended.
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