I think I got to 1942 once if my memory serves me right. I will always remember: I got sunk trying to pass Gibraltar into the med at night in fog, and got rammed by a destroyer. I think it is virtually impossible anyway with realistic settings as history says the attrition rate for U-boats was ridiculous and most of them died up to and before D-day anyway. Also you have to bear in mind the lack of safe port after D-Day would make the last year very difficult if you did anything but run and hide most of the time! I believe only a hand-full made it to V.E. day as active combatants.
All that being said I will keep playing SH3 until I do survive.
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