Hi Casey
All missions are date sensitive.
It is not compulsory to request a mission I never use it as the black icon will show you the patrol area.
If you now start your mission without requesting it from the Flotilla Leader and head over towards the East Coast the mission will come up on your Navigation Map followed by Breaking the Fortress special mission.
Baltic 31/08/39 to 05/09/39
EBCW 04/09/39 to 01/12/39
BTF 10/09/39 to 15/10/39
Just be aware of the narrow time span on BTF
See my tutorial post #64 for a full list of missions
http://www.subsim.com/radioroom/showthread.php?t=211804
Peter