When on the surface there are things to remember..
- Is the Moon up and shining (moonless [no light] nights are better)
- Is the weather clear, cloudy or misty (obvious)
- Are the seas rough or smooth (Harder to see in rough weather)
- What speed are you travelling (higher speed makes a visible bow spray

)
- At what bearing is the escort (Same as sonar detection.. you can be detected easier if you're side-on, more sub to see).
Minimise all of these and you're a

sub captain, sneaking right into convoys, undetected.