Dacian,
thanks for your responce and the picture of the strain relieve on the Cat 5.
Slightly unsure why the TE- Connectivity 966066-2 should fit.
If I am reading the Phoenix connection data sheet correctly, it shows that the insert diameter is 1mm diameter?
The 966066-2 you mention above is 1.05mm outside diameter( drawing link below).
Anyways -I'll order some of the 966066-2 and give them a try. Maybe when crimped it will fit?
Also, according to this drawing the 966066-2 is made for 23 AWG? So maybe I'll just use CAT 5 / 6 stranded.
Your comment that if the solid core fails due to vibration it will fail open will certainly save your battery but it will also mean you lose power on board. On a sail boat in storm with autopilot engaged that can be a very dangerous condition.