Given the 40mm height of your box , wonder what its other dimensions are , fairly small ?
Also how much space is taken up with the electronics and are any of them likely to generate any heat at all ?
What kind of outdoor min / max temps are we talking about as you do not show a country flag.
You will never avoid some condensation etc, so where possible use a protective lacquer coating on your board instead .
Unless your cable is going to be tugged or moved around a lot, a simple rubber cable gland is all thats needed, or just a hole and the cable bedded with some silicone rubber sealant.