Surely you didn’t kneel down to run it along the trailer under tubes ? If you did..I can now understand why you tried to make your life easier
However ..try running it over the transom..along inside the boat .. if you wish you can pass it under a thwart for extra security but I don’t bother. Pass it through the bow strop loop which ties the boat to the trailer then wrap it twice round the jockey wheel post which keeps everything tight so it doesn’t flap..and job is done.
Its even easier if you have a SIB with safety ropes along the tubes..just pass the cable through every second safety rope loop..it never falls off as it can’t.
Both methods take the same time as walking the length of the boat .. involves no bending or crawling along wet ground ...which is why folks are thinking you are making mountains out of mole hills.
And if you've somehow decided you don't want to go over a tube for some 'rubbing issue' then you still dont need to go hands an knees... it just needs looped behind the mudguard to stop it running the wheel...