Slippage

I am using an eye bolt with a washer either side of the neck. It is secured with a wing nut.

Almost immediately after hitting the note and fully tightening the wing nut the rig loosens and drops the note back by a half step (think that the right term?). Example. G drops to F#.

Would a lock washer under a nut work better? How about a lock washer under the wingnut?

Tightening Direction.

Does it make a difference if I wrap the string clockwise or counter / anti clockwise?

Placement orientation.

Does it make a difference if the pegs are set in-line or perpendicular with the strings?

In my diddly bow I have the eye bolt screw coming into the neck at a right angle: the screw  goes through the narrow edger of neck.

In my three sting I have them placed vertically in the head: the screws goes through the wide side of the neck.

Is one placement superior to another for maintaining the desired note/ tension?

The diddly bow seems to hold the note better, but there could be other factors in play?

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As nobody answered I did a try with "Eye Bolt Tuning Pegs" on Google where you will find on cigar box guitar on one hour [choose Show All Items] a technical drawning. As you see from this, the pull of the string must tighten the screw. I would add a counter nut on the eye side of the bolt.

a little googling and I found an uncle crow CBG build

https://www.youtube.com/watch?v=Apm-M6JaTI4

you need an nut outside each of the washers to really squeeze the headstock for it to stay.

You need to wrap the string around the eye bolt so that it will tighten into the wing nut as the string tries to unwind. Also use a couple of pairs of pliers to tension everything up, using your fingers probably won't be enough.

it could also be a case of the "New String Blues" where a new string will relax some after it is first tensioned, partially due to the tension of the wraps around the tuner evening out the tension, and partially the string stretching under tension.  It takes a couple of minutes of hard playing retune hard playing retune etc til the strings finish relaxing.

Eye bolts is all I have ever used and have not had much of a problem with anything coming loose. As JL pointed out, it is important to have nuts on the outside of the washers at both ends so you can clamp it tight to the headstock. It doesn't hurt to use a locknut (nylon insert type) on the eye side of the bolt so you only have to worry about tightening or loosening the one side with the wing nut.

What I missed was the nut on the side opposite the wing nut.

It's the build video but I missed it.

Makes sense

So much to take in the first time, blush.

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