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Headstock decal isn't right

As one who has been doing guitar refinishing for 20+ years, I have to ask why you are using Truoil if you are going to poly it. I've never found mixing finishes to be a good idea. Delamination is one of the main reasons. If it were me, I would sand ALL the finish off of the headstock, re-stain, apply poly, apply decal and finish with more poly. Less chance for any problems IMHO.
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Another option totally separate from all the discussion of finish and top coats to consider.

Find someone that has a cricut machine. My daughter made two custom stickers for me to put on headstocks of my parts-basses. The cool part of these is that they are made so you remove the backing, apply it put some pressure on it to lay flat, than remove the top clear cover so the only thing that remains is the white lettering. No outline left behind, no tedious cutting around it.

I painted the headstocks, applied them, cleared over them and they've been good.

Lots of home artists, craft people have a cricut too. People use them to make custom mugs and window stickers, etc. Maybe finding one of those people and asking them to just make the sticker for a fee?

Just a thought that might be helpful.

Cricut machines, in case you aren't familiar with them Cricut Shop: Your One-Stop Destination for Cricut Cutting Machines, Heat Presses, Materials & More

She made the stickers on the red and blue ones.

headstocks.jpg
 
+1 to having perfectly level glossy surface on the headstock before applying the waterslide decal. +1 also to cutting it as close to the letters as possible before applying. Otherwise you will get the cloudiness and visible edges that you're seeing. I know this from experience during my build last year. ;)
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As one who has been doing guitar refinishing for 20+ years, I have to ask why you are using Truoil if you are going to poly it. I've never found mixing finishes to be a good idea. Delamination is one of the main reasons. If it were me, I would sand ALL the finish off of the headstock, re-stain, apply poly, apply decal and finish with more poly. Less chance for any problems IMHO.

Why? Because I don't really know what I'm doing and I was too impatient to ask before I dove in. In my defense, I had searched for "waterslide decal over Tru-Oil" and found a couple places that said it was OK. Thanks for your input. I'm about to have another go of it. Updated post to follow.
 
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I appreciate everyone's input. Here is where I currently stand. I sanded the headstock to 180 per the photo above. My 1st question is: Do I need to sand any further?
My plan is to re-stain, let it dry, then spray a couple coats of poly, sanding with 2000 or 0000 steel wool (?) after each coat. Then apply the decal, let it dry, then finish up with a few coats of poly.
Good plan, bad plan? Open to suggestions. THANK YOU!!!