I have two leather sides from Acadia Leather that I want to cut on my Glowforge. They are lovely but I can’t get any masking, even high tack, to stick to them to save my life. Any suggestions?
I tried hunting through the forums but gave up after two hours. I have the high tack TransferRite Ultra and it doesn’t even stick the tiniest bit.
I think people use brayers…I’ve only used PG leather so far, and my problem tends to be more with getting the masking OFF after cutting. 
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For sticking masking to wood, I find that a light sanding with fine sandpaper will make it stick a lot better. Might help with leather, too…
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this. even just using the edge of a credit card would work. that’s basically what mine looks like.
this is what i use.
https://www.amazon.com/Lil-Chizler-Vinyl-Wraps-Decals/dp/B0065LTR98
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I did that with a burnisher I have and it helps a little with the initial stick, but I need to do two passes on this leather it seems and the masking blows off after one inside the GF. Feel like I’m missing something.
sometimes it can help to cover the material with a sacrificial masking layer, burnish, peel away to remove loose bits on the surface, and then lay down a fresh layer of masking.
leaving it masked overnight with a weight on top can sometimes help as well.
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Try a little heat, very gently with a hairdryer and follow-up with a squeegee/scraper card. Preferably on a test scrap first in case it sticks too aggressively. A felt squeegee is less likely to scrape things up: https://www.amazon.com/dp/B06XCSWK5S/ref=cm_sw_r_cp_tai_nT51CbBMBGCE5)
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Do you have to mask it? I find the smoke cleans off veg tan pretty easily. Although I’m just cutting and not engraving.
Not a problem for me either, but I dye everything I do black! 
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have you tried use a hair blow dry to softener up a bit ? 
Worth to try!
The problem you are experiencing might be the finish of the leather. I am assuming it’s not veg tan and that it probably has an oil or waxy feel. Problem getting any masking to stick to anything oily, I’d probably look to cleaning the leather 1st, might even need a quick wipe with alcohol if it’s a finished hide.
Update us with what you did, I am intrigued.