For reference, this is the Sean Spicer photo I'm using.

On my test pumpkin I tried to engrave his face using several layers. In other words, the lighter the color in the photo of his face, the more times the laser would hit that pixel. Therefore, the pumpkin would be engraved deeper there, letting more light through. That was the idea, at least. It didn't work too well, and resulted in the Frankenstein-looking face you see in the photo:

Maybe it looks better illuminated? Not really:

I mean, you can see the contours, kinda, but it doesn't look like Sean Spicer.

So I next tried to trace his face both automatically and by hand, hoping to do vector cuts (faster to run, too), either partway or all the way through the wall of the pumpkin. However, well, see for yourself:

Not really usable. Unfortunately, this was the night before the first day of Maker Faire, and I ended up helping with some friends' projects, so I didn't have anything to show. Sometime in the last couple of days, possibly on my way to the Faire,* I had the idea of trying halftone.

*I'm super tired right now from trying to finish this project and from helping with other projects, so I can't remember when I thought of it.

I decided to try for the second day of Maker Faire, with the Pumpkin Spicer MVP (which consists of the engraved pumpkin and the pumpkin spice scent—I actually only thought of adding the soundbites a week or so after I first had the idea). Also, the Faire is being held in a horse barn, so the pumpkin spice would make Protospace's booth smell nicer.

Pixlr can do halftone reasonably well. I scaled up the image first (by 3 and a bit times), then applied the halftone filter with size 6, multiplier 10, no add, yes invert. Then I saved it and opened that in Paint to convert it to 1-bit BMP (which is what the laser cutter likes). The result:

I don't know where the outline came from, but I guess it's OK. Test engrave on a sheet of paper (too much energy density, but it shows that it works):

I'm not sure that looks like him, and it's a bit big for the pumpkin, so let's try again smaller and with a lower power setting:

I guess that looks enough like him. The banding seems to be moiré caused by scaling down the halftone image in the laser cutter software. Nothing I can do about it tonight. Now to prepare the pumpkin…