If you type the game's name into Google, one of the search suggestions is the title of this post. I myself had gotten all the endings and was only missing this one illustration, and finding absolutely nothing to go off of on the internet, I set off on my journey to find it. As a result, I don't know exactly what triggered it, but I do have it now, and I have a pretty good idea of what might need to be done to get it.
Oh and fair warning: I'm going to talk about the end of the story in this post, so if you haven't already played the game and seen all the endings, maybe don't read further. Your call though.
I started by noting that the illustrations in the gallery are in the order in which they appear in the story. Illustration 26 is the one where Syrup goes to sleep after seeing what was recorded on the crystal ball, and illustration 28 is from when she goes to return the crystal ball and has a chat with Toffee before going to sleep. I figured it had to be somewhere around that specific point in the story.
My first step was going for Gumdrop End and experimenting with different choices on Mt. Sorbet, but that got me nowhere. My next idea was to get Pastille to show up on Mt. Sorbet. It had been a few days and I kinda forgot what I needed to do for that. As a result I got Frozen End a few times. The gist of getting Pastille End is: be nice to Gumdrop and tell Pastille you wanted to help him (when given the choice to supervise Gumdrop, help Pastille, or leave), then let Gumdrop disappear but help Pastille find her. I forget if choices matter on Mt. Sorbet before telling Butterscotch you hate her in order to stay trapped in the cave. If you end up in Treat's cabin, you're on the right track, just avoid getting the Worst End and you'll be good. Once you're down off the mountain and have the crystal ball, look at it before going to sleep.
Anyway, I got Pastille End. Then I remembered that Toffee End has a slight difference if you get it again, so I went and got Pastille End again, but this time Syrup had some new dialogue after seeing the scene in the crystal ball. After this, I got the elusive illustration 27.
This was technically my third time getting Pastille End, but it was also the second time in a row getting this ending. My recommendation is simply to keep getting Pastille End, and eventually you should get the illustration. If you need to, play around with choices that you feel are less integral to getting Pastille End.
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