How do i make corner transitions for terrains line up properly?

I’m trying to make my own dirt path tiles to use in Tiled with the terrain feature and I’m finding it very difficult to align the corners. Is there any guidance on how to do this in Photoshop or Gimp so that we can be sure the alignment will match in Tiled? I’m finding myself spending hours going back and forth between Photoshop and Tiled using pure trial and error and it’s not really working.

I usually temporarily copy the tile I want to match to onto a second layer in gimp and then move it next to the other one and fix the transition there… That of course only works nicely if you only want to make changes to one of the tiles…

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