Greetings all, I have been using ZBrush for over 11 years now but something has really been bugging for years. I’ve been trying to make a hollow pumpkin. I found that I can make it hollow by using extraction in the subtools. So far so good. I have hollow base and a cap. Now when I try to cut the eyes out using a prism shaped dynamesh subtool using dynamesh subtraction it doesn’t allow for it be cut all the way through, instead closing the hole. Apparently an object that is hollow shell can only have one hole. I’ve tried the technique of forming a separate polygroup through masking and when I delete the hidden topology I do not get a true hole. Any suggestions?
You could also just cut the holes in each side of the surface and then bridge polygons in between.
The Dynamesh Create Shell function seems exactly the tool for what you describe. Create your pumpkin shell, then cut out the face with Dynamesh inserts. See Pic. If the Dynamesh subtractions are failing to work as intended, and you’re certain you’ve eliminated the possibility of user error by being sure you’re able to perform negative subtractions with other tools reliably, then that is probably a separate issue.
There are always a half dozen ways to get from A to B in Zbrush if that doesn’t suit you. If you want to draw the cutouts more organically, you could duplicate your pumpkin inside itself as another subtool, scale the inner pumpkin down, push in your face on the outer pumpkin with alphas or brushes past the surface of the inner pumkin, then merge the two subtools, group the inner pumpkin as a negative dynamesh sub, and subtract the core pumpkin from the outer. The Slice Curve brush can be used in conjunction with the transpose extrude function to get razor crisp cuts. You can then use the wonderful Zremesher to derive some more manageable low poly wires so you can isolate poly loops for creasing:
You may also want to play around with storing a morph target of your pumpkin, masking a face on via brush, alpha, or polypaint, inflating, then using the “Create Difference Mesh” in the Tool > Morph menu. Again, Zremesher can be used to clean up geometry.
Im sure you can find other ways to get what you want as well.
[edit] You may want to consider posting a smaller pic in your thread to avoid blowing out the thread formatting. If I have to scroll on a 1080p monitor just to see what I’m typing, thats an awfully big pic 
!