It looks like this should be a simple case of turning on “keep sharp edges”, but that doesn’t do it.
What I’d like to do is: When I click a face to apply a face group, I want to apply that face group to the face and all connected planar faces. So for example if I have a cube, and I click one side, I only want to apply the face group to that side. If I have a cylinder and I click the top, I want to apply the face group only to the top.
Currently it seems I can only (1) click to apply the face group to the entire model, or (2) manually apply the face group to one face at a time.
Is there a way to apply a face group to a face and all connected planar faces?
That is what the brush is for and paint only front facing geometry.
Hi, could you possibly say a little more about this? Which brush are you referring to?
I believe he’s referring to the Front Facing Vertex Only option in the brush settings.
Just about every brush has this and is quite useful. It sounds like it may work for what you’re asking for.
That is definitely helpful, thank you!
It does paint ALL planar faces, not limited to ones that are contiguous with the first face. But it’s useful.
What would be ideal is a “planar flood fill” tool, ie: Click one face, and all contiguous planar faces are set to the same group. Maybe this is something that could be added one day! 
For flat edgy shapes you can set keep sharp edges filter…
But there is no flood fill / normal direction by tap
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