Snapping vertex groups to separate meshes for animation?

I have 3 meshes in blender, 1 is a mask, the other is the character it goes on, the 3rd is a separate piece that needs to be separate from the others but the mask needs to connect to both the character and the separate mesh via separate vertex groups.

Surface deform worked in the past, but now after a lot of fine tuning and cleanup it just doesn’t work anymore and the mask just moves off into the distance, I’ve tried cleaning everything up more just in case, but to no avail, I’m not even getting errors.

When the characters face moves I need the masks vertex group to move with those from the face, and the 3rd mesh to be the same but its a hard surface that moves.
What are my options?

Please and Thank You.

Hi, it’s really hard to understand from the description alone what is going on. Could you maybe share some screenshots and maybe the .blend file so it’s easier for the people who might be willing to help?

Thanks for replying, but I solved the problem.
And while I normally wouldn’t mind showing the blend file to get help, the character is not something I’m ready to show anyone yet.