System Information
Operating system: Windows-7-6.1.7601-SP1 64 Bits
Graphics card: GeForce GTX 660 Ti/PCIe/SSE2 NVIDIA Corporation 4.5.0 NVIDIA 442.59

Blender Version
Broken: version: 2.83 (sub 15), branch: master, commit date: 2020-04-23 21:07, hash: rBd712f1f83af8
Worked: (newest version of Blender that worked as expected)

Short description of error
Changes in brush settings undoed with brush stroke, made after settings.
It is always reproducible for weight paint and partially reproducible for sculpt mode.

Exact steps for others to reproduce the error

Weight paint

1. Enter WP mode
2. Change brush settings (weight /radius…)
3. Make a stroke
4. Ctrl+Z once — all settings back to previous state

Sculpt

1. Make sculpt template file with area, that starts right from sculpt mode.
2. Create new file with it (or use attached)
3. Change brush settings
4. Make stroke
5. Ctrl+Z once — brush settings back too