Any way to auto-overwrite when copying files?

Solution 1:

Open a powershell window and use its copy-item cmdlet with -recurse -force to overwrite. This would be a reasonable workaround.

Solution 2:

Use

xcopy <source> <destination> /S /E /Y

That should be sufficient.

Solution 3:

Yeah it's annoying. You could try Classic Shell, which will give you XP's copy/paste overwrite all y/n style.