If you do Pkg.update(), it should keep track of whether it updates any modules that were already imported into Main. If so, it should print a warning message telling the user that they will need to restart Julia if they want to use the updated modules.
Should be pretty easy to implement. (I would prefer that we don't print the warning unconditionally, e.g. if no imported modules were updated.)
See also #18150, cc @vtjnash.