System administrators are paid to wake up at night to fix things.
Ask your boss, "do you want your users wait until the next morning for the system administrator to wake up and fix the issue? Or do you want the software inform the user how long it will take to fix the issue in seconds and start calling the system administrator to wake up and fix it?"
Because you answer based on your preferences as a worker who wants to avoid the extra work to make the system perfect and not your boss's preferences.
Ask your boss, "do you want your users wait until the next morning for the system administrator to wake up and fix the issue? Or do you want the software inform the user how long it will take to fix the issue in seconds and start calling the system administrator to wake up and fix it?"
Because you answer based on your preferences as a worker who wants to avoid the extra work to make the system perfect and not your boss's preferences.