In a password field, the system is in Secure Input Mode. In this mode, applications (quite rightly) cannot see your keyboard or typing. So Typed String triggers will not work. Also, in a password field, because Keyboard Maestro cannot see your keyboard, it cannot see what keys are pressed, so it cannot simulate a release keystroke if required. This happens for example if you had a hot key of Control-h, and typed “health” in to a password field. When Keyboard Maestro goes to type the “h”, it looks at the keyboard, but cannot see that the “h” is already pressed (from you holding the “h” key down), so it does not know it has to release the “h” key first. So it simulates a “h” press, which the system ignored, and then the “h” release, and carries on, resulting in a password of “ealth”.