This document discusses the complexities of developing practical web automation tools based on observations from user studies. It identifies challenges such as dealing with uncertainty due to the lack of standards in web technologies, maximizing user trust by ensuring user control and recoverability, and minimizing cognitive load. An example automation assistant is described that guides users step-by-step through tasks by suggesting actions and automating one action at a time with user confirmation. The conclusion notes some successes but that full automation has not been achieved due to uncertainties from lack of standardization, and that building trust and usability remain key challenges.