For web scraping and task automation purposes, programmers write scripts to interact with websites. This is similar to writing end-to-end user interface (UI) test automation suites for software, but on third-party websites that the programmer does not own, introducing new challenges. A programmer might know what semantic operations they want their script to perform, but translating this to code can be difficult. The programmer must investigate the website’s internal structure, content, and how UI elements behave, and then write code to click, type, and otherwise interact with UI elements. Many tools and frameworks for creating web automation scripts exist but the challenges programmers face in using them remains understudied. We conducted two studies to study how programmers write web automation scripts. The first study focuses on understanding general challenges. The second focuses on the ways website UI context and script feedback can be helpful. We also provide a set of design findings that detail the kinds of context and feedback developers need while writing web automation scripts.