Cover Letter Helper

Applying to jobs means meeting the same upload field over and over. My old flow was: draft the letter, export a PDF, dig it out of the downloads folder, drag it into the form. Do that a few dozen times a week and your downloads folder becomes a graveyard of one-time PDFs.

The goal was to cut the file out of the loop: write the letter, click once, and the PDF lands in the application's upload field without ever touching disk.

It had to be a Chrome extension, because the problem lives inside other sites' pages and only a content script can reach their file inputs. The PDF is generated client-side in the popup, with a live preview before attaching. No server, nothing to host, and the letter text never leaves the browser.

The architecture splits cleanly under Manifest V3: the popup owns PDF generation and preview, the content script owns finding the right file input on the page and injecting the generated file. That split also made testing manageable, since I built dedicated demo and debug HTML pages that imitate upload forms, so I could test injection without opening a live job application.

The messy part is that every applicant tracking system renders upload fields differently. Standard file inputs work; some custom drag-and-drop widgets still need a manual fallback. That tradeoff felt fine: cover the common case end to end rather than chase every ATS variant.