I am currently on PFML medical leave in Massachusetts due to a serious health condition, which started in July and is expected to last until December when I will have used up my 20 weeks. Given my recovery, I am considering resigning when I return. I’ve heard that I might still qualify for unemployment benefits if I resign due to a serious health condition, but I want to confirm if that’s true. Additionally, I would like to offer my employer one to two weeks of remote work to help with the transition, as I genuinely appreciate my time there. However, I am concerned about whether returning briefly and then resigning two weeks later would affect my eligibility for unemployment benefits. I’m hoping to clarify these points before making any decisions.