I was recently asked to investigate whether my team should switch from running our own ELK stack to paying for a SaaS logging vendor. Eventually, I concluded that we should switch, and so we did - but not without encountering significant pushback and unexpected difficulties along the way. In this talk, I'll explain the criteria we started out with for switching, what we did during the evaluation period, and what I wish we had done instead. We'll cover actionable lessons such as how to evaluate security, the right way to ask for feedback, and what you might not have thought to ask about in a vendor trial.