We often talk about how to code, validate, and deploy database changes generally, according to a 'happy path' -- an imagined "normal" scenario in which events flow smoothly and teams follow best practices. But truthfully, few walk the happy path! In this session we will talk through three examples of real-world 'unhappy path' challenges, featuring changing timelines, tricky database patterns, and self-tuning databases. We'll talk through various options to overcome the challenges and give the pros and cons of each. You'll leave the session with new ideas and inspiration to build database DevOps workflows which help your team, even if you aren't on the 'happy path'.