Most cloud providers now offer "easy to use" managed Kubernetes clusters, allowing us to get up and running in no time. Then our teams can just deploy containerized apps to them and life is good ..... Or is it? The truth is, this apparent simplicity fades quickly. The difficulties of adopting Kubernetes really hit hard on day two and beyond, when you need to integrate with existing infrastructure technologies and techniques. This includes IAM, networking, load balancing, DNS, monitoring, and logging, in addition to practices like continuous delivery, zero-downtime upgrades, and principle of least authority. Most of us underestimate how difficult these production concerns will be — even though it's getting easier by the day, it's still no casual walk in the park. In this talk, we'll discuss common challenges we see with end users and how we have approached addressing them. You will gain a broad awareness of these challenges so you know what to be on the lookout for and, by being proactive and going in with eyes wide open, will significantly increase the odds of success in your own team's journey to containers and Kubernetes.