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Taking a stack composed of 30 web applications and their service dependencies to the cloud is no easy feat. Do you take the entirety of the stack or go the hybrid path? How transparent should the end result be to your technology teams? Does it look exactly the same in the cloud as it does in your data center? These are not rhetorical questions; they were very real for those tasked with the challenge of taking Edmunds.com to the AWS Cloud. This talk addresses these questions and many more, examining the challenges, successes, and lessons learned as the team took their first steps out of their own data centers. The presenters also cover how this experience is shaping the future direction of their stack's architecture to be friendlier to systems outside of their own data centers.