When D2L first moved to the cloud, we were concerned about being locked-in to one cloud provider. We were compelled to explore the opportunities of the cloud, so we overcame our perceived risk, and turned it into an opportunity by self-rolling tools and avoiding AWS native services. In this session, you learn how D2L tried to bypass the lock but eventually embraced it and opened the cage. Avoiding AWS native tooling and pure lifts of enterprise architecture caused a drastic inflation of costs. Learn how we shifted away from a self-rolled 'lift' into an efficient and effective 'shift' while prioritizing cost, client safety, AND speed of development. Learn from D2L's successes and missteps, and convert your own enterprise systems into the cloud both through native cloud births and enterprise conversions. This session discusses D2L’s use of Amazon EC2 (with a guest appearance by Reserved Instances), Elastic Load Balancing, Amazon EBS, Amazon DynamoDB, Amazon S3, AWS CloudFormation, AWS CloudTrail, Amazon CloudFront, AWS Marketplace, Amazon Route 53, AWS Elastic Beanstalk, and Amazon ElastiCache.