We will look at how the users, use cases and interest in cloud portability have changed over the past years as the cloud platform space has grown and consolidated while the types of available cloud services have diversified. We will examine challenges and potential pitfalls in exclusively targeting a single-vendor or "single-foundation" systems. We will discuss key motivations for working with a cross-cloud solution such as Apache jclouds even today, focussing not only on technical but also on experiential aspects such as understanding varied service types such as Chef or Docker in a consistent framework, and the ability to access a large pool of real-world experience in using multiple clouds.