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The biggest pain point in all my migrations to the cloud are all database layer items. So the latest issue is the company we acquired runs MongoDB and in AWS it is docdb (which is there version of Mongo.) There is enough difference that makes a lift and shift difficult without changing things inside Mongo. Another issue I had a while back from Multi region SQL moving to Azure. Some odd quorum drive support issues inside Azure. I tend to think a large part of the stack is "manageable" to migrate but I always same some odd issue at the data layer. Second issue specific to AWS is on premises NAS moving to S3 = shit performance. So you end up in some weird EC2 + share. Just pay the money and get the cloud enabled NAS. You can't tech your way out of cheap S3 storage.

Some pain points on my mind: - Dealing with regulatory requirements. Especially in financial institutions. - Skills. You can have good engineers who manage your on-prem infrastructure, databases, security, etc. It doesn't mean that they are or will be able to configure your cloud. - Managing cloud costs. Some organizations plan infrastructure budgets in a way that is not compatible with the cloud... - Performance problems with some quite custom solutions. For example, we had some problems with Oracle and EBS disks. @Vivek Desai S3 example is also quite interesting.

We only recommend migration to cloud for cloud compatible services. We know one company who went to cloud doing lift-and-shift and they struggled hard to get enough money for the cloud provider.

As with most topics, it is about more than tech/IT only. Consider the impact that a move to the cloud can have on your processes (IT and business) and your organisation (org design, governance, skills etc.) together with the obvious tech impact. A great resource on this topic is the book “Cloud Strategy” by Gregor Hohpe: https://architectelevator.com/book/cloudstrategy/

Yes! This book is a must-read for every manager/ decision-maker working in the IT field.

@Vivek Desai, you might want to take a look at EFS https://aws.amazon.com/efs/ for your AWS NAS needs. We have good experience using it with NFS

oh this was a few years back