In the 21st century it is almost a precept that tax, like many other aspects of our financial world, would be substantially digital in nature. Currencies are becoming digital. Securities trading and banking are effectively already digital. Our daily lives are increasingly digital. Yet, there are aspects of financial services where it has proven extremely challenging to move out of a paper environment. In this article, the author uses practical examples to explain these challenges and offers insights into how and when the tax industry may catch up.