If you are in the midst of an upgrade like this, then you might want to program defensively. In this case I would do that by applying annotations like FindBugs'

If you are in the midst of an upgrade like this, then you might want to program defensively. In this case I would do that by applying annotations like FindBugs' @CheckForNull or @Nonnull or @Nullable. Across a trust boundary like an interface, it's possible to establish a convention like: every reference shall have one of those. You might be able to write a CheckStyle rule that verifies that every reference either has an annotation or is an Optional. Last but not least, assertions can be tremendously useful. Add Objects.requireNonNull() checks liberally, especially anywhere you pass a reference from one place to another without using it. By applying these techniques you can quickly create a "demilitarized zone" for null, allowing you to use Optional confidently on the other side. Errors are caught quickly and locally by analysis and assertions. In a large codebase it's not an all at once upgrade, unless you refactor checked by static analysis, but you can be confident in the parts you've upgraded.