It absolutely is - getting that right is pretty much the most complex part of the launcher & build process. (This is partly because it doesn’t run very often, so there’s not very many chances to improve it.)
Last time it happened, if I remember correctly, people had problems for weeks (as the updates filtered in) due to a very long list of reasons the update could fail.
As your docker-compose stands now, you’re relying on either (1) the official postgres image recognizing and performing an upgrade or (2) do it manually.
While (1) would be nice in the case of a skipped upgrade & an upgrader that can’t skip that far - you could use the intermediate images! it’s great!
However, I don’t think the official postgres images will actually do that for you.