The following a mix between an issue / feature request / documentation update request / support request. It depends on what’s intended.
The documentation to upgrade to a new version of Open edX recommends to use tutor local quickstart. If you have customized your docker images, it is asked to rebuild them before running quickstart.
It is not specified explicitely in the documentation about custom images, but you should probably run tutor config save before building the images. Otherwise env/build won’t be updated, and you will build images using templates for the previous Tutor version installed (last one that ran tutor config save), and depending on your configuration an old Open edX version + an old version of the customisations itself.
But, when tutor config save is run, it saves env/version. However, that file seems to be used in quickstart to determine if there is a need to make an upgrade (the equivalent to tutor local upgrade --from=...) and from which version.
So if you have custom images, you should run tutor local upgrade --from= after building images otherwise quickstart won’t do it for you, but the documentation doesn’t say that.
The documentation could be fixed, but we could also improve the upgrade detection logic to keep that documentation (and the upgrade process simple). Maybe we could find a way to detect which release is currently running by calling a command in the cms or lms service. It would also solve some issues if you’re overriding the Open edX version yourself, because this logic currently depends on the major version number of Tutor (although I’m not sure a major version of tutor can support multiple releases of Open edX). Also to ease things we could make this logic part of upgrade instead of just in quickstart so we don’t have to specify --from if we dont’ want to.