Java 8 and prior versions have Java Web Start, which auto-updates the application when we change it. Oracle has recommended that users migrate to jlink, as that is the new Orac
Do you use maven?
I've resolved my similar problem with maven (I need to update an EAR).
My main app (the ear package) has a pom.xml with listed the dependencies and repositories.
The dependencies have the
tag with a range (documentation) as in this example
[1.0.0,)
That means : get version 1.0.0 or newer of the dependency. (You can put also an upper bound to the version, [1.0.0, 2.0.0) so if you develope a new version, it is not used in old app)
In the repository section I added my personal repository.
Now, in the remote machine I need only to rebuild my ear package with maven : the compiler download the newer version of my jar and put it together.
You need a system to check if there are newer dependencies version and warn the user to update the app and also lock its work (you can't work if you don't update). Maybe you need a little app to make users do the rebuild process easily. It's 1990's but a lot of desktop-app works in this way
PRO
CONTRO
You need to build the app in the remote machine, so the client must have a JDK and access to your repository (like artifactory);
You must write code in different jars and add them like dependencies in the main archive.
You must change JAR version each time and publish on the repository (this could be a good practice)