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the way how ACP transfers the users and responsibilities is completely based on iSetup + FNDLOAD functionality (this is the underlying tool used). FNDLOAD uses ldt files (data) and lct files (control). If you dive into the lct you will discover the cause why updates are sometimes taken and sometimes not.
What I have discovered is that an update made the same day will not be routed forward, but a change made a day later will be transferred.
This is a general behavior how the lct calls (pl/sql) have been implemented, so it might happen that this issue comes also up in other object types.
If we would run the FNDLOAD manually and if we would use the parameter FORCE, then all our changes will taken care as expected. In default, iSetup has defined the command, and does not use FORCE. Therefore your issue comes right up here.
The only solution I have in mind is changing (overwriting) the iSetup definition for FNDLOAD in the target environment. But this is not recommended and not easy to maintain.
Raise an SR and ask for help. Perhaps support has some ideas.