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For AssertJ 4, we wanted to upgrade to Java 17. However, we are discussing whether to stay on 8 or upgrade to 11. The main reason is to keep our effort reasonable and continue supporting users who cannot upgrade yet (e.g., RHEL 7 users under ELS). Any strong reason to keep upgrading to Java 17?

IMO the number of tails isn't important, assuming CI is automated. It's more important to reduce the number of backported changes. If a library would only fix security issues (like CVEs for itself and its dependencies), that should be very small. Not sure if I ever saw a secur. fix for AssertJ yet.