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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?

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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.