If you enable Group search first, usersync starts with syncing groups and bringing in users belonging to those groups (of course with your filter settings). Most likely this new user did not have any groups (for your filter), so did not get sync'ed.
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Can you try adding groups to this user? Enable debug and see if there are any logs in usersync or admin logs. If possible, share the configs like ldap search filters and search base.
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If this is HA envrinonment, please follow steps mentioned here. https://community.hortonworks.com/articles/35019/oozie-ha-configuration-with-kerberos.html
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In the above situation, I believe 'user1' will be able to grant to 'user2' any permissions, because delegate admin access is for the resources specified, not for the specific permissions. @sneethiraj can offer more insights.
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If this is kerberos env, make sure there are no kerberos ticket renewal errors. Also, are you using SSL for ranger? In that case, make sure plugins are configured to trust ranger admin certificate.
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