Just updated from 4.4.31 to 5.0.8 and my DynMap (3.0 beta 5) would not load. Had to revert back to 4.4.31.

[14:53:45] [Server thread/ERROR]: Error occurred while enabling dynmap v3.0-beta-5-218 (Is it up to date?) java.lang.NoClassDefFoundError: me/lucko/luckperms/api/LuckPermsApi at org.dynmap.bukkit.permissions.LuckPermsPermissions.create(LuckPermsPermissions.java:26) ~[?:?] at org.dynmap.bukkit.DynmapPlugin.onEnable(DynmapPlugin.java:848) ~[?:?] at org.bukkit.plugin.java.JavaPlugin.setEnabled(JavaPlugin.java:263) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.java.JavaPluginLoader.enablePlugin(JavaPluginLoader.java:338) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.SimplePluginManager.enablePlugin(SimplePluginManager.java:420) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.craftbukkit.v1_14_R1.CraftServer.enablePlugin(CraftServer.java:467) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.craftbukkit.v1_14_R1.CraftServer.enablePlugins(CraftServer.java:381) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.MinecraftServer.a(MinecraftServer.java:474) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.DedicatedServer.init(DedicatedServer.java:290) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.MinecraftServer.run(MinecraftServer.java:876) ~[patched_1.14.4.jar:git-Paper-230] at java.lang.Thread.run(Thread.java:835) [?:?] Caused by: java.lang.ClassNotFoundException: me.lucko.luckperms.api.LuckPermsApi at java.net.URLClassLoader.findClass(URLClassLoader.java:436) ~[?:?] at org.bukkit.plugin.java.PluginClassLoader.findClass(PluginClassLoader.java:139) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.java.PluginClassLoader.findClass(PluginClassLoader.java:85) ~[patched_1.14.4.jar:git-Paper-230] at java.lang.ClassLoader.loadClass(ClassLoader.java:588) ~[?:?] at java.lang.ClassLoader.loadClass(ClassLoader.java:521) ~[?:?] ... 11 more [14:53:45] [Server thread/INFO]: [dynmap] Disabling dynmap v3.0-beta-5-218 [14:53:45] [Server thread/ERROR]: Error occurred while disabling dynmap v3.0-beta-5-218 (Is it up to date?) java.lang.NullPointerException: null at org.dynmap.bukkit.DynmapPlugin.onDisable(DynmapPlugin.java:946) ~[?:?] at org.bukkit.plugin.java.JavaPlugin.setEnabled(JavaPlugin.java:265) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.java.JavaPluginLoader.disablePlugin(JavaPluginLoader.java:373) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.SimplePluginManager.disablePlugin(SimplePluginManager.java:453) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.java.JavaPluginLoader.enablePlugin(JavaPluginLoader.java:342) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.SimplePluginManager.enablePlugin(SimplePluginManager.java:420) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.craftbukkit.v1_14_R1.CraftServer.enablePlugin(CraftServer.java:467) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.craftbukkit.v1_14_R1.CraftServer.enablePlugins(CraftServer.java:381) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.MinecraftServer.a(MinecraftServer.java:474) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.DedicatedServer.init(DedicatedServer.java:290) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.MinecraftServer.run(MinecraftServer.java:876) ~[patched_1.14.4.jar:git-Paper-230] at java.lang.Thread.run(Thread.java:835) [?:?]

You probably need the legacy API extension:

https://github.com/lucko/LuckPerms/wiki/Extensions#extension-legacy-api

same here

It's unable to load the legacy API.

[17:52:44] [Server thread/ERROR]: Could not load 'plugins/extension-legacy-api-1.0.0.jar' in folder 'plugins' org.bukkit.plugin.InvalidDescriptionException: Invalid plugin.yml at org.bukkit.plugin.java.JavaPluginLoader.getPluginDescription(JavaPluginLoader.java:159) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.plugin.SimplePluginManager.loadPlugins(SimplePluginManager.java:142) ~[patched_1.14.4.jar:git-Paper-230] at org.bukkit.craftbukkit.v1_14_R1.CraftServer.loadPlugins(CraftServer.java:355) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.DedicatedServer.init(DedicatedServer.java:226) ~[patched_1.14.4.jar:git-Paper-230] at net.minecraft.server.v1_14_R1.MinecraftServer.run(MinecraftServer.java:876) ~[patched_1.14.4.jar:git-Paper-230] at java.lang.Thread.run(Thread.java:835) [?:?] Caused by: java.io.FileNotFoundException: Jar does not contain plugin.yml ... 6 more

If you scroll further up that page, it tells you where to correctly install the extensions - in a folder named extensions inside the LuckPerms folder.

Ha! For some reason I didn't scroll up.

After correctly installing the extension the issue has been resolved.

Thank you.

@illumeleet make sure to follow the above to fix this issue on your server too.