Friend unable to join my Paper 1.14.4 Server

My friend seems to be unable to join my server at times. I believe it tells him that he timed out. There are 3 of us and all of our connections are good so it doesn’t seem to be our internet. Here is part of the log. [21:11:52] [Server thread/INFO]: P1N34PPL3_K1NG lost connection: Disconnected
[21:11:52] [Server thread/INFO]: P1N34PPL3_K1NG left the game
[21:11:59] [User Authenticator #2/INFO]: UUID of player P1N34PPL3_K1NG is 05f4b334-4946-4439-835e-8f82cc752d25
[21:11:59] [Server thread/INFO]: P1N34PPL3_K1NG[/---------------] logged in with entity id 3005 at ([PersonalHardcore]355.49151590464965, 63.9375, 439.2917601053502)
[21:12:20] [Server thread/INFO]: P1N34PPL3_K1NG lost connection: Disconnected
[21:12:20] [Server thread/INFO]: P1N34PPL3_K1NG left the game

my other friend is able to freely join as he wants but for some reason P1N34PPL3_K1NG can’t.
The problem started appearing about a week ago when we were on 1.14.3 and the problem seems to have carried over.
I was able to temporarily fix the problem by restarting the server, making sure no one other than him joined (because if they did the problem would occur) and having him join.
Here is the full log

[21:07:25] [Server thread/INFO]: Starting minecraft server version 1.14.4
[21:07:25] [Server thread/INFO]: Loading properties
[21:07:25] [Server thread/INFO]: This server is running Paper version git-Paper-152 (MC: 1.14.4) (Implementing API version 1.14.4-R0.1-SNAPSHOT)
[21:07:25] [Server thread/INFO]: Debug logging is disabled
[21:07:25] [Server thread/INFO]: Server Ping Player Sample Count: 12
[21:07:25] [Server thread/INFO]: Using 4 threads for Netty based IO
[21:07:25] [Server thread/INFO]: Default game type: SURVIVAL
[21:07:25] [Server thread/INFO]: Generating keypair
[21:07:26] [Server thread/INFO]: Starting Minecraft server on *:25565
[21:07:26] [Server thread/INFO]: Using default channel type
[21:07:30] [Server thread/INFO]: [WorldEdit] Loading WorldEdit v7.0.0;214af8a
[21:07:31] [Server thread/INFO]: Got request to register class com.sk89q.worldedit.bukkit.BukkitServerInterface with WorldEdit [[email protected]]
[21:07:31] [Server thread/INFO]: [StaffPlus] Loading StaffPlus v3.2.9.3
[21:07:31] [Server thread/INFO]: Server permissions file permissions.yml is empty, ignoring it
[21:07:31] [Server thread/INFO]: [WorldEdit] Enabling WorldEdit v7.0.0;214af8a
[21:07:31] [Server thread/INFO]: WEPIF: Using the Bukkit Permissions API.
[21:07:31] [Server thread/INFO]: Preparing level “PersonalHardcore”
[21:07:31] [Server thread/INFO]: Reloading ResourceManager: Default, bukkit
[21:07:31] [Server thread/INFO]: Loaded 6 recipes
[21:07:32] [Server thread/INFO]: -------- World Settings For [PersonalHardcore] --------
[21:07:32] [Server thread/INFO]: View Distance: 20
[21:07:32] [Server thread/INFO]: Allow Zombie Pigmen to spawn from portal blocks: true
[21:07:32] [Server thread/INFO]: Item Merge Radius: 2.5
[21:07:32] [Server thread/INFO]: Item Despawn Rate: 6000
[21:07:32] [Server thread/INFO]: Arrow Despawn Rate: 1200
[21:07:32] [Server thread/INFO]: Nerfing mobs spawned from spawners: false
[21:07:32] [Server thread/INFO]: Zombie Aggressive Towards Villager: true
[21:07:32] [Server thread/INFO]: Custom Map Seeds: Village: 10387312 Desert: 14357617 Igloo: 14357618 Jungle: 14357619 Swamp: 14357620 Monument: 10387313Ocean: 14357621 Shipwreck: 165745295 Slime: 987234911
[21:07:32] [Server thread/INFO]: Hopper Transfer: 8 Hopper Check: 1 Hopper Amount: 1
[21:07:32] [Server thread/INFO]: Experience Merge Radius: 3.0
[21:07:32] [Server thread/INFO]: Cactus Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Cane Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Melon Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Mushroom Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Pumpkin Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Sapling Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Beetroot Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Carrot Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Potato Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Wheat Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: NetherWart Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Vine Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Cocoa Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Bamboo Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: SweetBerry Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Kelp Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Mob Spawn Range: 8
[21:07:32] [Server thread/INFO]: Entity Activation Range: An 32 / Mo 32 / Ra 48 / Mi 16 / Tiv true
[21:07:32] [Server thread/INFO]: Entity Tracking Range: Pl 48 / An 48 / Mo 48 / Mi 32 / Other 64
[21:07:32] [Server thread/INFO]: Tile Max Tick Time: 50ms Entity max Tick Time: 50ms
[21:07:32] [Server thread/INFO]: Max TNT Explosions: 100
[21:07:32] [Server thread/INFO]: Using com.sk89q.worldedit.bukkit.adapter.impl.Spigot_v1_14_R2 as the Bukkit adapter
[21:07:32] [Server thread/WARN]: Failed to load the built-in legacy id registry
java.lang.NoSuchMethodError: net.minecraft.server.v1_14_R1.IBlockState.d()Ljava/util/Collection;
at com.sk89q.worldedit.bukkit.adapter.impl.Spigot_v1_14_R2.getProperties(Spigot_v1_14_R2.java:398) ~[?:?]
at com.sk89q.worldedit.bukkit.BukkitBlockRegistry.getProperties(BukkitBlockRegistry.java:52) ~[?:?]
at com.sk89q.worldedit.world.block.BlockType.lambda$getPropertyMap$1(BlockType.java:121) ~[?:?]
at com.sk89q.worldedit.world.block.BlockType.updateField(BlockType.java:74) ~[?:?]
at com.sk89q.worldedit.world.block.BlockType.getPropertyMap(BlockType.java:120) ~[?:?]
at com.sk89q.worldedit.extension.factory.parser.DefaultBlockParser.parseProperties(DefaultBlockParser.java:171) ~[?:?]
at com.sk89q.worldedit.extension.factory.parser.DefaultBlockParser.parseLogic(DefaultBlockParser.java:314) ~[?:?]
at com.sk89q.worldedit.extension.factory.parser.DefaultBlockParser.parseFromInput(DefaultBlockParser.java:88) ~[?:?]
at com.sk89q.worldedit.extension.factory.parser.DefaultBlockParser.parseFromInput(DefaultBlockParser.java:61) ~[?:?]
at com.sk89q.worldedit.internal.registry.AbstractFactory.parseFromInput(AbstractFactory.java:73) ~[?:?]
at com.sk89q.worldedit.world.registry.LegacyMapper.loadFromResource(LegacyMapper.java:99) ~[?:?]
at com.sk89q.worldedit.world.registry.LegacyMapper.(LegacyMapper.java:66) ~[?:?]
at com.sk89q.worldedit.world.registry.LegacyMapper.getInstance(LegacyMapper.java:179) ~[?:?]
at com.sk89q.worldedit.WorldEdit.loadMappings(WorldEdit.java:367) ~[?:?]
at com.sk89q.worldedit.bukkit.WorldEditPlugin.setupWorldData(WorldEditPlugin.java:153) ~[?:?]
at com.sk89q.worldedit.bukkit.WorldEditPlugin.access$100(WorldEditPlugin.java:89) ~[?:?]
at com.sk89q.worldedit.bukkit.WorldEditPlugin$WorldInitListener.onWorldInit(WorldEditPlugin.java:466) ~[?:?]
at com.destroystokyo.paper.event.executor.MethodHandleEventExecutor.execute(MethodHandleEventExecutor.java:37) ~[patched_1.14.4.jar:git-Paper-152]
at co.aikar.timings.TimedEventExecutor.execute(TimedEventExecutor.java:80) ~[patched_1.14.4.jar:git-Paper-152]
at org.bukkit.plugin.RegisteredListener.callEvent(RegisteredListener.java:70) ~[patched_1.14.4.jar:git-Paper-152]
at org.bukkit.plugin.SimplePluginManager.callEvent(SimplePluginManager.java:545) ~[patched_1.14.4.jar:git-Paper-152]
at net.minecraft.server.v1_14_R1.MinecraftServer.a(MinecraftServer.java:445) ~[patched_1.14.4.jar:git-Paper-152]
at net.minecraft.server.v1_14_R1.DedicatedServer.init(DedicatedServer.java:282) ~[patched_1.14.4.jar:git-Paper-152]
at net.minecraft.server.v1_14_R1.MinecraftServer.run(MinecraftServer.java:869) ~[patched_1.14.4.jar:git-Paper-152]
at java.lang.Thread.run(Unknown Source) [?:1.8.0_221]
[21:07:32] [Server thread/INFO]: Registering commands with com.sk89q.worldedit.bukkit.BukkitServerInterface
[21:07:32] [Server thread/INFO]: -------- World Settings For [PersonalHardcore_nether] --------
[21:07:32] [Server thread/INFO]: View Distance: 20
[21:07:32] [Server thread/INFO]: Allow Zombie Pigmen to spawn from portal blocks: true
[21:07:32] [Server thread/INFO]: Item Merge Radius: 2.5
[21:07:32] [Server thread/INFO]: Item Despawn Rate: 6000
[21:07:32] [Server thread/INFO]: Arrow Despawn Rate: 1200
[21:07:32] [Server thread/INFO]: Nerfing mobs spawned from spawners: false
[21:07:32] [Server thread/INFO]: Zombie Aggressive Towards Villager: true
[21:07:32] [Server thread/INFO]: Custom Map Seeds: Village: 10387312 Desert: 14357617 Igloo: 14357618 Jungle: 14357619 Swamp: 14357620 Monument: 10387313Ocean: 14357621 Shipwreck: 165745295 Slime: 987234911
[21:07:32] [Server thread/INFO]: Hopper Transfer: 8 Hopper Check: 1 Hopper Amount: 1
[21:07:32] [Server thread/INFO]: Experience Merge Radius: 3.0
[21:07:32] [Server thread/INFO]: Cactus Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Cane Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Melon Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Mushroom Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Pumpkin Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Sapling Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Beetroot Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Carrot Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Potato Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Wheat Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: NetherWart Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Vine Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Cocoa Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Bamboo Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: SweetBerry Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Kelp Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Mob Spawn Range: 8
[21:07:32] [Server thread/INFO]: Entity Activation Range: An 32 / Mo 32 / Ra 48 / Mi 16 / Tiv true
[21:07:32] [Server thread/INFO]: Entity Tracking Range: Pl 48 / An 48 / Mo 48 / Mi 32 / Other 64
[21:07:32] [Server thread/INFO]: Tile Max Tick Time: 50ms Entity max Tick Time: 50ms
[21:07:32] [Server thread/INFO]: Max TNT Explosions: 100
[21:07:32] [Server thread/INFO]: -------- World Settings For [PersonalHardcore_the_end] --------
[21:07:32] [Server thread/INFO]: View Distance: 20
[21:07:32] [Server thread/INFO]: Allow Zombie Pigmen to spawn from portal blocks: true
[21:07:32] [Server thread/INFO]: Item Merge Radius: 2.5
[21:07:32] [Server thread/INFO]: Item Despawn Rate: 6000
[21:07:32] [Server thread/INFO]: Arrow Despawn Rate: 1200
[21:07:32] [Server thread/INFO]: Nerfing mobs spawned from spawners: false
[21:07:32] [Server thread/INFO]: Zombie Aggressive Towards Villager: true
[21:07:32] [Server thread/INFO]: Custom Map Seeds: Village: 10387312 Desert: 14357617 Igloo: 14357618 Jungle: 14357619 Swamp: 14357620 Monument: 10387313Ocean: 14357621 Shipwreck: 165745295 Slime: 987234911
[21:07:32] [Server thread/INFO]: Hopper Transfer: 8 Hopper Check: 1 Hopper Amount: 1
[21:07:32] [Server thread/INFO]: Experience Merge Radius: 3.0
[21:07:32] [Server thread/INFO]: Cactus Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Cane Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Melon Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Mushroom Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Pumpkin Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Sapling Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Beetroot Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Carrot Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Potato Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Wheat Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: NetherWart Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Vine Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Cocoa Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Bamboo Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: SweetBerry Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Kelp Growth Modifier: 100%
[21:07:32] [Server thread/INFO]: Mob Spawn Range: 8
[21:07:32] [Server thread/INFO]: Entity Activation Range: An 32 / Mo 32 / Ra 48 / Mi 16 / Tiv true
[21:07:32] [Server thread/INFO]: Entity Tracking Range: Pl 48 / An 48 / Mo 48 / Mi 32 / Other 64
[21:07:32] [Server thread/INFO]: Tile Max Tick Time: 50ms Entity max Tick Time: 50ms
[21:07:32] [Server thread/INFO]: Max TNT Explosions: 100
[21:07:32] [Server thread/INFO]: Preparing start region for dimension ‘PersonalHardcore’/minecraft:overworld
[21:07:33] [Server thread/INFO]: Preparing spawn area: 0%
[21:07:33] [Server thread/INFO]: Preparing spawn area: 0%
[21:07:33] [Server thread/INFO]: Loaded 441 spawn chunks for world PersonalHardcore
[21:07:33] [Server thread/INFO]: Time elapsed: 946 ms
[21:07:33] [Server thread/INFO]: Preparing start region for dimension ‘PersonalHardcore_nether’/minecraft:the_nether
[21:07:33] [Server thread/INFO]: Preparing spawn area: 0%
[21:07:33] [Server thread/INFO]: Loaded 441 spawn chunks for world PersonalHardcore_nether
[21:07:33] [Server thread/INFO]: Time elapsed: 477 ms
[21:07:33] [Server thread/INFO]: Preparing start region for dimension ‘PersonalHardcore_the_end’/minecraft:the_end
[21:07:34] [Server thread/INFO]: Preparing spawn area: 0%
[21:07:34] [Server-Worker-2/INFO]: Preparing spawn area: 100%
[21:07:34] [Server thread/INFO]: Loaded 441 spawn chunks for world PersonalHardcore_the_end
[21:07:34] [Server thread/INFO]: Time elapsed: 681 ms
[21:07:34] [Server thread/INFO]: [StaffPlus] Enabling StaffPlus v3.2.9.3
[21:07:34] [Server thread/INFO]: [APIManager] API class ‘org.inventivetalent.packetlistener.PacketListenerAPI’ is not yet initialized. Creating new instance.
[21:07:34] [Server thread/INFO]: [ReflectionHelper] I am loaded from package org.inventivetalent.packetlistener.reflection.minecraft
[21:07:34] [Server thread/INFO]: [ReflectionHelper] Version is v1_14_R1 (11401)
[21:07:34] [Server thread/INFO]: [PacketListenerAPI] Using INChannel
[21:07:34] [Server thread/INFO]: [PacketListenerAPI] Injected custom channel handlers.
[21:07:34] [Server thread/INFO]: [PacketListenerAPI] Adding channels for online players…
[21:07:34] [Server thread/INFO]: [Staff+] Version protocol set to ‘v1_14_R1’.
[21:07:34] [Server thread/INFO]: [Staff+] Staff+ has been enabled! Initialization took 95ms.
[21:07:34] [Server thread/INFO]: [Staff+] Plugin created by Shortninja.
[21:07:34] [Server thread/INFO]: Done (3.331s)! For help, type “help”
[21:07:34] [Server thread/INFO]: Timings Reset
[21:08:05] [User Authenticator #1/INFO]: UUID of player P1N34PPL3_K1NG is 05f4b334-4946-4439-835e-8f82cc752d25
[21:08:05] [Server thread/INFO]: P1N34PPL3_K1NG[-----------] logged in with entity id 220 at ([PersonalHardcore]362.5, 57.0625002, 387.5)
[21:08:14] [User Authenticator #1/INFO]: UUID of player m_l_alexander is f054fa3f-47bf-49b0-b674-9ee90c9d57a4
[21:08:14] [Server thread/INFO]: m_l_alexander[/----------] logged in with entity id 1035 at ([PersonalHardcore]2824.699999988079, 72.0, 341.0141534687617)
[21:08:17] [Server thread/INFO]: m_l_alexander issued server command: /op P1N34PPL3_K1NG
[21:08:17] [Server thread/INFO]: [m_l_alexander: Made P1N34PPL3_K1NG a server operator]
[21:08:22] [User Authenticator #1/INFO]: UUID of player dwarfman03 is 8208d022-e38c-44dd-b065-be6ff1240f5b
[21:08:23] [Server thread/INFO]: dwarfman03[----------] logged in with entity id 1368 at ([PersonalHardcore]374.23356351921996, 70.9951193662697, 336.0164194102823)
[21:08:50] [Server thread/INFO]: m_l_alexander issued server command: /op dwarfman03
[21:08:50] [Server thread/INFO]: [m_l_alexander: Made dwarfman03 a server operator]
[21:09:03] [Server thread/INFO]: dwarfman03 issued server command: /gamemode su
[21:09:10] [Server thread/INFO]: dwarfman03 issued server command: /gamemode survival
[21:09:10] [Server thread/INFO]: [dwarfman03: Set own game mode to Survival Mode]
[21:11:52] [Server thread/INFO]: P1N34PPL3_K1NG lost connection: Disconnected
[21:11:52] [Server thread/INFO]: P1N34PPL3_K1NG left the game
[21:11:59] [User Authenticator #2/INFO]: UUID of player P1N34PPL3_K1NG is 05f4b334-4946-4439-835e-8f82cc752d25
[21:11:59] [Server thread/INFO]: P1N34PPL3_K1NG[/---------] logged in with entity id 3005 at ([PersonalHardcore]355.49151590464965, 63.9375, 439.2917601053502)
[21:12:20] [Server thread/INFO]: P1N34PPL3_K1NG lost connection: Disconnected
[21:12:20] [Server thread/INFO]: P1N34PPL3_K1NG left the game
[21:12:21] [Server thread/INFO]: m_l_alexander lost connection: Disconnected
[21:12:21] [Server thread/INFO]: m_l_alexander left the game
[21:12:25] [Server thread/INFO]: dwarfman03 lost connection: Disconnected
[21:12:25] [Server thread/INFO]: dwarfman03 left the game
[21:12:38] [User Authenticator #2/INFO]: UUID of player P1N34PPL3_K1NG is 05f4b334-4946-4439-835e-8f82cc752d25
[21:12:38] [Server thread/INFO]: P1N34PPL3_K1NG[/-----------] logged in with entity id 3183 at ([PersonalHardcore]355.49151590464965, 63.9375, 439.2917601053502)
[21:12:48] [Server thread/INFO]: Stopping the server
[21:12:48] [Server thread/INFO]: Stopping server
[21:12:48] [Server thread/INFO]: [StaffPlus] Disabling StaffPlus v3.2.9.3
[21:12:48] [Server thread/INFO]: [Staff+] Staff+ is now disabling!
[21:12:48] [Server thread/INFO]: [PacketListenerAPI] Removing channels for online players…
[21:12:48] [Server thread/INFO]: [PacketListenerAPI] Removing packet handlers (1)…
[21:12:48] [Server thread/INFO]: [WorldEdit] Disabling WorldEdit v7.0.0;214af8a
[21:12:48] [Server thread/INFO]: Unregistering com.sk89q.worldedit.bukkit.BukkitServerInterface from WorldEdit
[21:12:48] [Server thread/INFO]: Saving players
[21:12:48] [Server thread/INFO]: P1N34PPL3_K1NG lost connection: Server closed
[21:12:48] [Server thread/INFO]: P1N34PPL3_K1NG left the game
[21:12:48] [Server thread/INFO]: Saving worlds
[21:12:48] [Server thread/INFO]: Saving chunks for level ‘PersonalHardcore’/minecraft:overworld
[21:12:49] [Server thread/INFO]: ThreadedAnvilChunkStorage (PersonalHardcore): All chunks are saved
[21:12:49] [Server thread/INFO]: Saving chunks for level ‘PersonalHardcore_nether’/minecraft:the_nether
[21:12:50] [Server thread/INFO]: ThreadedAnvilChunkStorage (DIM-1): All chunks are saved
[21:12:50] [Server thread/INFO]: Saving chunks for level ‘PersonalHardcore_the_end’/minecraft:the_end
[21:12:50] [Server thread/INFO]: ThreadedAnvilChunkStorage (DIM1): All chunks are saved
[21:12:50] [Server thread/INFO]: ThreadedAnvilChunkStorage (PersonalHardcore): All chunks are saved
[21:12:50] [Server thread/INFO]: ThreadedAnvilChunkStorage (DIM-1): All chunks are saved
[21:12:50] [Server thread/INFO]: ThreadedAnvilChunkStorage (DIM1): All chunks are saved