[19:23:37 ERROR]: Error occurred while enabling ChunkyBorder v1.1.50 (Is it up to date?)
com.google.gson.JsonSyntaxException: java.io.EOFException: End of input at line 10 column 5 path $.
at com.google.gson.Gson.fromJson(Gson.java:1224) ~[gson-2.10.jar:?]
at com.google.gson.Gson.fromJson(Gson.java:1124) ~[gson-2.10.jar:?]
at com.google.gson.Gson.fromJson(Gson.java:1094) ~[gson-2.10.jar:?]
at org.popcraft.chunkyborder.ChunkyBorder.loadBorders(ChunkyBorder.java:230) ~[ChunkyBorder-1.1.50.jar:?]
at org.popcraft.chunkyborder.ChunkyBorder.(ChunkyBorder.java:60) ~[ChunkyBorder-1.1.50.jar:?]
at org.popcraft.chunkyborder.ChunkyBorderBukkit.onEnable(ChunkyBorderBukkit.java:78) ~[ChunkyBorder-1.1.50.jar:?]
at org.bukkit.plugin.java.JavaPlugin.setEnabled(JavaPlugin.java:281) ~[paper-api-1.19.4-R0.1-SNAPSHOT.jar:?]
at io.papermc.paper.plugin.manager.PaperPluginInstanceManager.enablePlugin(PaperPluginInstanceManager.java:189) ~[paper-1.19.4.jar:git-Paper-550]
at io.papermc.paper.plugin.manager.PaperPluginManagerImpl.enablePlugin(PaperPluginManagerImpl.java:104) ~[paper-1.19.4.jar:git-Paper-550]
at org.bukkit.plugin.SimplePluginManager.enablePlugin(SimplePluginManager.java:507) ~[paper-api-1.19.4-R0.1-SNAPSHOT.jar:?]
at org.bukkit.craftbukkit.v1_19_R3.CraftServer.enablePlugin(CraftServer.java:563) ~[paper-1.19.4.jar:git-Paper-550]
at org.bukkit.craftbukkit.v1_19_R3.CraftServer.enablePlugins(CraftServer.java:474) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.loadWorld0(MinecraftServer.java:638) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.loadLevel(MinecraftServer.java:437) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.dedicated.DedicatedServer.initServer(DedicatedServer.java:308) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.runServer(MinecraftServer.java:1104) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.lambda$spin$0(MinecraftServer.java:320) ~[paper-1.19.4.jar:git-Paper-550]
at java.lang.Thread.run(Thread.java:833) ~[?:?]
Caused by: java.io.EOFException: End of input at line 10 column 5 path $.
at com.google.gson.stream.JsonReader.nextNonWhitespace(JsonReader.java:1455) ~[gson-2.10.jar:?]
at com.google.gson.stream.JsonReader.doPeek(JsonReader.java:503) ~[gson-2.10.jar:?]
at com.google.gson.stream.JsonReader.hasNext(JsonReader.java:422) ~[gson-2.10.jar:?]
at com.google.gson.internal.bind.MapTypeAdapterFactory$Adapter.read(MapTypeAdapterFactory.java:183) ~[gson-2.10.jar:?]
at com.google.gson.internal.bind.MapTypeAdapterFactory$Adapter.read(MapTypeAdapterFactory.java:144) ~[gson-2.10.jar:?]
at com.google.gson.Gson.fromJson(Gson.java:1214) ~[gson-2.10.jar:?]
... 17 more
[19:23:37 INFO]: [ChunkyBorder] Disabling ChunkyBorder v1.1.50
[19:23:37 ERROR]: Error occurred (in the plugin loader) while disabling ChunkyBorder v1.1.50 (Is it up to date?)
java.lang.NullPointerException: Cannot invoke "org.popcraft.chunkyborder.ChunkyBorder.disable()" because "this.chunkyBorder" is null
at org.popcraft.chunkyborder.ChunkyBorderBukkit.onDisable(ChunkyBorderBukkit.java:215) ~[ChunkyBorder-1.1.50.jar:?]
at org.bukkit.plugin.java.JavaPlugin.setEnabled(JavaPlugin.java:283) ~[paper-api-1.19.4-R0.1-SNAPSHOT.jar:?]
at io.papermc.paper.plugin.manager.PaperPluginInstanceManager.disablePlugin(PaperPluginInstanceManager.java:224) ~[paper-1.19.4.jar:git-Paper-550]
at io.papermc.paper.plugin.manager.PaperPluginManagerImpl.disablePlugin(PaperPluginManagerImpl.java:109) ~[paper-1.19.4.jar:git-Paper-550]
at org.bukkit.plugin.SimplePluginManager.disablePlugin(SimplePluginManager.java:537) ~[paper-api-1.19.4-R0.1-SNAPSHOT.jar:?]
at io.papermc.paper.plugin.manager.PaperPluginInstanceManager.enablePlugin(PaperPluginInstanceManager.java:193) ~[paper-1.19.4.jar:git-Paper-550]
at io.papermc.paper.plugin.manager.PaperPluginManagerImpl.enablePlugin(PaperPluginManagerImpl.java:104) ~[paper-1.19.4.jar:git-Paper-550]
at org.bukkit.plugin.SimplePluginManager.enablePlugin(SimplePluginManager.java:507) ~[paper-api-1.19.4-R0.1-SNAPSHOT.jar:?]
at org.bukkit.craftbukkit.v1_19_R3.CraftServer.enablePlugin(CraftServer.java:563) ~[paper-1.19.4.jar:git-Paper-550]
at org.bukkit.craftbukkit.v1_19_R3.CraftServer.enablePlugins(CraftServer.java:474) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.loadWorld0(MinecraftServer.java:638) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.loadLevel(MinecraftServer.java:437) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.dedicated.DedicatedServer.initServer(DedicatedServer.java:308) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.runServer(MinecraftServer.java:1104) ~[paper-1.19.4.jar:git-Paper-550]
at net.minecraft.server.MinecraftServer.lambda$spin$0(MinecraftServer.java:320) ~[paper-1.19.4.jar:git-Paper-550]
at java.lang.Thread.run(Thread.java:833) ~[?:?]

This isn't a bug, you have a broken borders.json file. Most likely you edited it yourself incorrectly, or copied incorrectly, etc. I recommend deleting the file and re-setting the borders using the provided commands.