I have tried digging through archived files and other bug reports but I just can't seem to figure out why the heck Autorank. I'm a little new to this server stuff so please cut me a little slack if it's obvious why it's not working. But whatever you need to know (.log files or anything) I will be happy to provide to help figure this problem out.

Can you show me the detailed error that shows up in your console? And don't worry, there are a lot of experienced server owners that have the same problems as you're having.

Here is the log file, the Autorank error is near the end/middle.

[09:38:14] [Server thread/INFO]: Starting minecraft server version 1.7.9
[09:38:14] [Server thread/INFO]: Loading properties
[09:38:14] [Server thread/INFO]: Default game type: SURVIVAL
[09:38:14] [Server thread/INFO]: Generating keypair
[09:38:14] [Server thread/INFO]: Starting Minecraft server on *:25565
[09:38:15] [Server thread/INFO]: This server is running CraftBukkit version git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks (MC: 1.7.9) (Implementing API version 1.7.9-R0.3-SNAPSHOT)
[09:38:15] [Server thread/INFO]: [Pl3xRecipes] Loading Pl3xRecipes v1.5
[09:38:15] [Server thread/INFO]: [bPermissions] Loading bPermissions v2.10.7
[09:38:15] [Server thread/INFO]: [WorldEdit] Loading WorldEdit v5.6.2
[09:38:15] [Server thread/INFO]: [LoyaltyPoints] Loading LoyaltyPoints v1.1.3
[09:38:15] [Server thread/INFO]: [Vault] Loading Vault v1.4.1-b436
[09:38:15] [Server thread/INFO]: [mcMMO] Loading mcMMO v1.5.00-b3547
[09:38:15] [Server thread/INFO]: [dynmap] Loading dynmap v1.9.4-991
[09:38:15] [Server thread/INFO]: [dynmap] Mod Support API available
[09:38:15] [Server thread/INFO]: [Essentials] Loading Essentials v2.13.1
[09:38:15] [Server thread/INFO]: [Jobs] Loading Jobs v2.11.4
[09:38:15] [Server thread/INFO]: [Autorank] Loading Autorank v3.1.1
[09:38:15] [Server thread/INFO]: [EssentialsProtect] Loading EssentialsProtect v2.13.1
[09:38:15] [Server thread/INFO]: [EssentialsSpawn] Loading EssentialsSpawn v2.13.1
[09:38:15] [Server thread/INFO]: [ChargeButton] Loading ChargeButton v1.0
[09:38:15] [Server thread/INFO]: [ChestShop] Loading ChestShop v3.7.9
[09:38:15] [Server thread/INFO]: [EssentialsChat] Loading EssentialsChat v2.13.1
[09:38:15] [Server thread/INFO]: [EssentialsAntiBuild] Loading EssentialsAntiBuild v2.13.1
[09:38:15] [Server thread/INFO]: [Vault] Enabling Vault v1.4.1-b436
[09:38:15] [Server thread/INFO]: [Vault] [Economy] Essentials Economy found: Waiting
[09:38:15] [Server thread/INFO]: [Vault][Permission] bPermissions2 hooked.
[09:38:15] [Server thread/INFO]: [Vault] [Permission] bPermissions 2 found: Loaded
[09:38:15] [Server thread/INFO]: [Vault] [Permission] SuperPermissions loaded as backup permission system.
[09:38:15] [Server thread/INFO]: [Vault][Chat] bPermissions2 hooked.
[09:38:15] [Server thread/INFO]: [Vault] [Chat] bPermssions2 found: Loaded
[09:38:15] [Server thread/INFO]: [Vault] Enabled Version 1.4.1-b436
[09:38:15] [Server thread/INFO]: [mcMMO] Enabling mcMMO v1.5.00-b3547
[09:38:18] [Thread-8/INFO]: ----- Bukkit Auto Updater -----
[09:38:18] [Thread-8/INFO]: It appears that you're running a Development Build, when you've specified in bukkit.yml that you prefer to run Recommended Builds.
[09:38:18] [Thread-8/INFO]: If you would like to be kept informed about new Development Build releases, it is recommended that you change 'preferred-channel' in your bukkit.yml to 'dev'.
[09:38:18] [Thread-8/INFO]: With that set, you will be told whenever a new version is available for download, so that you can always keep up to date and secure with the latest fixes.
[09:38:18] [Thread-8/INFO]: If you would like to disable this warning, simply set 'suggest-channels' to false in bukkit.yml.
[09:38:18] [Thread-8/INFO]: ----- ------------------- -----
[09:38:20] [Server thread/INFO]: Preparing level "world"
[09:38:20] [Server thread/INFO]: Preparing start region for level 0 (Seed: -4682106531336245128)
[09:38:21] [Server thread/INFO]: Preparing spawn area: 48%
[09:38:21] [Server thread/INFO]: Preparing start region for level 1 (Seed: -4682106531336245128)
[09:38:22] [Server thread/INFO]: Preparing spawn area: 50%
[09:38:23] [Server thread/INFO]: Preparing start region for level 2 (Seed: -4682106531336245128)
[09:38:23] [Server thread/INFO]: [Pl3xRecipes] Enabling Pl3xRecipes v1.5
[09:38:23] [Server thread/INFO]: �[0;36;22m[�[0;35;1mPl3xRecipes�[0;36;22m]�[m Pl3xRecipes v1.5 by BillyGalbreath enabled!�[m
[09:38:23] [Server thread/INFO]: [bPermissions] Enabling bPermissions v2.10.7
[09:38:23] [Server thread/INFO]: plugins\bPermissions\world
[09:38:23] [Server thread/INFO]: plugins\bPermissions\world_nether
[09:38:23] [Server thread/INFO]: plugins\bPermissions\world_the_end
[09:38:23] [Server thread/INFO]: plugins\bPermissions
[09:38:23] [Server thread/INFO]: [WorldEdit] Enabling WorldEdit v5.6.2
[09:38:23] [Server thread/INFO]: WEPIF: bPermissions detected! Using bPermissions for permissions
[09:38:24] [Server thread/INFO]: [LoyaltyPoints] Enabling LoyaltyPoints v1.1.3
[09:38:29] [Server thread/INFO]: [LoyaltyPoints] The plugin is up to date.
[09:38:29] [Server thread/INFO]: success
[09:38:29] [Server thread/INFO]: [LoyaltyPoints] Version 1.1.3 by Franzmedia is now enabled!
[09:38:29] [Server thread/INFO]: [dynmap] Enabling dynmap v1.9.4-991
[09:38:29] [Server thread/INFO]: [dynmap] Added 38 custom biome mappings
[09:38:29] [Server thread/INFO]: [dynmap] Using bPermissions 2.10.7 for access control
[09:38:29] [Server thread/INFO]: [dynmap] Mod Support processing completed
[09:38:30] [Server thread/INFO]: [dynmap] Loaded 22 shaders.
[09:38:30] [Server thread/INFO]: [dynmap] Loaded 82 perspectives.
[09:38:30] [Server thread/INFO]: [dynmap] Loaded 12 lightings.
[09:38:30] [Server thread/INFO]: [dynmap] Web server started on address 0.0.0.0:8123
[09:38:30] [Server thread/INFO]: [dynmap] version 1.9.4-991 is enabled - core version 1.9.4-1940
[09:38:30] [Server thread/INFO]: [dynmap] Loaded 3 maps of world 'world'.
[09:38:30] [Server thread/INFO]: [dynmap] Loaded 23 pending tile renders for world 'world'
[09:38:30] [Server thread/INFO]: [dynmap] Loaded 2 maps of world 'world_nether'.
[09:38:30] [Server thread/INFO]: [dynmap] Loaded 2 maps of world 'world_the_end'.
[09:38:30] [Server thread/INFO]: [dynmap] Enabled
[09:38:31] [Server thread/INFO]: [Essentials] Enabling Essentials v2.13.1
[09:38:31] [Server thread/INFO]: [Vault][Economy] Essentials Economy hooked.
[09:38:31] [Server thread/INFO]: Essentials: Using bPermissions2 based permissions.
[09:38:31] [Server thread/INFO]: [Jobs] Enabling Jobs v2.11.4
[09:38:31] [Jobs-DatabaseSaveTask/INFO]: [Jobs] Started database save task
[09:38:31] [Jobs-BufferedPaymentThread/INFO]: [Jobs] Started buffered payment thread
[09:38:31] [Server thread/INFO]: [Jobs] Plugin has been enabled succesfully.
[09:38:32] [Server thread/INFO]: [Autorank] Enabling Autorank v3.1.1
[09:38:32] [Server thread/INFO]: [Autorank] Simple config file loaded
[09:38:32] [Server thread/INFO]: [Autorank] Advanced config file loaded
[09:38:32] [Server thread/INFO]: [Autorank] Settings config file loaded
[09:38:32] [Server thread/INFO]: [Autorank] Starting to convert playerdata.yml
[09:38:32] [Server thread/INFO]: [Autorank] Playerdata file loaded. Keeping track of player progress!
[09:38:32] [Server thread/INFO]: [Autorank] Factions has not been found!
[09:38:32] [Server thread/INFO]: [Autorank] RoyalCommands has not been found!
[09:38:32] [Server thread/INFO]: [Autorank] Essentials has been found and can be used!
[09:38:32] [Server thread/INFO]: [Autorank] OnTime has not been found!
[09:38:32] [Server thread/INFO]: [Autorank] WorldGuard has not been found!
[09:38:32] [Server thread/INFO]: [Autorank] mcMMO has been found and can be used!
[09:38:32] [Server thread/INFO]: [Autorank] Stats has not been found!
[09:38:32] [Server thread/INFO]: [Autorank] Vault has been found and can be used!
[09:38:32] [Server thread/INFO]: [Autorank] No stats plugin found! Most requirements cannot be used!
[09:38:32] [Server thread/INFO]: [Autorank] Interval check every 5 minutes.
[09:38:32] [Server thread/INFO]: [Autorank] Data file loaded
[09:38:32] [Server thread/ERROR]: Error occurred while enabling Autorank v3.1.1 (Is it up to date?)
java.lang.ArrayIndexOutOfBoundsException: 1
at me.armar.plugins.autorank.playerchecker.builders.RankChangeBuilder.createFromSimpleConfig(RankChangeBuilder.java:55) ~[?:?]
at me.armar.plugins.autorank.playerchecker.PlayerChecker.initialiseFromConfigs(PlayerChecker.java:46) ~[?:?]
at me.armar.plugins.autorank.Autorank.onEnable(Autorank.java:203) ~[?:?]
at org.bukkit.plugin.java.JavaPlugin.setEnabled(JavaPlugin.java:316) ~[craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at org.bukkit.plugin.java.JavaPluginLoader.enablePlugin(JavaPluginLoader.java:324) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at org.bukkit.plugin.SimplePluginManager.enablePlugin(SimplePluginManager.java:404) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at org.bukkit.craftbukkit.v1_7_R3.CraftServer.loadPlugin(CraftServer.java:446) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at org.bukkit.craftbukkit.v1_7_R3.CraftServer.enablePlugins(CraftServer.java:380) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at net.minecraft.server.v1_7_R3.MinecraftServer.n(MinecraftServer.java:352) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at net.minecraft.server.v1_7_R3.MinecraftServer.g(MinecraftServer.java:326) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at net.minecraft.server.v1_7_R3.MinecraftServer.a(MinecraftServer.java:282) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at net.minecraft.server.v1_7_R3.DedicatedServer.init(DedicatedServer.java:182) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at net.minecraft.server.v1_7_R3.MinecraftServer.run(MinecraftServer.java:436) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
at net.minecraft.server.v1_7_R3.ThreadServerApplication.run(SourceFile:628) [craftbukkit.jar:git-Bukkit-1.7.9-R0.2-1-ga6e0bfd-b3095jnks]
[09:38:32] [Server thread/INFO]: [EssentialsProtect] Enabling EssentialsProtect v2.13.1
[09:38:32] [Server thread/INFO]: [EssentialsSpawn] Enabling EssentialsSpawn v2.13.1
[09:38:32] [Server thread/INFO]: [ChargeButton] Enabling ChargeButton v1.0
[09:38:32] [Server thread/INFO]: [ChargeButton] Enabled
[09:38:32] [Server thread/INFO]: [ChestShop] Enabling ChestShop v3.7.9
[09:38:32] [Server thread/INFO]: [ChestShop] Vault loaded! Found an economy plugin!
[09:38:35] [Server thread/INFO]: [EssentialsChat] Enabling EssentialsChat v2.13.1
[09:38:35] [Server thread/INFO]: [EssentialsAntiBuild] Enabling EssentialsAntiBuild v2.13.1
[09:38:35] [Server thread/INFO]: Server permissions file permissions.yml is empty, ignoring it
[09:38:36] [Server thread/INFO]: Done (16.773s)! For help, type "help" or "?"
[09:38:36] [Server thread/INFO]: [Jobs] [Jobs] Successfully linked with Vault.
[09:38:36] [pool-3-thread-8/INFO]: [Autorank] Converted playerdata.yml to UUID format
[09:38:36] [pool-3-thread-5/WARN]: [Autorank] Starting converting data.yml
[09:38:36] [pool-3-thread-5/WARN]: [Autorank] Conversion will take approx. ( guess for your data.yml)
[09:38:36] [pool-3-thread-5/INFO]: [Autorank] Converted data.yml to UUID format
[09:38:37] [Dynmap Render Thread/INFO]: [dynmap] Loading default resource pack
[09:38:38] [pool-3-thread-18/INFO]: [Vault] Checking for Updates:
[09:38:38] [pool-3-thread-18/INFO]: [Vault] No new version available
[09:45:21] [User Authenticator #1/INFO]: UUID of player Bensirpent07 is d57a381e-10c2-4767-94cd-e0a6352645f7
[09:45:24] [Server thread/INFO]: Bensirpent07[/192.168.1.3:49652] logged in with entity id 294 at ([world] 5.140682339109267, 63.0, 349.3328284731273)

Can I see your simple config file? It seems this error is reporting that there is something wrong with your SimpleConfig file.

Removed for format.

Could you provide a pastebin link? This is a bit unreadable ;)

You can go to pastebin.com and paste the link.

Yup, sorry about that, here you go
link-----> http://pastebin.com/hQEL5mC6

It might be because you have a permission group with a dash (-) in it. What happens if you remove the dash from the permission group? (I.e. rename it loneRanger)

Nope, taking the dash out still didn't work. Same message when I type /ar it just says "Autorank is disabled. Check your server.log!"

Still the same error? Can I see your settings config?

http://pastebin.com/162ZQdUy

Could you update to the latest dev build of Autorank?

If you still get the error, pastebin it here.

Same error... not sure what you wanted me to pastebin but... here is the settings config again. If that's what you want to see. http://pastebin.com/PB5JUj7z

No, I wanted to see the error again. Can you pastebin the output of that?

Omg, I've overlooked the problem the whole time... Look at the last line of your Simpleconfig. Can you spot what is missing? ;-)

Oh sorry... here you go http://pastebin.com/uNbwGRSr

Omg XD "kings guard" lol how did I miss that? lol... I poured over that for about 15 minutes... I swear the smallest things, I'm not on my laptop right now but when I get home I'll try it. So I'll let you know how it go's.

Well I fixed that and it's still not working -_-

What error is it giving?

This is an old error, as it says Autorank 3.1.1. You were still using the dev version, right?

http://pastebin.com/v3xc9dCr

Yes

Hmm, can you restart the server. Because this error cannot be from the dev version.