diff --git a/src/main/java/net/knarcraft/paidsigns/PaidSigns.java b/src/main/java/net/knarcraft/paidsigns/PaidSigns.java
index 807933c..270a851 100644
--- a/src/main/java/net/knarcraft/paidsigns/PaidSigns.java
+++ b/src/main/java/net/knarcraft/paidsigns/PaidSigns.java
@@ -1,6 +1,8 @@
 package net.knarcraft.paidsigns;
 
 import net.knarcraft.paidsigns.command.AddCommand;
+import net.knarcraft.paidsigns.command.AddConditionCommand;
+import net.knarcraft.paidsigns.command.AddConditionTabCompleter;
 import net.knarcraft.paidsigns.command.AddTabCompleter;
 import net.knarcraft.paidsigns.command.ReloadTabCommand;
 import net.knarcraft.paidsigns.command.RemoveTabCommand;
@@ -105,6 +107,12 @@ public final class PaidSigns extends JavaPlugin {
             addCommand.setTabCompleter(new AddTabCompleter());
         }
 
+        PluginCommand addConditionCommand = this.getCommand("addPaidSignCondition");
+        if (addConditionCommand != null) {
+            addConditionCommand.setExecutor(new AddConditionCommand());
+            addConditionCommand.setTabCompleter(new AddConditionTabCompleter());
+        }
+
         PluginCommand removeCommand = this.getCommand("removePaidSign");
         if (removeCommand != null) {
             TabExecutor removeTabExecutor = new RemoveTabCommand();
diff --git a/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java b/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java
index a2cbf82..3a6c5ef 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java
@@ -29,6 +29,7 @@ public class AddCommand implements CommandExecutor {
         }
         PaidSignManager manager = PaidSigns.getInstance().getSignManager();
         List<String> arguments = Tokenizer.tokenize(String.join(" ", args));
+        int argumentSize = args[args.length - 1].isEmpty() ? arguments.size() : arguments.size() - 1;
 
         String signName = arguments.get(0);
         double cost;
@@ -41,20 +42,18 @@ public class AddCommand implements CommandExecutor {
         String permission = arguments.get(2);
         OptionState ignoreCase = OptionState.DEFAULT;
         OptionState ignoreColor = OptionState.DEFAULT;
-        if (arguments.size() > 3) {
+        if (argumentSize > 3) {
             ignoreCase = OptionState.fromString(arguments.get(3));
         }
-        if (arguments.size() > 4) {
+        if (argumentSize > 4) {
             ignoreColor = OptionState.fromString(arguments.get(4));
         }
 
         try {
             PaidSign sign = new PaidSign(signName, cost, permission, ignoreCase, ignoreColor);
-            for (PaidSign otherSign : manager.getAllPaidSigns()) {
-                if (sign.getName().equals(otherSign.getName())) {
-                    sender.sendMessage("A paid sign with the same name already exists");
-                    return false;
-                }
+            if (manager.getPaidSign(signName) != null) {
+                sender.sendMessage("A paid sign with the same name already exists");
+                return false;
             }
             manager.addPaidSign(sign);
             sender.sendMessage("Successfully added new paid sign");
diff --git a/src/main/java/net/knarcraft/paidsigns/command/AddConditionCommand.java b/src/main/java/net/knarcraft/paidsigns/command/AddConditionCommand.java
index 8c2345d..745123e 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/AddConditionCommand.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/AddConditionCommand.java
@@ -1,16 +1,56 @@
 package net.knarcraft.paidsigns.command;
 
+import net.knarcraft.paidsigns.PaidSigns;
+import net.knarcraft.paidsigns.container.PaidSign;
+import net.knarcraft.paidsigns.property.OptionState;
+import net.knarcraft.paidsigns.utility.Tokenizer;
 import org.bukkit.command.Command;
 import org.bukkit.command.CommandExecutor;
 import org.bukkit.command.CommandSender;
 import org.jetbrains.annotations.NotNull;
 
+import java.util.List;
+
+/**
+ * A representation of the command for adding a new match condition for a sign
+ */
 public class AddConditionCommand implements CommandExecutor {
 
     @Override
     public boolean onCommand(@NotNull CommandSender sender, @NotNull Command command, @NotNull String label, @NotNull String[] args) {
+        List<String> arguments = Tokenizer.tokenize(String.join(" ", args));
+        int argumentSize = args[args.length - 1].isEmpty() ? arguments.size() : arguments.size() - 1;
+        if (argumentSize < 3) {
+            return false;
+        }
 
-
+        String name = arguments.get(0);
+        short lineNumber;
+        try {
+            lineNumber = (short) (Short.parseShort(arguments.get(1)) - 1);
+        } catch (NumberFormatException exception) {
+            sender.sendMessage("Invalid line number given");
+            return false;
+        }
+        String stringToMatch = arguments.get(2);
+        boolean executeRegEx = false;
+        if (argumentSize > 3) {
+            executeRegEx = Boolean.parseBoolean(arguments.get(3));
+        }
+        OptionState ignoreCase = OptionState.DEFAULT;
+        if (argumentSize > 4) {
+            ignoreCase = OptionState.getFromBoolean(Boolean.parseBoolean(arguments.get(4)));
+        }
+        OptionState ignoreColor = OptionState.DEFAULT;
+        if (argumentSize > 5) {
+            ignoreColor = OptionState.getFromBoolean(Boolean.parseBoolean(arguments.get(5)));
+        }
+        PaidSign sign = PaidSigns.getInstance().getSignManager().getPaidSign(name);
+        if (sign == null) {
+            sender.sendMessage("No such paid sign exists");
+            return false;
+        }
+        sign.addCondition(lineNumber, stringToMatch, executeRegEx, ignoreCase, ignoreColor);
         return false;
     }
 
diff --git a/src/main/java/net/knarcraft/paidsigns/command/AddConditionTabCompleter.java b/src/main/java/net/knarcraft/paidsigns/command/AddConditionTabCompleter.java
new file mode 100644
index 0000000..3e917f5
--- /dev/null
+++ b/src/main/java/net/knarcraft/paidsigns/command/AddConditionTabCompleter.java
@@ -0,0 +1,57 @@
+package net.knarcraft.paidsigns.command;
+
+import net.knarcraft.paidsigns.utility.TabCompleteHelper;
+import net.knarcraft.paidsigns.utility.Tokenizer;
+import org.bukkit.command.Command;
+import org.bukkit.command.CommandSender;
+import org.bukkit.command.TabCompleter;
+import org.jetbrains.annotations.NotNull;
+import org.jetbrains.annotations.Nullable;
+
+import java.util.List;
+
+/**
+ * The tab completer for the add paid sign condition command
+ */
+public class AddConditionTabCompleter implements TabCompleter {
+
+    private List<String> lineIndices;
+    private List<String> stringsToMatch;
+    private List<String> booleans;
+    private List<String> optionStates;
+
+    @Nullable
+    @Override
+    public List<String> onTabComplete(@NotNull CommandSender sender, @NotNull Command command, @NotNull String alias,
+                                      @NotNull String[] args) {
+        if (lineIndices == null) {
+            initializeValues();
+        }
+
+        List<String> arguments = Tokenizer.tokenize(String.join(" ", args));
+        int argumentSize = args[args.length - 1].isEmpty() ? arguments.size() : arguments.size() - 1;
+        if (argumentSize < 1) {
+            return TabCompleteHelper.getPaidSignNames();
+        } else if (argumentSize < 2) {
+            return this.lineIndices;
+        } else if (argumentSize < 3) {
+            return stringsToMatch;
+        } else if (argumentSize < 4) {
+            return booleans;
+        } else if (argumentSize < 6) {
+            return optionStates;
+        }
+        return null;
+    }
+
+    /**
+     * Initializes the values available for tab completion
+     */
+    private void initializeValues() {
+        lineIndices = TabCompleteHelper.getSignLines();
+        stringsToMatch = TabCompleteHelper.getExampleConditionStrings();
+        booleans = TabCompleteHelper.getBooleans();
+        optionStates = TabCompleteHelper.getOptionStates();
+    }
+
+}
diff --git a/src/main/java/net/knarcraft/paidsigns/command/AddTabCompleter.java b/src/main/java/net/knarcraft/paidsigns/command/AddTabCompleter.java
index fa2dea4..7bbc7ce 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/AddTabCompleter.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/AddTabCompleter.java
@@ -1,5 +1,6 @@
 package net.knarcraft.paidsigns.command;
 
+import net.knarcraft.paidsigns.utility.TabCompleteHelper;
 import net.knarcraft.paidsigns.utility.Tokenizer;
 import org.bukkit.Bukkit;
 import org.bukkit.command.Command;
@@ -128,21 +129,9 @@ public class AddTabCompleter implements TabCompleter {
      * Initializes the values available for tab completion
      */
     private static void initializeValues() {
-        names = new ArrayList<>();
-        names.add("sign1");
-        names.add("\"lift up sign\"");
-        names.add("\"lift down sign\"");
-
-        costs = new ArrayList<>();
-        costs.add("1");
-        costs.add("5");
-        costs.add("10");
-        costs.add("15");
-
-        options = new ArrayList<>();
-        options.add("default");
-        options.add("true");
-        options.add("false");
+        names = TabCompleteHelper.getExamplePaidSignNames();
+        costs = TabCompleteHelper.getCosts();
+        options = TabCompleteHelper.getOptionStates();
     }
 
 }
diff --git a/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCommand.java b/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCommand.java
index 6f2cc85..130f2c0 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCommand.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCommand.java
@@ -13,6 +13,7 @@ import java.io.IOException;
 import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.List;
+import java.util.Map;
 import java.util.logging.Level;
 import java.util.logging.Logger;
 
@@ -55,12 +56,12 @@ public class RemoveTabCommand implements TabExecutor {
         int argumentSize = args[args.length - 1].isEmpty() ? arguments.size() : arguments.size() - 1;
 
         if (argumentSize < 1) {
-            List<PaidSign> allPaidSigns = PaidSigns.getInstance().getSignManager().getAllPaidSigns();
-            List<String> signIds = new ArrayList<>();
-            for (PaidSign sign : allPaidSigns) {
-                signIds.add("\"" + sign.getName() + "\"");
+            Map<String, PaidSign> allPaidSigns = PaidSigns.getInstance().getSignManager().getAllPaidSigns();
+            List<String> signNames = new ArrayList<>();
+            for (String name : allPaidSigns.keySet()) {
+                signNames.add("\"" + name + "\"");
             }
-            return signIds;
+            return signNames;
         } else {
             return new ArrayList<>();
         }
diff --git a/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java b/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
index 6724f7d..ceed610 100644
--- a/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
+++ b/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
@@ -9,7 +9,7 @@ import org.bukkit.event.EventPriority;
 import org.bukkit.event.Listener;
 import org.bukkit.event.block.SignChangeEvent;
 
-import java.util.List;
+import java.util.Map;
 
 /**
  * A listener for listening to registered paid signs
@@ -24,8 +24,8 @@ public class SignListener implements Listener {
         }
 
         String[] lines = event.getLines();
-        List<PaidSign> matchingSigns = PaidSigns.getInstance().getSignManager().getAllPaidSigns();
-        for (PaidSign paidSign : matchingSigns) {
+        Map<String, PaidSign> matchingSigns = PaidSigns.getInstance().getSignManager().getAllPaidSigns();
+        for (PaidSign paidSign : matchingSigns.values()) {
             //If a match is found, just return
             if (matchSign(paidSign, lines, event)) {
                 return;
diff --git a/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java b/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
index fe3cfe8..b475329 100644
--- a/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
+++ b/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
@@ -9,8 +9,7 @@ import org.bukkit.configuration.file.YamlConfiguration;
 
 import java.io.File;
 import java.io.IOException;
-import java.util.ArrayList;
-import java.util.List;
+import java.util.HashMap;
 import java.util.Map;
 import java.util.logging.Level;
 
@@ -19,7 +18,7 @@ import java.util.logging.Level;
  */
 public final class PaidSignManager {
 
-    private final List<PaidSign> paidSigns;
+    private final Map<String, PaidSign> paidSigns;
     private static final File signsFile = new File(PaidSigns.getInstance().getDataFolder(), "data.yml");
 
     /**
@@ -27,7 +26,7 @@ public final class PaidSignManager {
      *
      * @param paidSigns <p>The paid signs this manager should manage</p>
      */
-    public PaidSignManager(List<PaidSign> paidSigns) {
+    public PaidSignManager(Map<String, PaidSign> paidSigns) {
         this.paidSigns = paidSigns;
     }
 
@@ -38,7 +37,7 @@ public final class PaidSignManager {
      * @throws IOException <p>If unable to write to the signs file</p>
      */
     public void addPaidSign(PaidSign paidSign) throws IOException {
-        this.paidSigns.add(paidSign);
+        this.paidSigns.put(paidSign.getName(), paidSign);
         saveSigns(this.paidSigns);
     }
 
@@ -50,7 +49,7 @@ public final class PaidSignManager {
      * @throws IOException <p>If unable to write to the signs file</p>
      */
     public boolean removePaidSign(String name) throws IOException {
-        boolean removed = this.paidSigns.removeIf((sign) -> sign.getName().equals(name));
+        boolean removed = this.paidSigns.remove(name) != null;
         if (!removed) {
             return false;
         } else {
@@ -59,13 +58,23 @@ public final class PaidSignManager {
         }
     }
 
+    /**
+     * Gets the paid sign with the given name
+     *
+     * @param name <p>The paid sign with the given name</p>
+     * @return <p>The paid sign with the given name, or null if it does not exist</p>
+     */
+    public PaidSign getPaidSign(String name) {
+        return paidSigns.get(name);
+    }
+
     /**
      * Gets a copy of all registered paid signs
      *
      * @return <p>All registered paid signs</p>
      */
-    public List<PaidSign> getAllPaidSigns() {
-        return new ArrayList<>(paidSigns);
+    public Map<String, PaidSign> getAllPaidSigns() {
+        return new HashMap<>(paidSigns);
     }
 
     /**
@@ -73,15 +82,15 @@ public final class PaidSignManager {
      *
      * @return <p>The loaded paid signs</p>
      */
-    public static List<PaidSign> loadSigns() {
+    public static Map<String, PaidSign> loadSigns() {
         YamlConfiguration configuration = YamlConfiguration.loadConfiguration(signsFile);
         ConfigurationSection signSection = configuration.getConfigurationSection("paidSigns");
         if (signSection == null) {
             PaidSigns.getInstance().getLogger().log(Level.WARNING, "Signs section not found in data.yml");
-            return new ArrayList<>();
+            return new HashMap<>();
         }
 
-        List<PaidSign> paidSigns = new ArrayList<>();
+        Map<String, PaidSign> paidSigns = new HashMap<>();
         for (String name : signSection.getKeys(false)) {
             double cost = signSection.getDouble(name + ".cost");
             String permission = signSection.getString(name + ".permission");
@@ -89,7 +98,7 @@ public final class PaidSignManager {
             OptionState ignoreColor = OptionState.getFromBoolean(signSection.getBoolean(name + ".ignoreColor"));
             PaidSign sign = new PaidSign(name, cost, permission, ignoreCase, ignoreColor);
             loadConditions(signSection, sign);
-            paidSigns.add(sign);
+            paidSigns.put(name, sign);
         }
         return paidSigns;
     }
@@ -122,12 +131,12 @@ public final class PaidSignManager {
      * @param signs <p>The signs to save</p>
      * @throws IOException <p>If unable to write to the signs file</p>
      */
-    public static void saveSigns(List<PaidSign> signs) throws IOException {
+    public static void saveSigns(Map<String, PaidSign> signs) throws IOException {
         YamlConfiguration configuration = YamlConfiguration.loadConfiguration(signsFile);
         ConfigurationSection signSection = configuration.createSection("paidSigns");
 
-        for (PaidSign sign : signs) {
-            String name = sign.getName();
+        for (PaidSign sign : signs.values()) {
+            String name = signSection.getName();
             signSection.set(name + ".cost", sign.getCost());
             signSection.set(name + ".permission", sign.getPermission());
             signSection.set(name + ".ignoreCase", sign.getIgnoreCase());
diff --git a/src/main/java/net/knarcraft/paidsigns/utility/TabCompleteHelper.java b/src/main/java/net/knarcraft/paidsigns/utility/TabCompleteHelper.java
new file mode 100644
index 0000000..a898ca7
--- /dev/null
+++ b/src/main/java/net/knarcraft/paidsigns/utility/TabCompleteHelper.java
@@ -0,0 +1,98 @@
+package net.knarcraft.paidsigns.utility;
+
+import net.knarcraft.paidsigns.PaidSigns;
+
+import java.util.ArrayList;
+import java.util.List;
+
+/**
+ * A helper class for providing common tab complete options
+ */
+public class TabCompleteHelper {
+
+    /**
+     * Gets the available boolean values for tab completion
+     *
+     * @return <p>The available boolean values</p>
+     */
+    public static List<String> getBooleans() {
+        List<String> booleans = new ArrayList<>();
+        booleans.add("true");
+        booleans.add("false");
+        return booleans;
+    }
+
+    /**
+     * Gets the available option states for tab completion
+     *
+     * @return <p>The available option states</p>
+     */
+    public static List<String> getOptionStates() {
+        List<String> optionStates = getBooleans();
+        optionStates.add("default");
+        return optionStates;
+    }
+
+    /**
+     * Gets the names of all registered paid signs
+     *
+     * @return <p>The names of all registered paid signs</p>
+     */
+    public static List<String> getPaidSignNames() {
+        return new ArrayList<>(PaidSigns.getInstance().getSignManager().getAllPaidSigns().keySet());
+    }
+
+    /**
+     * Gets all the choices for lines on a sign
+     *
+     * @return <p>All the line indices of a sign</p>
+     */
+    public static List<String> getSignLines() {
+        List<String> lines = new ArrayList<>();
+        for (int i = 1; i < 5; i++) {
+            lines.add(String.valueOf(i));
+        }
+        return lines;
+    }
+
+    /**
+     * Gets some valid costs as example values
+     *
+     * @return <p>Some valid costs</p>
+     */
+    public static List<String> getCosts() {
+        List<String> costs = new ArrayList<>();
+        costs.add("1");
+        costs.add("5");
+        costs.add("10");
+        costs.add("15");
+        return costs;
+    }
+
+    /**
+     * Gets some example paid sign names for auto-completion
+     *
+     * @return <p>Some example paid sign names</p>
+     */
+    public static List<String> getExamplePaidSignNames() {
+        List<String> names = new ArrayList<>();
+        names.add("sign1");
+        names.add("\"lift up sign\"");
+        names.add("\"lift down sign\"");
+        return names;
+    }
+
+    /**
+     * Gets some example condition matching strings for tab completion
+     *
+     * @return <p>Some example "stringToMatch" values</p>
+     */
+    public static List<String> getExampleConditionStrings() {
+        List<String> conditionStrings = new ArrayList<>();
+        conditionStrings.add("[Gate]");
+        conditionStrings.add("\"[Lift Up]\"");
+        conditionStrings.add("\"[Lift Down]\"");
+        return conditionStrings;
+    }
+
+}