diff --git a/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java b/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java
index a5fe838..f367e74 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/AddCommand.java
@@ -31,15 +31,14 @@ public class AddCommand implements CommandExecutor {
         List<String> arguments = Tokenizer.tokenize(String.join(" ", args));
 
         String id = arguments.get(0);
-        short line;
         double cost;
         try {
-            line = (short) (Short.parseShort(arguments.get(1)) - 1);
             cost = Double.parseDouble(arguments.get(2));
         } catch (NumberFormatException exception) {
             sender.sendMessage("You provided an invalid number");
             return false;
         }
+        String permission = arguments.get(2);
         OptionState ignoreCase = OptionState.DEFAULT;
         OptionState ignoreColor = OptionState.DEFAULT;
         if (arguments.size() > 3) {
@@ -50,13 +49,14 @@ public class AddCommand implements CommandExecutor {
         }
 
         try {
-            PaidSign sign = new PaidSign(id, line, cost, ignoreCase, ignoreColor);
+            PaidSign sign = new PaidSign(id, cost, permission, ignoreCase, ignoreColor);
+            /* TODO: Rewrite the method for comparing if paid signs are duplicated
             for (PaidSign similarSign : manager.getPaidSigns(sign.getCleanId(), sign.getLineIndex())) {
                 if (sign.matches(similarSign)) {
                     sender.sendMessage("A paid sign with the same id and line already exists");
                     return false;
                 }
-            }
+            }*/
             manager.addPaidSign(sign);
             sender.sendMessage("Successfully added new paid sign");
             return true;
diff --git a/src/main/java/net/knarcraft/paidsigns/command/RemoveCommand.java b/src/main/java/net/knarcraft/paidsigns/command/RemoveCommand.java
index f77c007..2e3eef9 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/RemoveCommand.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/RemoveCommand.java
@@ -2,7 +2,6 @@ package net.knarcraft.paidsigns.command;
 
 import net.knarcraft.paidsigns.PaidSigns;
 import net.knarcraft.paidsigns.utility.Tokenizer;
-import org.apache.commons.lang.ArrayUtils;
 import org.bukkit.command.Command;
 import org.bukkit.command.CommandExecutor;
 import org.bukkit.command.CommandSender;
@@ -26,17 +25,10 @@ public class RemoveCommand implements CommandExecutor {
             return false;
         }
         List<String> arguments = Tokenizer.tokenize(String.join(" ", args));
-        String[] input = arguments.get(0).split("\\|");
-        short line;
+        String name = arguments.get(0);
+
         try {
-            line = (short) (Short.parseShort(input[0]) - 1);
-        } catch (NumberFormatException exception) {
-            sender.sendMessage("Invalid line number given");
-            return false;
-        }
-        String id = String.join("|", (String[]) ArrayUtils.remove(input, 0));
-        try {
-            if (PaidSigns.getInstance().getSignManager().removePaidSign(id, line)) {
+            if (PaidSigns.getInstance().getSignManager().removePaidSign(name)) {
                 sender.sendMessage("Successfully removed paid sign");
             } else {
                 sender.sendMessage("No matching paid sign was found");
diff --git a/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCompleter.java b/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCompleter.java
index aaa48c0..187e866 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCompleter.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/RemoveTabCompleter.java
@@ -23,7 +23,7 @@ public class RemoveTabCompleter implements TabCompleter {
         List<PaidSign> allPaidSigns = PaidSigns.getInstance().getSignManager().getAllPaidSigns();
         List<String> signIds = new ArrayList<>();
         for (PaidSign sign : allPaidSigns) {
-            signIds.add("\"" + (sign.getLineIndex() + 1) + "|" + sign.getId() + "\"");
+            signIds.add("\"" + sign.getName() + "\"");
         }
         return signIds;
     }
diff --git a/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java b/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java
index 3e9e6ff..e2c74a1 100644
--- a/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java
+++ b/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java
@@ -2,58 +2,55 @@ package net.knarcraft.paidsigns.container;
 
 import net.knarcraft.paidsigns.PaidSigns;
 import net.knarcraft.paidsigns.property.OptionState;
-import net.knarcraft.paidsigns.utility.ColorHelper;
-import net.md_5.bungee.api.ChatColor;
+
+import java.util.HashMap;
+import java.util.Map;
 
 /**
  * A representation of a paid sign
  */
 public class PaidSign {
 
-    private final String id;
-    private final String cleanId;
-    private final short lineIndex;
+    private final String name;
     private final double cost;
+    private final String permission;
     private final OptionState ignoreCase;
     private final OptionState ignoreColor;
+    private final Map<Short, PaidSignCondition> conditions = new HashMap<>();
 
     /**
      * Instantiates a new paid sign
      *
-     * @param id          <p>The string that identifies this type of paid sign</p>
-     * @param lineIndex   <p>The line the id has to be on to trigger payment</p>
+     * @param name        <p>A recognizable, unique, name used to identify this paid sign</p>
      * @param cost        <p>The cost of creating this paid sign</p>
+     * @param permission  <p>The permission required to create the sign this paid sign matches</p>
      * @param ignoreCase  <p>Whether to ignore case when looking for this permission sign</p>
      * @param ignoreColor <p>Whether to ignore color when looking for this permission sign</p>
      */
-    public PaidSign(String id, short lineIndex, double cost, OptionState ignoreCase, OptionState ignoreColor) {
-        if (id == null || id.trim().isBlank()) {
+    public PaidSign(String name, double cost, String permission, OptionState ignoreCase, OptionState ignoreColor) {
+        if (name == null || name.trim().isBlank()) {
             throw new IllegalArgumentException("Id cannot be empty");
         }
         if (cost <= 0) {
             throw new IllegalArgumentException("Cost must be larger than 0");
         }
-        if (lineIndex < 0 || lineIndex > 3) {
-            throw new IllegalArgumentException("Sign line must be between 0 and 3");
-        }
         if (ignoreCase == null || ignoreColor == null) {
             throw new IllegalArgumentException("Ignore case and ignore color options cannot be null");
         }
-        this.id = id;
-        this.lineIndex = lineIndex;
+        this.name = name;
         this.cost = cost;
+        this.permission = permission;
         this.ignoreCase = ignoreCase;
         this.ignoreColor = ignoreColor;
-        this.cleanId = getCleanString(id);
     }
 
     /**
-     * Gets the id string of this paid sign
+     * Gets the name identifying this paid sign
      *
-     * @return <p>The id string of this paid sign</p>
+     * @return <p>The name identifying this paid sign</p>
      */
-    public String getId() {
-        return id;
+    public String getName() {
+        return name;
     }
 
     /**
@@ -66,66 +63,21 @@ public class PaidSign {
     }
 
     /**
-     * Gets the line on the sign the id must be on to trigger payment
+     * Gets the permission required by a player to create the sign this paid sign matches
      *
-     * @return <p>The sign line to search for the id</p>
+     * @return <p>The permission required by a player to create the sign this paid sign matches</p>
      */
-    public short getLineIndex() {
-        return lineIndex;
+    public String getPermission() {
+        return this.permission;
     }
 
     /**
-     * Gets the clean id of this paid sign
+     * Gets all conditions registered for this paid sign
      *
-     * @return <p>The clean id of this paid sign</p>
+     * @return <p>All conditions registered for this paid sign</p>
      */
-    public String getCleanId() {
-        return cleanId;
-    }
-
-    /**
-     * Gets the "clean" version of the given string
-     *
-     * <p>The "cleaning" removes color codes and lower-cases the string.</p>
-     *
-     * @param string <p>The string to clean</p>
-     * @return <p>The cleaned string</p>
-     */
-    public static String getCleanString(String string) {
-        return ChatColor.stripColor(ColorHelper.translateAllColorCodes(string.toLowerCase()));
-    }
-
-    /**
-     * Checks whether this paid sign matches the given line
-     *
-     * @param lineNumber <p>The line number of the given line</p>
-     * @param line       <p>The line to compare against this paid sign's id</p>
-     * @return <p>True if the line matches this sign</p>
-     */
-    public boolean matches(short lineNumber, String line) {
-        if (lineNumber != this.lineIndex) {
-            return false;
-        }
-        String idCopy = id;
-        if (getIgnoreCase()) {
-            idCopy = idCopy.toLowerCase();
-            line = line.toLowerCase();
-        }
-        if (getIgnoreColor()) {
-            idCopy = ColorHelper.stripColorCodes(idCopy);
-            line = ColorHelper.stripColorCodes(line);
-        }
-        return idCopy.equals(line);
-    }
-
-    /**
-     * Checks whether this paid sign matches another paid sign
-     *
-     * @param paidSign <p>The other paid sign to compare to</p>
-     * @return <p>True if the signs match</p>
-     */
-    public boolean matches(PaidSign paidSign) {
-        return matches(paidSign.lineIndex, paidSign.id);
+    public Map<Short, PaidSignCondition> getConditions() {
+        return new HashMap<>(this.conditions);
     }
 
     /**
@@ -134,11 +86,7 @@ public class PaidSign {
      * @return <p>Whether the text case should be ignored for this paid sign</p>
      */
     public boolean getIgnoreCase() {
-        if (this.ignoreCase == OptionState.DEFAULT) {
-            return PaidSigns.getInstance().ignoreCase();
-        } else {
-            return OptionState.getBooleanValue(this.ignoreCase);
-        }
+        return OptionState.getBooleanValue(this.ignoreCase, PaidSigns.getInstance().ignoreCase());
     }
 
     /**
@@ -147,11 +95,46 @@ public class PaidSign {
      * @return <p>Whether the text color should be ignored for this paid sign</p>
      */
     public boolean getIgnoreColor() {
-        if (this.ignoreColor == OptionState.DEFAULT) {
-            return PaidSigns.getInstance().ignoreColor();
-        } else {
-            return OptionState.getBooleanValue(this.ignoreColor);
+        return OptionState.getBooleanValue(this.ignoreColor, PaidSigns.getInstance().ignoreColor());
+    }
+
+    /**
+     * Checks whether this paid sign matches the given set of sign lines
+     *
+     * @param lines <p>The sign lines to test against</p>
+     * @return <p>True if this paid sign matches the given lines</p>
+     */
+    public boolean matches(String[] lines) {
+        //Make sure a paid sign without a condition never matches anything
+        if (this.conditions.isEmpty()) {
+            return false;
         }
+        boolean success = true;
+        for (short i = 0; i < 4; i++) {
+            PaidSignCondition condition = this.conditions.get(i);
+            if (condition != null) {
+                success = success && condition.test(lines[i]);
+            }
+        }
+        return success;
+    }
+
+    /**
+     * Adds a condition to this paid sign
+     *
+     * @param line          <p>The line on the sign the matched text must be on</p>
+     * @param stringToMatch <p>The string that should be matched for the new condition to be true</p>
+     * @param executeRegex  <p>Whether to execute the string as RegEx</p>
+     * @param ignoreCase    <p>Whether to ignore case when matching against the condition</p>
+     * @param ignoreColor   <p>Whether to ignore color when matching against the condition</p>
+     */
+    public void addCondition(short line, String stringToMatch, boolean executeRegex, OptionState ignoreCase, OptionState ignoreColor) {
+        if (line < 0 || line > 3) {
+            throw new IllegalArgumentException("Invalid sign line given for new paid sign condition");
+        }
+        boolean ignoreCaseBoolean = OptionState.getBooleanValue(ignoreCase, this.getIgnoreCase());
+        boolean ignoreColorBoolean = OptionState.getBooleanValue(ignoreColor, this.getIgnoreColor());
+        this.conditions.put(line, new PaidSignCondition(stringToMatch, executeRegex, ignoreCaseBoolean, ignoreColorBoolean));
     }
 
 }
diff --git a/src/main/java/net/knarcraft/paidsigns/container/PaidSignCondition.java b/src/main/java/net/knarcraft/paidsigns/container/PaidSignCondition.java
new file mode 100644
index 0000000..7cf7df5
--- /dev/null
+++ b/src/main/java/net/knarcraft/paidsigns/container/PaidSignCondition.java
@@ -0,0 +1,96 @@
+package net.knarcraft.paidsigns.container;
+
+import net.knarcraft.paidsigns.utility.ColorHelper;
+
+/**
+ * A condition for deciding if a paid sign matches a sign line
+ */
+public class PaidSignCondition {
+
+    final String stringToMatch;
+    final boolean executeRegex;
+    final boolean ignoreCase;
+    final boolean ignoreColor;
+
+    /**
+     * Instantiates a new paid sign condition
+     *
+     * @param stringToMatch <p>The string/regular expression the line has to match to fulfill this condition</p>
+     * @param executeRegex  <p>Whether to execute the match string as a regular expression</p>
+     * @param ignoreCase    <p>Whether to ignore uppercase/lowercase when comparing against this condition</p>
+     * @param ignoreColor   <p>Whether to ignore color codes when comparing against this condition</p>
+     */
+    public PaidSignCondition(String stringToMatch, boolean executeRegex, boolean ignoreCase, boolean ignoreColor) {
+        this.stringToMatch = stringToMatch;
+        this.executeRegex = executeRegex;
+        this.ignoreCase = ignoreCase;
+        this.ignoreColor = ignoreColor;
+    }
+
+    /**
+     * Gets the string this condition should match
+     *
+     * @return <p>The string this condition should match</p>
+     */
+    public String getStringToMatch() {
+        return this.stringToMatch;
+    }
+
+    /**
+     * Gets whether to execute the match string as RegEx
+     *
+     * @return <p>Whether to execute the match string as RegEx</p>
+     */
+    public boolean executeRegex() {
+        return this.executeRegex;
+    }
+
+    /**
+     * Gets whether to ignore case when trying to match strings
+     *
+     * @return <p>Whether to ignore case when trying to match strings</p>
+     */
+    public boolean ignoreCase() {
+        return this.ignoreCase;
+    }
+
+    /**
+     * Gets whether to ignore color when trying to match strings
+     *
+     * @return <p>Whether to ignore color when trying to match strings</p>
+     */
+    public boolean ignoreColor() {
+        return this.ignoreColor;
+    }
+
+    /**
+     * Tests whether the given line matches this condition
+     *
+     * @param line <p>The sign line to test</p>
+     * @return <p>True if this condition matches the given line</p>
+     */
+    public boolean test(String line) {
+        String stringToMatch = this.stringToMatch;
+        //Strip color codes if they shouldn't matter
+        if (this.ignoreColor) {
+            stringToMatch = ColorHelper.stripColorCodes(stringToMatch);
+            line = ColorHelper.stripColorCodes(line);
+        }
+        if (this.executeRegex) {
+            //Match using RegEx
+            if (this.ignoreCase) {
+                return line.matches("(?i)" + stringToMatch);
+            } else {
+                return line.matches(stringToMatch);
+            }
+        } else {
+            //Match regularly
+            if (this.ignoreCase) {
+                return stringToMatch.equalsIgnoreCase(line);
+            } else {
+                return stringToMatch.equals(line);
+            }
+        }
+    }
+
+}
diff --git a/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java b/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
index ddec22c..6724f7d 100644
--- a/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
+++ b/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
@@ -3,7 +3,6 @@ package net.knarcraft.paidsigns.listener;
 import net.knarcraft.paidsigns.PaidSigns;
 import net.knarcraft.paidsigns.container.PaidSign;
 import net.knarcraft.paidsigns.manager.EconomyManager;
-import net.knarcraft.paidsigns.manager.PaidSignManager;
 import org.bukkit.entity.Player;
 import org.bukkit.event.EventHandler;
 import org.bukkit.event.EventPriority;
@@ -17,51 +16,51 @@ import java.util.List;
  */
 public class SignListener implements Listener {
 
-    @EventHandler(priority = EventPriority.MONITOR)
+    @EventHandler(priority = EventPriority.LOW)
+    @SuppressWarnings("unused")
     public void onSignChange(SignChangeEvent event) {
         if (event.isCancelled() || event.getPlayer().hasPermission("paidsigns.paymentexempt")) {
             return;
         }
 
         String[] lines = event.getLines();
-        PaidSignManager signManager = PaidSigns.getInstance().getSignManager();
-        for (short lineIndex = 0; lineIndex < lines.length; lineIndex++) {
-            //Get all "weak" matches (any paid sign with a clean id matching the clean line)
-            List<PaidSign> matchingSigns = signManager.getPaidSigns(PaidSign.getCleanString(lines[lineIndex]), lineIndex);
-            if (matchingSigns.isEmpty()) {
-                continue;
-            }
-            if (testMatchingSigns(lineIndex, lines[lineIndex], matchingSigns, event)) {
+        List<PaidSign> matchingSigns = PaidSigns.getInstance().getSignManager().getAllPaidSigns();
+        for (PaidSign paidSign : matchingSigns) {
+            //If a match is found, just return
+            if (matchSign(paidSign, lines, event)) {
                 return;
             }
         }
     }
 
     /**
-     * Tests all weak matches of paid signs to check if a strong match is found
+     * Checks if the given paid sign matches the given sign lines
      *
-     * @param lineIndex     <p>The index of the currently managed line</p>
-     * @param line          <p>The text on the currently managed line</p>
-     * @param matchingSigns <p>The signs that weakly match the </p>
-     * @param event         <p>The triggered sign change event</p>
-     * @return <p>True if a match was found and thw work is finished</p>
+     * @param paidSign <p>The paid sign to test against the sign lines</p>
+     * @param lines    <p>The lines of a sign</p>
+     * @param event    <p>The triggered sign change event to cancel if necessary</p>
+     * @return <p>True if a match was found and actions have been taken</p>
      */
-    private boolean testMatchingSigns(short lineIndex, String line, List<PaidSign> matchingSigns, SignChangeEvent event) {
-        for (PaidSign paidSign : matchingSigns) {
-            if (paidSign.matches(lineIndex, line)) {
-                Player player = event.getPlayer();
-                double cost = paidSign.getCost();
-                boolean canAfford = EconomyManager.canAfford(player, cost);
-                if (!canAfford) {
-                    player.sendMessage("[PaidSigns] You cannot afford to create this sign");
-                    event.setCancelled(true);
-                } else {
-                    String unit = EconomyManager.getCurrency(cost != 1);
-                    player.sendMessage(String.format("[PaidSigns] You paid %.2f %s to create the sign", cost, unit));
-                    EconomyManager.withdraw(player, cost);
-                }
+    private boolean matchSign(PaidSign paidSign, String[] lines, SignChangeEvent event) {
+        if (paidSign.matches(lines)) {
+            Player player = event.getPlayer();
+            String permission = paidSign.getPermission();
+            //If a match is found, but the player is missing the permission, assume no plugin sign was created
+            if (permission != null && !permission.trim().isEmpty() && !player.hasPermission(permission)) {
                 return true;
             }
+
+            double cost = paidSign.getCost();
+            boolean canAfford = EconomyManager.canAfford(player, cost);
+            if (!canAfford) {
+                player.sendMessage("[PaidSigns] You cannot afford to create this sign");
+                event.setCancelled(true);
+            } else {
+                String unit = EconomyManager.getCurrency(cost != 1);
+                player.sendMessage(String.format("[PaidSigns] You paid %.2f %s to create the sign", cost, unit));
+                EconomyManager.withdraw(player, cost);
+            }
+            return true;
         }
         return false;
     }
diff --git a/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java b/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
index 4fbbe70..fe3cfe8 100644
--- a/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
+++ b/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
@@ -2,6 +2,7 @@ package net.knarcraft.paidsigns.manager;
 
 import net.knarcraft.paidsigns.PaidSigns;
 import net.knarcraft.paidsigns.container.PaidSign;
+import net.knarcraft.paidsigns.container.PaidSignCondition;
 import net.knarcraft.paidsigns.property.OptionState;
 import org.bukkit.configuration.ConfigurationSection;
 import org.bukkit.configuration.file.YamlConfiguration;
@@ -10,7 +11,7 @@ import java.io.File;
 import java.io.IOException;
 import java.util.ArrayList;
 import java.util.List;
-import java.util.function.Predicate;
+import java.util.Map;
 import java.util.logging.Level;
 
 /**
@@ -20,7 +21,6 @@ public final class PaidSignManager {
 
     private final List<PaidSign> paidSigns;
     private static final File signsFile = new File(PaidSigns.getInstance().getDataFolder(), "data.yml");
-    private static final String signLineIdSeparator = "-,_,-";
 
     /**
      * Instantiate a new paid sign manager
@@ -45,29 +45,18 @@ public final class PaidSignManager {
     /**
      * Removes a paid sign from this paid sign manager
      *
-     * @param id   <p>The identifier for the paid sign to remove</p>
-     * @param line <p>The line the identifier has to match to be valid</p>
+     * @param name <p>The name of the paid sign to remove</p>
      * @return <p>True if a sign was removed</p>
      * @throws IOException <p>If unable to write to the signs file</p>
      */
-    public boolean removePaidSign(String id, short line) throws IOException {
-        boolean removed = this.paidSigns.removeIf((sign) -> sign.getId().equals(id) && sign.getLineIndex() == line);
+    public boolean removePaidSign(String name) throws IOException {
+        boolean removed = this.paidSigns.removeIf((sign) -> sign.getName().equals(name));
         if (!removed) {
             return false;
+        } else {
+            saveSigns(this.paidSigns);
+            return true;
         }
-        saveSigns(this.paidSigns);
-        return true;
-    }
-
-    /**
-     * Gets the paid signs that match the given properties
-     *
-     * @param cleanId <p>The clean id to search for</p>
-     * @param line    <p>The line number to search for</p>
-     * @return <p>The paid signs that matched the given properties</p>
-     */
-    public List<PaidSign> getPaidSigns(String cleanId, short line) {
-        return filterPaidSigns(filterPaidSigns(paidSigns, line), cleanId);
     }
 
     /**
@@ -79,17 +68,6 @@ public final class PaidSignManager {
         return new ArrayList<>(paidSigns);
     }
 
-    /**
-     * Filters a list of paid signs to match the given line number
-     *
-     * @param paidSigns <p>The list of paid signs to start with</p>
-     * @param line      <p>The line number to filter by</p>
-     * @return <p>The filtered list of paid signs</p>
-     */
-    private static List<PaidSign> filterPaidSigns(List<PaidSign> paidSigns, short line) {
-        return filterPaidSigns(paidSigns, (paidSign) -> paidSign.getLineIndex() == line);
-    }
-
     /**
      * Loads paid signs from the signs file
      *
@@ -104,18 +82,40 @@ public final class PaidSignManager {
         }
 
         List<PaidSign> paidSigns = new ArrayList<>();
-        for (String combinedId : signSection.getKeys(false)) {
-            String[] idParts = combinedId.split(signLineIdSeparator);
-            short lineNumber = Short.parseShort(idParts[0]);
-            String id = idParts[1];
-            double cost = signSection.getDouble(combinedId + ".cost");
-            OptionState ignoreCase = OptionState.getFromBoolean(signSection.getBoolean(combinedId + ".ignoreCase"));
-            OptionState ignoreColor = OptionState.getFromBoolean(signSection.getBoolean(combinedId + ".ignoreColor"));
-            paidSigns.add(new PaidSign(id, lineNumber, cost, ignoreCase, ignoreColor));
+        for (String name : signSection.getKeys(false)) {
+            double cost = signSection.getDouble(name + ".cost");
+            String permission = signSection.getString(name + ".permission");
+            OptionState ignoreCase = OptionState.getFromBoolean(signSection.getBoolean(name + ".ignoreCase"));
+            OptionState ignoreColor = OptionState.getFromBoolean(signSection.getBoolean(name + ".ignoreColor"));
+            PaidSign sign = new PaidSign(name, cost, permission, ignoreCase, ignoreColor);
+            loadConditions(signSection, sign);
+            paidSigns.add(sign);
         }
         return paidSigns;
     }
 
+    /**
+     * Loads any saved paid sign conditions and applies them to the given sign
+     *
+     * @param signSection <p>The configuration section containing sign information</p>
+     * @param sign        <p>The sign to load conditions for</p>
+     */
+    private static void loadConditions(ConfigurationSection signSection, PaidSign sign) {
+        ConfigurationSection conditionSection = signSection.getConfigurationSection(sign.getName() + ".conditions");
+        if (conditionSection != null) {
+            for (String lineIndex : conditionSection.getKeys(false)) {
+                short lineNumber = Short.parseShort(lineIndex);
+                String stringToMatch = conditionSection.getString(lineIndex + ".stringToMatch");
+                boolean executeRegEx = conditionSection.getBoolean(lineIndex + ".executeRegEx");
+                boolean ignoreConditionCase = conditionSection.getBoolean(lineIndex + ".ignoreCase");
+                boolean ignoreConditionColor = conditionSection.getBoolean(lineIndex + ".ignoreColor");
+                sign.addCondition(lineNumber, stringToMatch, executeRegEx,
+                        OptionState.getFromBoolean(ignoreConditionCase),
+                        OptionState.getFromBoolean(ignoreConditionColor));
+            }
+        }
+    }
+
     /**
      * Saves the given paid signs to the signs file
      *
@@ -127,34 +127,22 @@ public final class PaidSignManager {
         ConfigurationSection signSection = configuration.createSection("paidSigns");
 
         for (PaidSign sign : signs) {
-            String signId = sign.getLineIndex() + signLineIdSeparator + sign.getId();
-            signSection.set(signId + ".cost", sign.getCost());
-            signSection.set(signId + ".ignoreCase", sign.getIgnoreCase());
-            signSection.set(signId + ".ignoreColor", sign.getIgnoreColor());
+            String name = sign.getName();
+            signSection.set(name + ".cost", sign.getCost());
+            signSection.set(name + ".permission", sign.getPermission());
+            signSection.set(name + ".ignoreCase", sign.getIgnoreCase());
+            signSection.set(name + ".ignoreColor", sign.getIgnoreColor());
+            ConfigurationSection conditionsSection = signSection.createSection(name + ".conditions");
+            Map<Short, PaidSignCondition> signConditions = sign.getConditions();
+            for (short lineIndex : signConditions.keySet()) {
+                PaidSignCondition condition = signConditions.get(lineIndex);
+                conditionsSection.set(lineIndex + ".stringToMatch", condition.getStringToMatch());
+                conditionsSection.set(lineIndex + ".executeRegEx", condition.executeRegex());
+                conditionsSection.set(lineIndex + ".ignoreCase", condition.ignoreCase());
+                conditionsSection.set(lineIndex + ".ignoreColor", condition.ignoreColor());
+            }
         }
         configuration.save(signsFile);
     }
 
-    /**
-     * Filters a list of paid signs to match the given clean id
-     *
-     * @param paidSigns <p>The list of paid signs to start with</p>
-     * @param cleanId   <p>The clean id to filter by</p>
-     * @return <p>The filtered list of paid signs</p>
-     */
-    private static List<PaidSign> filterPaidSigns(List<PaidSign> paidSigns, String cleanId) {
-        return filterPaidSigns(paidSigns, (paidSign) -> paidSign.getCleanId().equals(cleanId));
-    }
-
-    /**
-     * Filters a list of paid signs using the given predicate
-     *
-     * @param paidSigns <p>The list of paid signs to start with</p>
-     * @param predicate <p>The predicate used to filter paid signs</p>
-     * @return <p>The filtered list of paid signs</p>
-     */
-    private static List<PaidSign> filterPaidSigns(List<PaidSign> paidSigns, Predicate<PaidSign> predicate) {
-        return new ArrayList<>(paidSigns).stream().filter(predicate).toList();
-    }
-
 }
diff --git a/src/main/java/net/knarcraft/paidsigns/property/OptionState.java b/src/main/java/net/knarcraft/paidsigns/property/OptionState.java
index e39f5aa..b0e8f61 100644
--- a/src/main/java/net/knarcraft/paidsigns/property/OptionState.java
+++ b/src/main/java/net/knarcraft/paidsigns/property/OptionState.java
@@ -23,14 +23,15 @@ public enum OptionState {
     /**
      * Gets the boolean value of the given option state if it's boolean compatible
      *
-     * @param optionState <p>The option state to get the boolean from</p>
-     * @return <p>The boolean value, or an illegal argument exception if called on DEFAULT</p>
+     * @param optionState  <p>The option state to get the boolean from</p>
+     * @param defaultValue <p>The default value to use if the option state is DEFAULT</p>
+     * @return <p>The boolean value</p>
      */
-    public static boolean getBooleanValue(OptionState optionState) {
+    public static boolean getBooleanValue(OptionState optionState, boolean defaultValue) {
         return switch (optionState) {
             case TRUE -> true;
             case FALSE -> false;
-            case DEFAULT -> throw new IllegalArgumentException("No boolean value available for DEFAULT");
+            case DEFAULT -> defaultValue;
         };
     }