diff --git a/src/main/java/net/knarcraft/paidsigns/command/EditCommand.java b/src/main/java/net/knarcraft/paidsigns/command/EditCommand.java
index c5a8d67..ca7005e 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/EditCommand.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/EditCommand.java
@@ -130,7 +130,7 @@ public class EditCommand extends TokenizedCommand {
         PaidSign updatedSign = new PaidSign(signName, cost, permission, ignoreCase, ignoreColor, matchAnyCondition);
         for (short line : conditions.keySet()) {
             PaidSignCondition condition = conditions.get(line);
-            updatedSign.addCondition(line, condition.getStringToMatch(), condition.executeRegex(),
+            updatedSign.addCondition(line, condition.stringToMatch(), condition.executeRegex(),
                     OptionState.getFromBoolean(condition.ignoreCase()),
                     OptionState.getFromBoolean(condition.ignoreColor()));
         }
@@ -154,7 +154,7 @@ public class EditCommand extends TokenizedCommand {
                                             PaidSignConditionProperty property, String newValue) {
         PaidSignCondition condition = sign.getConditions().get(conditionIndex);
         String stringToMatch = property == PaidSignConditionProperty.STRING_TO_MATCH ? newValue :
-                condition.getStringToMatch();
+                condition.stringToMatch();
         boolean executeRegEx = property == PaidSignConditionProperty.EXECUTE_REG_EX ? Boolean.parseBoolean(newValue) :
                 condition.executeRegex();
         boolean ignoreCase = property == PaidSignConditionProperty.IGNORE_CASE ? OptionState.getBooleanValue(
diff --git a/src/main/java/net/knarcraft/paidsigns/command/ListCommand.java b/src/main/java/net/knarcraft/paidsigns/command/ListCommand.java
index 15d3361..56717f6 100644
--- a/src/main/java/net/knarcraft/paidsigns/command/ListCommand.java
+++ b/src/main/java/net/knarcraft/paidsigns/command/ListCommand.java
@@ -107,7 +107,7 @@ public class ListCommand extends TokenizedCommand {
                                           PaidSignCondition condition) {
         sender.sendMessage(StringFormatter.replacePlaceholders(Translator.getTranslatedMessage(
                 TranslatableMessage.PAID_SIGN_CONDITION_INFO), new String[]{"{name}", "{line}", "{match}", "{regex}",
-                "{case}", "{color}"}, new String[]{signName, String.valueOf(signLine + 1), condition.getStringToMatch(),
+                "{case}", "{color}"}, new String[]{signName, String.valueOf(signLine + 1), condition.stringToMatch(),
                 translateBoolean(condition.executeRegex()), translateBoolean(condition.ignoreCase()),
                 translateBoolean(condition.ignoreColor())}));
     }
@@ -124,7 +124,7 @@ public class ListCommand extends TokenizedCommand {
         for (short lineIndex : signConditions.keySet()) {
             String format = Translator.getTranslatedMessage(TranslatableMessage.PAID_SIGN_INFO_CONDITION_FORMAT);
             conditions.append(StringFormatter.replacePlaceholders(format, new String[]{"{line}", "{condition}"},
-                    new String[]{String.valueOf((lineIndex + 1)), signConditions.get(lineIndex).getStringToMatch()}));
+                    new String[]{String.valueOf((lineIndex + 1)), signConditions.get(lineIndex).stringToMatch()}));
         }
 
         sender.sendMessage(replacePlaceholders(Translator.getTranslatedMessage(
diff --git a/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java b/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java
index 18a3223..e16e4d8 100644
--- a/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java
+++ b/src/main/java/net/knarcraft/paidsigns/container/PaidSign.java
@@ -148,13 +148,15 @@ public class PaidSign {
      * @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) {
+    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));
+        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
index 7cf7df5..9ac4b7b 100644
--- a/src/main/java/net/knarcraft/paidsigns/container/PaidSignCondition.java
+++ b/src/main/java/net/knarcraft/paidsigns/container/PaidSignCondition.java
@@ -4,64 +4,14 @@ import net.knarcraft.paidsigns.utility.ColorHelper;
 
 /**
  * A condition for deciding if a paid sign matches a sign line
+ *
+ * @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 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;
-    }
+public record PaidSignCondition(String stringToMatch, boolean executeRegex, boolean ignoreCase,
+                                boolean ignoreColor) {
 
     /**
      * Tests whether the given line matches this condition
diff --git a/src/main/java/net/knarcraft/paidsigns/container/PaidSignConditionMatch.java b/src/main/java/net/knarcraft/paidsigns/container/PaidSignConditionMatch.java
new file mode 100644
index 0000000..8a28c0d
--- /dev/null
+++ b/src/main/java/net/knarcraft/paidsigns/container/PaidSignConditionMatch.java
@@ -0,0 +1,19 @@
+package net.knarcraft.paidsigns.container;
+
+import org.jetbrains.annotations.NotNull;
+
+/**
+ * A container class for number of condition matches for a paid sign
+ *
+ * @param paidSign         <p>The paid sign this class keeps track of matches for</p>
+ * @param conditionMatches <p>The number of conditions matched for the paid sign</p>
+ */
+public record PaidSignConditionMatch(PaidSign paidSign,
+                                     int conditionMatches) implements Comparable<PaidSignConditionMatch> {
+
+    @Override
+    public int compareTo(@NotNull PaidSignConditionMatch other) {
+        return Integer.compare(this.conditionMatches, other.conditionMatches);
+    }
+
+}
diff --git a/src/main/java/net/knarcraft/paidsigns/container/TrackedSign.java b/src/main/java/net/knarcraft/paidsigns/container/TrackedSign.java
index a050ea7..0b5b290 100644
--- a/src/main/java/net/knarcraft/paidsigns/container/TrackedSign.java
+++ b/src/main/java/net/knarcraft/paidsigns/container/TrackedSign.java
@@ -4,39 +4,10 @@ import java.util.UUID;
 
 /**
  * A representation of a sign placed by a player that matched a paid sign
+ *
+ * @param playerId <p>The unique id of the player that created the sign</p>
+ * @param cost     <p>The cost the player paid for creating the sign</p>
  */
-public class TrackedSign {
-
-    private final UUID playerId;
-    private final double cost;
-
-    /**
-     * Instantiates a new tracked sign
-     *
-     * @param playerId <p>The unique id of the player that created the sign</p>
-     * @param cost     <p>The cost the player paid for creating the sign</p>
-     */
-    public TrackedSign(UUID playerId, double cost) {
-        this.playerId = playerId;
-        this.cost = cost;
-    }
-
-    /**
-     * Gets the id of the player that created this tracked sign
-     *
-     * @return <p>The player that created this tracked sign</p>
-     */
-    public UUID getPlayerId() {
-        return this.playerId;
-    }
-
-    /**
-     * Gets the cost the player paid for creating this paid sign
-     *
-     * @return <p>The cost paid for creating this sign</p>
-     */
-    public double getCost() {
-        return this.cost;
-    }
+public record TrackedSign(UUID playerId, double cost) {
 
 }
diff --git a/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java b/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
index d469966..a3db905 100644
--- a/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
+++ b/src/main/java/net/knarcraft/paidsigns/listener/SignListener.java
@@ -2,6 +2,7 @@ package net.knarcraft.paidsigns.listener;
 
 import net.knarcraft.paidsigns.PaidSigns;
 import net.knarcraft.paidsigns.container.PaidSign;
+import net.knarcraft.paidsigns.container.PaidSignConditionMatch;
 import net.knarcraft.paidsigns.formatting.StringFormatter;
 import net.knarcraft.paidsigns.formatting.TranslatableMessage;
 import net.knarcraft.paidsigns.manager.EconomyManager;
@@ -13,6 +14,9 @@ import org.bukkit.event.Listener;
 import org.bukkit.event.block.SignChangeEvent;
 
 import java.io.IOException;
+import java.util.ArrayList;
+import java.util.Collections;
+import java.util.List;
 import java.util.Map;
 
 /**
@@ -28,36 +32,90 @@ public class SignListener implements Listener {
         }
 
         String[] lines = event.getLines();
-        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;
-            }
+        Map<String, PaidSign> allPaidSigns = PaidSigns.getInstance().getSignManager().getAllPaidSigns();
+
+        //Generate the sorted list of the number of paid sign conditions matched for every paid sign
+        List<PaidSignConditionMatch> allConditionMatches = new ArrayList<>();
+        for (PaidSign paidSign : allPaidSigns.values()) {
+            calculateConditionMatches(paidSign, lines, allConditionMatches);
+        }
+        allConditionMatches.sort(Collections.reverseOrder());
+
+        //Make the player pay for the paid sign
+        PaidSign mostExpensive = getMatchingSign(allConditionMatches);
+        if (mostExpensive != null) {
+            performPaidSignCheck(mostExpensive, event);
         }
     }
 
     /**
-     * Checks if the given paid sign matches the given sign lines
+     * Gets the most specific paid sign match
+     *
+     * <p>This method chooses the most specific match, if any. If two matches have the same number of matched
+     * conditions, it will choose the most expensive one.</p>
+     *
+     * @param allConditionMatches <p>A sorted list of all paid sign condition matches</p>
+     * @return <p>The best matching paid sign, or null if no paid sign matches</p>
+     */
+    private PaidSign getMatchingSign(List<PaidSignConditionMatch> allConditionMatches) {
+        PaidSign mostExpensive = null;
+        int bestMatch = 1;
+        for (PaidSignConditionMatch paidSignConditionMatch : allConditionMatches) {
+            int conditionMatches = paidSignConditionMatch.conditionMatches();
+            /* Stop if there is no matching paid signs. Also stop if a paid sign is encountered with fewer conditions 
+            matching */
+            if (conditionMatches >= bestMatch) {
+                PaidSign paidSign = paidSignConditionMatch.paidSign();
+                //Choose the most expensive paid sign between those with the same number of matched conditions
+                if (mostExpensive == null || paidSign.getCost() > mostExpensive.getCost()) {
+                    mostExpensive = paidSign;
+                    bestMatch = conditionMatches;
+                }
+            } else {
+                break;
+            }
+        }
+        return mostExpensive;
+    }
+
+    /**
+     * Calculates the number of conditions matching for the given paid sign
+     *
+     * <p>This calculates the number of matches, allowing the most specific paid sign to be chosen</p>
+     *
+     * @param paidSign            <p>The paid sign to calculate matches for</p>
+     * @param lines               <p>The lines of a sign</p>
+     * @param allConditionMatches <p>The number of conditions matched</p>
+     */
+    private void calculateConditionMatches(PaidSign paidSign, String[] lines, List<PaidSignConditionMatch> allConditionMatches) {
+        if (paidSign.matches(lines)) {
+            if (paidSign.matchAnyCondition()) {
+                //For any match, it can only be assumed one lines matches
+                allConditionMatches.add(new PaidSignConditionMatch(paidSign, 1));
+            } else {
+                //For a normal match, the number of conditions is equal to the number of matches
+                allConditionMatches.add(new PaidSignConditionMatch(paidSign, paidSign.getConditions().size()));
+            }
+        } else {
+            allConditionMatches.add(new PaidSignConditionMatch(paidSign, 0));
+        }
+    }
+
+    /**
+     * Performs necessary checks and performs the paid sign transaction
      *
      * @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 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;
-            }
-
-            performPaidSignTransaction(paidSign, player, event);
-            return true;
+    private void performPaidSignCheck(PaidSign paidSign, SignChangeEvent event) {
+        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;
         }
-        return false;
+
+        performPaidSignTransaction(paidSign, player, event);
     }
 
     /**
diff --git a/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java b/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
index 0fe4086..164c9bb 100644
--- a/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
+++ b/src/main/java/net/knarcraft/paidsigns/manager/PaidSignManager.java
@@ -156,7 +156,7 @@ public final class PaidSignManager {
         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 + ".stringToMatch", condition.stringToMatch());
             conditionsSection.set(lineIndex + ".executeRegEx", condition.executeRegex());
             conditionsSection.set(lineIndex + ".ignoreCase", condition.ignoreCase());
             conditionsSection.set(lineIndex + ".ignoreColor", condition.ignoreColor());
diff --git a/src/main/java/net/knarcraft/paidsigns/manager/TrackedSignManager.java b/src/main/java/net/knarcraft/paidsigns/manager/TrackedSignManager.java
index bc78b0f..0392404 100644
--- a/src/main/java/net/knarcraft/paidsigns/manager/TrackedSignManager.java
+++ b/src/main/java/net/knarcraft/paidsigns/manager/TrackedSignManager.java
@@ -126,8 +126,8 @@ public final class TrackedSignManager {
             TrackedSign sign = trackedSigns.get(signLocation);
             String locationString = Objects.requireNonNull(signLocation.getWorld()).getUID() + "," +
                     signLocation.getBlockX() + "," + signLocation.getBlockY() + "," + signLocation.getBlockZ();
-            signSection.set(locationString + ".cost", sign.getCost());
-            signSection.set(locationString + ".playerId", sign.getPlayerId().toString());
+            signSection.set(locationString + ".cost", sign.cost());
+            signSection.set(locationString + ".playerId", sign.playerId().toString());
         }
         configuration.save(signsFile);
     }
@@ -142,8 +142,8 @@ public final class TrackedSignManager {
         if (!PaidSigns.getInstance().areRefundsEnabled() || !refund) {
             return;
         }
-        OfflinePlayer offlinePlayer = Bukkit.getOfflinePlayer(trackedSign.getPlayerId());
-        double refundSum = trackedSign.getCost() / 100 * PaidSigns.getInstance().getRefundPercentage();
+        OfflinePlayer offlinePlayer = Bukkit.getOfflinePlayer(trackedSign.playerId());
+        double refundSum = trackedSign.cost() / 100 * PaidSigns.getInstance().getRefundPercentage();
         EconomyManager.deposit(offlinePlayer, refundSum);
         if (offlinePlayer instanceof Player player) {
             player.sendMessage(String.format(StringFormatter.replacePlaceholders(