diff --git a/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/rewards/RewardHandler.java b/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/rewards/RewardHandler.java
index 9052a2b10..64e5f5439 100644
--- a/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/rewards/RewardHandler.java
+++ b/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/rewards/RewardHandler.java
@@ -207,12 +207,12 @@ public void checkDirectlyDefinedRewardFiles() {
 
 		for (SubDirectlyDefinedReward direct : getSubDirectlyDefinedRewards()) {
 			directlyDefinedPaths.add(direct.getFullPath().replace(".", "_"));
-		}
-
-		for (Reward rewardFile : getRewards()) {
-			if (ArrayUtils.containsIgnoreCase(directlyDefinedPaths, rewardFile.getName())) {
-				plugin.getLogger().warning("Found reward file conflict: " + rewardFile.getName()
-						+ ", recommend deleting or renaming file to prevent issues");
+		}
+
+		for (Reward rewardFile : getRewards()) {
+			if (ArrayUtils.containsIgnoreCase(directlyDefinedPaths, rewardFile.getName())) {
+				plugin.getLogger().warning("Found reward file conflict: " + rewardFile.getName()
+						+ ", recommend deleting or renaming file to prevent issues");
 			}
 		}
 	}
@@ -344,13 +344,12 @@ public Reward getReward(String reward) {
 				return direct.getReward();
 			}
 		}
-
-		for (SubDirectlyDefinedReward direct : getSubDirectlyDefinedRewards()) {
-			if (direct.getFullPath().equalsIgnoreCase(reward)
-					|| direct.getFullPath().equalsIgnoreCase(reward.replaceAll("_", "."))) {
-				plugin.debug("Using subdirectlydefined reward for: " + reward);
-				return direct.getReward();
-			}
+
+		for (SubDirectlyDefinedReward direct : getSubDirectlyDefinedRewards()) {
+			if (matchesSubDirectlyDefined(direct, reward)) {
+				plugin.debug("Using subdirectlydefined reward for: " + reward);
+				return direct.getReward();
+			}
 		}
 
 		for (Reward rewardFile : getRewards()) {
@@ -450,13 +449,12 @@ public List<Reward> getRewards() {
 		return rewards;
 	}
 
-	public SubDirectlyDefinedReward getSubDirectlyDefined(String path) {
-		for (SubDirectlyDefinedReward direct : getSubDirectlyDefinedRewards()) {
-			if (direct.getFullPath().equalsIgnoreCase(path)
-					|| direct.getFullPath().equalsIgnoreCase(path.replaceAll("_", "."))) {
-				return direct;
-			}
-		}
+	public SubDirectlyDefinedReward getSubDirectlyDefined(String path) {
+		for (SubDirectlyDefinedReward direct : getSubDirectlyDefinedRewards()) {
+			if (matchesSubDirectlyDefined(direct, path)) {
+				return direct;
+			}
+		}
 		return null;
 	}
 
@@ -592,15 +590,20 @@ public boolean hasDirectRewardHandle(String reward) {
 				return true;
 			}
 		}
-
-		for (SubDirectlyDefinedReward direct : getSubDirectlyDefinedRewards()) {
-			if (direct.getFullPath().equalsIgnoreCase(reward)
-					|| direct.getFullPath().equalsIgnoreCase(reward.replaceAll("_", "."))) {
-				return true;
-			}
-		}
-		return false;
-	}
+
+		for (SubDirectlyDefinedReward direct : getSubDirectlyDefinedRewards()) {
+			if (matchesSubDirectlyDefined(direct, reward)) {
+				return true;
+			}
+		}
+		return false;
+	}
+
+	private boolean matchesSubDirectlyDefined(SubDirectlyDefinedReward direct, String reward) {
+		return direct.getFullPath().equalsIgnoreCase(reward)
+				|| direct.getFullPath().replace(".", "_").equalsIgnoreCase(reward)
+				|| direct.getFullPath().equalsIgnoreCase(reward.replaceAll("_", "."));
+	}
 
 	public boolean hasRewards(FileConfiguration data, String path) {
 		if (data.isList(path)) {
diff --git a/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/rewards/RewardHandlerTest.java b/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/rewards/RewardHandlerTest.java
new file mode 100644
index 000000000..dbd5aecba
--- /dev/null
+++ b/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/rewards/RewardHandlerTest.java
@@ -0,0 +1,80 @@
+package com.bencodez.advancedcore.tests.rewards;
+
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.when;
+
+import java.io.File;
+import java.util.logging.Logger;
+
+import org.bukkit.configuration.ConfigurationSection;
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.io.TempDir;
+
+import com.bencodez.advancedcore.AdvancedCorePlugin;
+import com.bencodez.advancedcore.api.rewards.DirectlyDefinedReward;
+import com.bencodez.advancedcore.api.rewards.RewardHandler;
+import com.bencodez.advancedcore.api.rewards.SubDirectlyDefinedReward;
+
+public class RewardHandlerTest {
+
+	@TempDir
+	File tempDir;
+
+	private RewardHandler rewardHandler;
+
+	@BeforeEach
+	public void setUp() {
+		AdvancedCorePlugin plugin = mock(AdvancedCorePlugin.class);
+		when(plugin.getDataFolder()).thenReturn(tempDir);
+		when(plugin.getLogger()).thenReturn(mock(Logger.class));
+
+		rewardHandler = new RewardHandler(plugin);
+	}
+
+	@AfterEach
+	public void tearDown() {
+		rewardHandler.getDelayedTimer().shutdownNow();
+	}
+
+	@Test
+	public void getSubDirectlyDefinedMatchesFileStylePathWithUnderscoresInParentName() {
+		rewardHandler.getSubDirectlyDefinedRewards()
+				.add(new SubDirectlyDefinedReward(directlyDefinedReward("Test_Rewards_Name"), "Rewards"));
+
+		assertNotNull(rewardHandler.getSubDirectlyDefined("Test_Rewards_Name_Rewards"));
+	}
+
+	@Test
+	public void hasDirectRewardHandleMatchesSubRewardWithUnderscoresInParentName() {
+		rewardHandler.getSubDirectlyDefinedRewards()
+				.add(new SubDirectlyDefinedReward(directlyDefinedReward("Test_Rewards_Name"), "Rewards"));
+
+		assertTrue(rewardHandler.hasDirectRewardHandle("Test_Rewards_Name_Rewards"));
+	}
+
+	private DirectlyDefinedReward directlyDefinedReward(String path) {
+		return new DirectlyDefinedReward(path) {
+
+			@Override
+			public void createSection(String key) {
+			}
+
+			@Override
+			public ConfigurationSection getFileData() {
+				return null;
+			}
+
+			@Override
+			public void save() {
+			}
+
+			@Override
+			public void setData(String path, Object value) {
+			}
+		};
+	}
+}