diff --git a/src/main/java/studio/magemonkey/fabled/api/util/FlagManager.java b/src/main/java/studio/magemonkey/fabled/api/util/FlagManager.java
index e4596380a8..debeba9c37 100644
--- a/src/main/java/studio/magemonkey/fabled/api/util/FlagManager.java
+++ b/src/main/java/studio/magemonkey/fabled/api/util/FlagManager.java
@@ -29,13 +29,22 @@
 import org.bukkit.entity.LivingEntity;
 
 import java.util.HashMap;
+import java.util.HashSet;
 import java.util.Map;
+import java.util.Set;
 
 /**
  * The manager for temporary entity flag data
  */
 public class FlagManager {
-    private static final Map<Integer, FlagData> data = new HashMap<>();
+    private static final Map<Integer, FlagData> data            = new HashMap<>();
+    /**
+     * Guards against reentrant clearFlags calls on the same entity.
+     * Prevents infinite recursion when FlagExpireTrigger skills add new flags
+     * during flag-clearing (e.g., on player death), which would re-create a
+     * FlagData entry and cause clearFlags → clear → removeFlag → clearFlags → ∞.
+     */
+    private static final Set<Integer>           clearingEntities = new HashSet<>();
 
     /**
      * Retrieves the flag data for an entity. This creates new data if
@@ -128,9 +137,21 @@ public static void clearFlags(LivingEntity entity) {
         if (entity == null) {
             return;
         }
-        FlagData result = data.remove(entity.getEntityId());
-        if (result != null) {
-            result.clear();
+        // Guard against reentrant calls on the same entity.
+        // FlagExpireTrigger skills may call addFlag during clearing,
+        // re-creating a FlagData entry; without this guard that would
+        // cause infinite recursion (clearFlags → clear → removeFlag → clearFlags …).
+        int id = entity.getEntityId();
+        if (!clearingEntities.add(id)) {
+            return; // already being cleared — skip
+        }
+        try {
+            FlagData result = data.remove(id);
+            if (result != null) {
+                result.clear();
+            }
+        } finally {
+            clearingEntities.remove(id);
         }
     }
 }
diff --git a/src/test/java/studio/magemonkey/fabled/api/util/FlagManagerReentrancyTest.java b/src/test/java/studio/magemonkey/fabled/api/util/FlagManagerReentrancyTest.java
new file mode 100644
index 0000000000..fcc50bc605
--- /dev/null
+++ b/src/test/java/studio/magemonkey/fabled/api/util/FlagManagerReentrancyTest.java
@@ -0,0 +1,87 @@
+package studio.magemonkey.fabled.api.util;
+
+import org.bukkit.entity.LivingEntity;
+import org.bukkit.event.EventPriority;
+import org.bukkit.event.Listener;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import studio.magemonkey.fabled.api.event.FlagExpireEvent;
+import studio.magemonkey.fabled.testutil.MockedTest;
+
+import static org.junit.jupiter.api.Assertions.assertDoesNotThrow;
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+
+/**
+ * Covers the infinite-recursion fix in FlagManager.clearFlags: a FlagExpireTrigger-driven
+ * skill can add a new flag to an entity while that entity's flags are being cleared (e.g.
+ * on death), which previously re-entered clearFlags for the same entity and recursed forever.
+ */
+public class FlagManagerReentrancyTest extends MockedTest implements Listener {
+    private LivingEntity entity;
+
+    @BeforeEach
+    void setup() {
+        entity = genPlayer("ReentrancyTester");
+    }
+
+    private void reflagOnExpire(String expiredFlag, String newFlag) {
+        server.getPluginManager().registerEvent(FlagExpireEvent.class, this, EventPriority.NORMAL,
+                (listener, event) -> {
+                    FlagExpireEvent e = (FlagExpireEvent) event;
+                    if (e.getEntity().equals(entity) && e.getFlag().equals(expiredFlag)) {
+                        FlagManager.addFlag(entity, newFlag, 100);
+                    }
+                }, plugin, true);
+    }
+
+    @Test
+    void clearFlags_reentrantAddDuringExpire_doesNotRecurseForever() {
+        reflagOnExpire("initial", "reflag");
+
+        FlagManager.addFlag(entity, "initial", 100);
+
+        assertDoesNotThrow(() -> FlagManager.clearFlags(entity));
+    }
+
+    @Test
+    void clearFlags_reentrantAdd_leavesNewlyAddedFlagIntact() {
+        reflagOnExpire("initial", "reflag");
+
+        FlagManager.addFlag(entity, "initial", 100);
+        FlagManager.clearFlags(entity);
+
+        assertFalse(FlagManager.hasFlag(entity, "initial"));
+        assertTrue(FlagManager.hasFlag(entity, "reflag"));
+    }
+
+    @Test
+    void clearFlags_selfReflagLoop_doesNotRecurseForever() {
+        // A skill that keeps re-adding the same flag on every expire would, without the
+        // guard, cause clear() -> removeFlag() -> expire event -> addFlag() -> (flags now
+        // empty again) -> clearFlags() -> clear() -> ... indefinitely for the same entity.
+        reflagOnExpire("loopy", "loopy");
+
+        FlagManager.addFlag(entity, "loopy", 100);
+
+        assertDoesNotThrow(() -> FlagManager.clearFlags(entity));
+        // The flag re-added mid-clear should survive the clear rather than being dropped.
+        assertTrue(FlagManager.hasFlag(entity, "loopy"));
+    }
+
+    @Test
+    void clearFlags_normalCase_clearsAllFlags() {
+        FlagManager.addFlag(entity, "a", 100);
+        FlagManager.addFlag(entity, "b", 100);
+
+        FlagManager.clearFlags(entity);
+
+        assertFalse(FlagManager.hasFlag(entity, "a"));
+        assertFalse(FlagManager.hasFlag(entity, "b"));
+    }
+
+    @Test
+    void clearFlags_nullEntity_doesNotThrow() {
+        assertDoesNotThrow(() -> FlagManager.clearFlags(null));
+    }
+}