diff --git a/src/main/java/com/sk89q/worldguard/LocalPlayer.java b/src/main/java/com/sk89q/worldguard/LocalPlayer.java
index 585acd2f..46689110 100644
--- a/src/main/java/com/sk89q/worldguard/LocalPlayer.java
+++ b/src/main/java/com/sk89q/worldguard/LocalPlayer.java
@@ -24,6 +24,7 @@
 import com.sk89q.worldguard.protection.association.RegionAssociable;
 import com.sk89q.worldguard.protection.regions.ProtectedRegion;
 
+import java.util.List;
 import java.util.UUID;
 
 public abstract class LocalPlayer implements RegionAssociable {
@@ -94,14 +95,18 @@ public abstract class LocalPlayer implements RegionAssociable {
     public abstract boolean hasPermission(String perm);
 
     @Override
-    public Association getAssociation(ProtectedRegion region) {
-        if (region.isOwner(this)) {
-            return Association.OWNER;
-        } else if (region.isMember(this)) {
-            return Association.MEMBER;
-        } else {
-            return Association.NON_MEMBER;
+    public Association getAssociation(List<ProtectedRegion> regions) {
+        boolean member = false;
+
+        for (ProtectedRegion region : regions) {
+            if (region.isOwner(this)) {
+                return Association.OWNER;
+            } else if (!member && region.isMember(this)) {
+                member = true;
+            }
         }
+
+        return member ? Association.MEMBER : Association.NON_MEMBER;
     }
 
     @Override
diff --git a/src/main/java/com/sk89q/worldguard/bukkit/protection/DelayedRegionOverlapAssociation.java b/src/main/java/com/sk89q/worldguard/bukkit/protection/DelayedRegionOverlapAssociation.java
index 953b5e69..8577639b 100644
--- a/src/main/java/com/sk89q/worldguard/bukkit/protection/DelayedRegionOverlapAssociation.java
+++ b/src/main/java/com/sk89q/worldguard/bukkit/protection/DelayedRegionOverlapAssociation.java
@@ -27,6 +27,7 @@
 import org.bukkit.Location;
 
 import javax.annotation.Nullable;
+import java.util.List;
 import java.util.Set;
 
 import static com.google.common.base.Preconditions.checkNotNull;
@@ -36,7 +37,7 @@
  * region is in a set of source regions.
  *
  * <p>This class only performs a spatial query if its
- * {@link #getAssociation(ProtectedRegion)} method is called.</p>
+ * {@link #getAssociation(List)} method is called.</p>
  */
 public class DelayedRegionOverlapAssociation implements RegionAssociable {
 
@@ -59,17 +60,19 @@ public DelayedRegionOverlapAssociation(RegionQuery query, Location location) {
     }
 
     @Override
-    public Association getAssociation(ProtectedRegion region) {
+    public Association getAssociation(List<ProtectedRegion> regions) {
         if (source == null) {
             ApplicableRegionSet result = query.getApplicableRegions(location);
             source = result.getRegions();
         }
 
-        if ((region.getId().equals(ProtectedRegion.GLOBAL_REGION) && source.isEmpty()) || source.contains(region)) {
-            return Association.OWNER;
-        } else {
-            return Association.NON_MEMBER;
+        for (ProtectedRegion region : regions) {
+            if ((region.getId().equals(ProtectedRegion.GLOBAL_REGION) && source.isEmpty()) || source.contains(region)) {
+                return Association.OWNER;
+            }
         }
+
+        return Association.NON_MEMBER;
     }
 
 }
diff --git a/src/main/java/com/sk89q/worldguard/protection/FlagValueCalculator.java b/src/main/java/com/sk89q/worldguard/protection/FlagValueCalculator.java
index 858b7e2e..b337c094 100644
--- a/src/main/java/com/sk89q/worldguard/protection/FlagValueCalculator.java
+++ b/src/main/java/com/sk89q/worldguard/protection/FlagValueCalculator.java
@@ -31,13 +31,7 @@
 import com.sk89q.worldguard.protection.regions.ProtectedRegion;
 
 import javax.annotation.Nullable;
-import java.util.Arrays;
-import java.util.Collection;
-import java.util.HashMap;
-import java.util.HashSet;
-import java.util.List;
-import java.util.Map;
-import java.util.Set;
+import java.util.*;
 
 import static com.google.common.base.Preconditions.checkNotNull;
 
@@ -157,7 +151,7 @@ public Result getMembership(RegionAssociable subject) {
             foundApplicableRegion = true;
 
             if (!hasCleared.contains(region)) {
-                if (!RegionGroup.MEMBERS.contains(subject.getAssociation(region))) {
+                if (!RegionGroup.MEMBERS.contains(subject.getAssociation(Arrays.asList(region)))) {
                     needsClear.add(region);
                 } else {
                     // Need to clear all parents
@@ -330,12 +324,6 @@ public <V> Collection<V> queryAllValues(@Nullable RegionAssociable subject, Flag
 
                     ignoreValuesOfParents(consideredValues, ignoredRegions, region);
                     consideredValues.put(region, value);
-
-                    if (value == State.DENY) {
-                        // Since DENY overrides all other values, there
-                        // is no need to consider any further regions
-                        break;
-                    }
                 }
             }
 
@@ -411,7 +399,11 @@ public <V> V getEffectiveFlag(final ProtectedRegion region, Flag<V> flag, @Nulla
 
         ProtectedRegion current = region;
 
+        List<ProtectedRegion> seen = new ArrayList<ProtectedRegion>();
+
         while (current != null) {
+            seen.add(current);
+
             V value = current.getFlag(flag);
 
             if (value != null) {
@@ -427,7 +419,7 @@ public <V> V getEffectiveFlag(final ProtectedRegion region, Flag<V> flag, @Nulla
                         use = false;
                     } else if (subject == null) {
                         use = group.contains(Association.NON_MEMBER);
-                    } else if (!group.contains(subject.getAssociation(region))) {
+                    } else if (!group.contains(subject.getAssociation(seen))) {
                         use = false;
                     }
                 }
diff --git a/src/main/java/com/sk89q/worldguard/protection/association/ConstantAssociation.java b/src/main/java/com/sk89q/worldguard/protection/association/ConstantAssociation.java
index 95e8d5e9..0f5f3a10 100644
--- a/src/main/java/com/sk89q/worldguard/protection/association/ConstantAssociation.java
+++ b/src/main/java/com/sk89q/worldguard/protection/association/ConstantAssociation.java
@@ -22,6 +22,8 @@
 import com.sk89q.worldguard.domains.Association;
 import com.sk89q.worldguard.protection.regions.ProtectedRegion;
 
+import java.util.List;
+
 class ConstantAssociation implements RegionAssociable {
 
     private final Association association;
@@ -31,7 +33,7 @@ class ConstantAssociation implements RegionAssociable {
     }
 
     @Override
-    public Association getAssociation(ProtectedRegion region) {
+    public Association getAssociation(List<ProtectedRegion> regions) {
         return association;
     }
 
diff --git a/src/main/java/com/sk89q/worldguard/protection/association/RegionAssociable.java b/src/main/java/com/sk89q/worldguard/protection/association/RegionAssociable.java
index 07e8c3f4..95b9c9f3 100644
--- a/src/main/java/com/sk89q/worldguard/protection/association/RegionAssociable.java
+++ b/src/main/java/com/sk89q/worldguard/protection/association/RegionAssociable.java
@@ -22,17 +22,19 @@
 import com.sk89q.worldguard.domains.Association;
 import com.sk89q.worldguard.protection.regions.ProtectedRegion;
 
+import java.util.List;
+
 /**
  * An object that can have membership in a region.
  */
 public interface RegionAssociable {
 
     /**
-     * Get the most specific association level for the input region.
+     * Get the highest association level for the input regions.
      *
-     * @param region the input region
-     * @return the most specific membership level
+     * @param regions a list of regions
+     * @return the highest membership level
      */
-    Association getAssociation(ProtectedRegion region);
+    Association getAssociation(List<ProtectedRegion> regions);
 
 }
diff --git a/src/main/java/com/sk89q/worldguard/protection/association/RegionOverlapAssociation.java b/src/main/java/com/sk89q/worldguard/protection/association/RegionOverlapAssociation.java
index 7165c9c2..0c7cdef2 100644
--- a/src/main/java/com/sk89q/worldguard/protection/association/RegionOverlapAssociation.java
+++ b/src/main/java/com/sk89q/worldguard/protection/association/RegionOverlapAssociation.java
@@ -22,6 +22,7 @@
 import com.sk89q.worldguard.domains.Association;
 import com.sk89q.worldguard.protection.regions.ProtectedRegion;
 
+import java.util.List;
 import java.util.Set;
 
 import static com.google.common.base.Preconditions.checkNotNull;
@@ -45,12 +46,14 @@ public RegionOverlapAssociation(Set<ProtectedRegion> source) {
     }
 
     @Override
-    public Association getAssociation(ProtectedRegion region) {
-        if (source.contains(region)) {
-            return Association.OWNER;
-        } else {
-            return Association.NON_MEMBER;
+    public Association getAssociation(List<ProtectedRegion> regions) {
+        for (ProtectedRegion region : regions) {
+            if (source.contains(region)) {
+                return Association.OWNER;
+            }
         }
+
+        return Association.NON_MEMBER;
     }
 
 }