diff --git a/common/src/main/java/me/lucko/luckperms/common/model/NodeMap.java b/common/src/main/java/me/lucko/luckperms/common/model/NodeMap.java
index b8bcecfd..9b7248ff 100644
--- a/common/src/main/java/me/lucko/luckperms/common/model/NodeMap.java
+++ b/common/src/main/java/me/lucko/luckperms/common/model/NodeMap.java
@@ -181,9 +181,16 @@ public final class NodeMap {
         ImmutableContextSet context = node.getFullContexts().makeImmutable();
         LocalizedNode n = localise(node);
 
-        this.map.put(context, n);
-        if (node.isGroupNode() && node.getValue()) {
-            this.inheritanceMap.put(context, n);
+        SortedSet<LocalizedNode> nodesInContext = this.map.get(context);
+        nodesInContext.removeIf(e -> e.equals(node, StandardNodeEquality.IGNORE_EXPIRY_TIME_AND_VALUE));
+        nodesInContext.add(n);
+
+        if (node.isGroupNode()) {
+            SortedSet<LocalizedNode> groupNodesInContext = this.inheritanceMap.get(context);
+            groupNodesInContext.removeIf(e -> e.equals(node, StandardNodeEquality.IGNORE_EXPIRY_TIME_AND_VALUE));
+            if (node.getValue()) {
+                groupNodesInContext.add(n);
+            }
         }
     }
 
diff --git a/common/src/main/java/me/lucko/luckperms/common/model/PermissionHolder.java b/common/src/main/java/me/lucko/luckperms/common/model/PermissionHolder.java
index 5439154a..f2bc2d12 100644
--- a/common/src/main/java/me/lucko/luckperms/common/model/PermissionHolder.java
+++ b/common/src/main/java/me/lucko/luckperms/common/model/PermissionHolder.java
@@ -539,7 +539,7 @@ public abstract class PermissionHolder {
     }
 
     public DataMutateResult setPermission(Node node, boolean callEvent) {
-        if (hasPermission(NodeMapType.ENDURING, node, StandardNodeEquality.IGNORE_EXPIRY_TIME_AND_VALUE) != Tristate.UNDEFINED) {
+        if (hasPermission(NodeMapType.ENDURING, node, StandardNodeEquality.IGNORE_EXPIRY_TIME) != Tristate.UNDEFINED) {
             return DataMutateResult.ALREADY_HAS;
         }
 
@@ -565,7 +565,7 @@ public abstract class PermissionHolder {
     }
 
     public DataMutateResult setTransientPermission(Node node) {
-        if (hasPermission(NodeMapType.TRANSIENT, node, StandardNodeEquality.IGNORE_EXPIRY_TIME_AND_VALUE) != Tristate.UNDEFINED) {
+        if (hasPermission(NodeMapType.TRANSIENT, node, StandardNodeEquality.IGNORE_EXPIRY_TIME) != Tristate.UNDEFINED) {
             return DataMutateResult.ALREADY_HAS;
         }