diff --git a/module/documents/item.mjs b/module/documents/item.mjs
index 35b9e32f..68602db5 100644
--- a/module/documents/item.mjs
+++ b/module/documents/item.mjs
@@ -9,6 +9,46 @@ export default class DHItem extends foundry.documents.Item {
         for (const action of this.system.actions ?? []) action.prepareData();
     }
 
+    /**
+     * @inheritdoc
+     */
+    async _preUpdate(changed, options, user) {
+        const result = await super._preUpdate(changed, options, user);
+        
+        // Store the previous equipped status for attachment handling
+        if (changed.system?.equipped !== undefined) {
+            options.previousEquipped = this.system.equipped;
+        }
+        
+        return result;
+    }
+
+    /**
+     * @inheritdoc
+     */
+    async _onUpdate(changed, options, user) {
+        await super._onUpdate(changed, options, user);
+        
+        // Handle attachment effects when equipped status changes
+        if (changed.system?.equipped !== undefined && options.previousEquipped !== changed.system.equipped) {
+            const newEquippedStatus = changed.system.equipped;
+            const parentType = this.type === 'armor' ? 'armor' : this.type === 'weapon' ? 'weapon' : null;
+            
+            if (parentType) {
+                try {
+                    const { handleAttachmentEffectsOnEquipChange } = await import('../helpers/attachmentHelper.mjs');
+                    await handleAttachmentEffectsOnEquipChange({
+                        parentItem: this,
+                        newEquippedStatus,
+                        parentType
+                    });
+                } catch (error) {
+                    console.error('DH | Error in handleAttachmentEffectsOnEquipChange:', error);
+                }
+            }
+        }
+    }
+
     /**
      * @inheritdoc
      * @param {object} options - Options which modify the getRollData method.
diff --git a/module/helpers/attachmentHelper.mjs b/module/helpers/attachmentHelper.mjs
index 0e209881..c456d2e4 100644
--- a/module/helpers/attachmentHelper.mjs
+++ b/module/helpers/attachmentHelper.mjs
@@ -105,22 +105,24 @@ export async function removeAttachmentFromItem({ parentItem, attachedUuid, paren
  * @returns {Promise<void>}
  */
 export async function handleAttachmentEffectsOnEquipChange({ parentItem, newEquippedStatus, parentType }) {
-    const actor = parentItem.parent?.parent;
-    if (!actor || !parentItem.system.attached?.length) return;
+    // Try to get the actor - it might be parentItem.parent instead of parentItem.parent.parent
+    const actor = parentItem.parent?.type === 'character' ? parentItem.parent : parentItem.parent?.parent;
+    
+    if (!actor || !parentItem.system.attached?.length) {
+        return;
+    }
 
     if (newEquippedStatus) {
         // Item is being equipped - add attachment effects
-        const effectsToCreate = [];
         for (const attachedUuid of parentItem.system.attached) {
             const attachedItem = await fromUuid(attachedUuid);
             if (attachedItem && attachedItem.effects.size > 0) {
-                const newEffects = await copyAttachmentEffectsToActor({
+                await copyAttachmentEffectsToActor({
                     parentItem,
                     attachedItem,
                     attachedUuid,
                     parentType
                 });
-                effectsToCreate.push(...newEffects);
             }
         }
     } else {