diff --git a/module/data/Item/attribute.mjs b/module/data/Item/attribute.mjs
index 6c83a9d..1bb65c1 100644
--- a/module/data/Item/attribute.mjs
+++ b/module/data/Item/attribute.mjs
@@ -162,7 +162,14 @@ export class AttributeItemData extends foundry.abstract.TypeDataModel {
 			});
 		};
 
-		await macro?.execute({ item: this.parent });
+		// Get the speaker so that Foundry has the correct context to be able to call
+		// the Actor's getData method, letting us augment the context dynamically for
+		// the @active roll context
+		const speaker = foundry.documents.ChatMessage.implementation.getSpeaker({
+			actor: this.parent.parent
+		});
+
+		await macro?.execute({ item: this.parent, speaker });
 	};
 	// #endregion Methods
 };
diff --git a/module/data/Item/generic.mjs b/module/data/Item/generic.mjs
index 6552f19..5c0b8db 100644
--- a/module/data/Item/generic.mjs
+++ b/module/data/Item/generic.mjs
@@ -84,6 +84,13 @@ export class GenericItemData extends foundry.abstract.TypeDataModel {
 			});
 		};
 
+		// Get the speaker so that Foundry has the correct context to be able to call
+		// the Actor's getData method, letting us augment the context dynamically for
+		// the @active roll context
+		const speaker = foundry.documents.ChatMessage.implementation.getSpeaker({
+			actor: this.parent.parent
+		});
+
 		await macro?.execute({ item: this.parent });
 	};
 	// #endregion Methods