diff --git a/apple/OmnivoreKit/Sources/Services/DataService/Queries/ArticleContentQuery.swift b/apple/OmnivoreKit/Sources/Services/DataService/Queries/ArticleContentQuery.swift
index 458f3be42..69ecf3686 100644
--- a/apple/OmnivoreKit/Sources/Services/DataService/Queries/ArticleContentQuery.swift
+++ b/apple/OmnivoreKit/Sources/Services/DataService/Queries/ArticleContentQuery.swift
@@ -85,9 +85,10 @@ extension DataService {
       let linkedItem = try? self.backgroundContext.fetch(fetchRequest).first
 
       if let linkedItem = linkedItem, let linkedItemID = linkedItem.id {
-        _ = highlights.map {
+        let highlightObjects = highlights.map {
           $0.asManagedObject(context: self.backgroundContext, associatedItemID: linkedItemID)
         }
+        linkedItem.addToHighlights(NSSet(array: highlightObjects))
         linkedItem.htmlContent = htmlContent
       }
 
diff --git a/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift b/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift
index 7cb9594bb..16994232b 100644
--- a/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift
+++ b/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift
@@ -15,7 +15,13 @@ struct InternalHighlight: Encodable {
   let createdByMe: Bool
 
   func asManagedObject(context: NSManagedObjectContext, associatedItemID: String) -> Highlight {
-    let highlight = Highlight(entity: Highlight.entity(), insertInto: context)
+    let fetchRequest: NSFetchRequest<Models.Highlight> = Highlight.fetchRequest()
+    fetchRequest.predicate = NSPredicate(
+      format: "id == %@", id
+    )
+    let existingHighlight = (try? context.fetch(fetchRequest))?.first
+    let highlight = existingHighlight ?? Highlight(entity: Highlight.entity(), insertInto: context)
+
     highlight.linkedItemId = associatedItemID
     highlight.markedForDeletion = false
     highlight.id = id