diff --git a/apple/OmnivoreKit/Sources/Models/CoreData/CoreDataModel.xcdatamodeld/CoreDataModel.xcdatamodel/contents b/apple/OmnivoreKit/Sources/Models/CoreData/CoreDataModel.xcdatamodeld/CoreDataModel.xcdatamodel/contents
index cbd574d78..b46bf97e7 100644
--- a/apple/OmnivoreKit/Sources/Models/CoreData/CoreDataModel.xcdatamodeld/CoreDataModel.xcdatamodel/contents
+++ b/apple/OmnivoreKit/Sources/Models/CoreData/CoreDataModel.xcdatamodeld/CoreDataModel.xcdatamodel/contents
@@ -13,6 +13,7 @@
         <attribute name="shortId" attributeType="String"/>
         <attribute name="suffix" optional="YES" attributeType="String"/>
         <attribute name="updatedAt" optional="YES" attributeType="Date" usesScalarValueType="NO"/>
+        <relationship name="labels" optional="YES" toMany="YES" deletionRule="Nullify" destinationEntity="LinkedItemLabel" inverseName="highlight" inverseEntity="LinkedItemLabel"/>
         <relationship name="linkedItem" optional="YES" maxCount="1" deletionRule="Nullify" destinationEntity="LinkedItem" inverseName="highlights" inverseEntity="LinkedItem"/>
         <uniquenessConstraints>
             <uniquenessConstraint>
@@ -67,6 +68,7 @@
         <attribute name="labelDescription" optional="YES" attributeType="String"/>
         <attribute name="name" attributeType="String"/>
         <attribute name="serverSyncStatus" attributeType="Integer 64" defaultValueString="NO" usesScalarValueType="YES"/>
+        <relationship name="highlight" optional="YES" maxCount="1" deletionRule="Nullify" destinationEntity="Highlight" inverseName="labels" inverseEntity="Highlight"/>
         <relationship name="linkedItems" optional="YES" toMany="YES" deletionRule="Nullify" destinationEntity="LinkedItem" inverseName="labels" inverseEntity="LinkedItem"/>
         <uniquenessConstraints>
             <uniquenessConstraint>
diff --git a/apple/OmnivoreKit/Sources/Services/DataService/Mutations/CreateHighlight.swift b/apple/OmnivoreKit/Sources/Services/DataService/Mutations/CreateHighlight.swift
index 5cd1ad36d..66878c579 100644
--- a/apple/OmnivoreKit/Sources/Services/DataService/Mutations/CreateHighlight.swift
+++ b/apple/OmnivoreKit/Sources/Services/DataService/Mutations/CreateHighlight.swift
@@ -21,7 +21,8 @@ extension DataService {
       annotation: annotation,
       createdAt: nil,
       updatedAt: nil,
-      createdByMe: true
+      createdByMe: true,
+      labels: []
     )
 
     internalHighlight.persist(context: backgroundContext, associatedItemID: articleId)
diff --git a/apple/OmnivoreKit/Sources/Services/DataService/Mutations/MergeHighlight.swift b/apple/OmnivoreKit/Sources/Services/DataService/Mutations/MergeHighlight.swift
index cb3e2c0d5..cdf78dc58 100644
--- a/apple/OmnivoreKit/Sources/Services/DataService/Mutations/MergeHighlight.swift
+++ b/apple/OmnivoreKit/Sources/Services/DataService/Mutations/MergeHighlight.swift
@@ -23,7 +23,8 @@ extension DataService {
       annotation: nil,
       createdAt: nil,
       updatedAt: nil,
-      createdByMe: true
+      createdByMe: true,
+      labels: []
     )
 
     internalHighlight.persist(
diff --git a/apple/OmnivoreKit/Sources/Services/DataService/Selections/HighlightSelection.swift b/apple/OmnivoreKit/Sources/Services/DataService/Selections/HighlightSelection.swift
index 173dfe020..5deb56277 100644
--- a/apple/OmnivoreKit/Sources/Services/DataService/Selections/HighlightSelection.swift
+++ b/apple/OmnivoreKit/Sources/Services/DataService/Selections/HighlightSelection.swift
@@ -1,6 +1,16 @@
 import Models
 import SwiftGraphQL
 
+let highlightLabelSelection = Selection.Label {
+  InternalLinkedItemLabel(
+    id: try $0.id(),
+    name: try $0.name(),
+    color: try $0.color(),
+    createdAt: try $0.createdAt()?.value,
+    labelDescription: try $0.description()
+  )
+}
+
 let highlightSelection = Selection.Highlight {
   InternalHighlight(
     id: try $0.id(),
@@ -12,6 +22,7 @@ let highlightSelection = Selection.Highlight {
     annotation: try $0.annotation(),
     createdAt: try $0.createdAt().value,
     updatedAt: try $0.updatedAt().value,
-    createdByMe: try $0.createdByMe()
+    createdByMe: try $0.createdByMe(),
+    labels: try $0.labels(selection: highlightLabelSelection.list.nullable) ?? []
   )
 }
diff --git a/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift b/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift
index 450d5e759..e1640bcb8 100644
--- a/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift
+++ b/apple/OmnivoreKit/Sources/Services/InternalModels/InternalHighlight.swift
@@ -13,6 +13,7 @@ struct InternalHighlight: Encodable {
   let createdAt: Date?
   let updatedAt: Date?
   let createdByMe: Bool
+  var labels: [InternalLinkedItemLabel]
 
   func asManagedObject(context: NSManagedObjectContext) -> Highlight {
     let fetchRequest: NSFetchRequest<Models.Highlight> = Highlight.fetchRequest()
@@ -33,6 +34,15 @@ struct InternalHighlight: Encodable {
     highlight.createdAt = createdAt
     highlight.updatedAt = updatedAt
     highlight.createdByMe = createdByMe
+
+    if let existingLabels = highlight.labels {
+      highlight.removeFromLabels(existingLabels)
+    }
+
+    for label in labels {
+      highlight.addToLabels(label.asManagedObject(inContext: context))
+    }
+
     return highlight
   }
 
@@ -47,7 +57,8 @@ struct InternalHighlight: Encodable {
       annotation: highlight.annotation,
       createdAt: highlight.createdAt,
       updatedAt: highlight.updatedAt,
-      createdByMe: highlight.createdByMe
+      createdByMe: highlight.createdByMe,
+      labels: InternalLinkedItemLabel.make(highlight.labels)
     )
   }
 
diff --git a/apple/OmnivoreKit/Sources/Services/InternalModels/InternalLinkedItemLabel.swift b/apple/OmnivoreKit/Sources/Services/InternalModels/InternalLinkedItemLabel.swift
index d6707c7b1..301f341a0 100644
--- a/apple/OmnivoreKit/Sources/Services/InternalModels/InternalLinkedItemLabel.swift
+++ b/apple/OmnivoreKit/Sources/Services/InternalModels/InternalLinkedItemLabel.swift
@@ -2,7 +2,7 @@ import CoreData
 import Foundation
 import Models
 
-struct InternalLinkedItemLabel {
+struct InternalLinkedItemLabel: Encodable {
   let id: String
   let name: String
   let color: String
@@ -38,6 +38,22 @@ struct InternalLinkedItemLabel {
     label.labelDescription = labelDescription
     return label
   }
+
+  static func make(_ labels: NSSet?) -> [InternalLinkedItemLabel] {
+    labels?
+      .compactMap { label in
+        if let label = label as? LinkedItemLabel {
+          return InternalLinkedItemLabel(
+            id: label.id ?? "",
+            name: label.name ?? "",
+            color: label.color ?? "",
+            createdAt: label.createdAt,
+            labelDescription: label.labelDescription
+          )
+        }
+        return nil
+      } ?? []
+  }
 }
 
 extension LinkedItemLabel {