diff --git a/Maccy/Observables/History.swift b/Maccy/Observables/History.swift
index e5804ad19..53487b8f7 100644
--- a/Maccy/Observables/History.swift
+++ b/Maccy/Observables/History.swift
@@ -146,7 +146,11 @@ class History: ItemsContainer { // swiftlint:disable:this type_body_length
     var removedItemIndex: Int?
     if let existingHistoryItem = findSimilarItem(item) {
       if isModified(item) == nil {
+        for content in item.contents {
+          Storage.shared.context.delete(content)
+        }
         item.contents = existingHistoryItem.contents
+        existingHistoryItem.contents = []
       }
       item.firstCopiedAt = existingHistoryItem.firstCopiedAt
       item.numberOfCopies += existingHistoryItem.numberOfCopies
diff --git a/MaccyTests/HistoryTests.swift b/MaccyTests/HistoryTests.swift
index a6d4be983..e072fe32d 100644
--- a/MaccyTests/HistoryTests.swift
+++ b/MaccyTests/HistoryTests.swift
@@ -1,5 +1,6 @@
 import XCTest
 import Defaults
+import SwiftData
 @testable import Maccy
 
 @MainActor
@@ -123,6 +124,23 @@ class HistoryTests: XCTestCase {
     XCTAssertEqual(Set(history.items[0].item.contents), Set(firstContents))
   }
 
+  func testDuplicateDoesNotOrphanContents() {
+    let item = historyItem("foo")
+    history.add(item)
+
+    let descriptor1 = FetchDescriptor<HistoryItemContent>()
+    let contents1 = try? Storage.shared.context.fetch(descriptor1)
+    XCTAssertEqual(contents1?.count, 1)
+
+    let duplicate = historyItem("foo")
+    history.add(duplicate)
+
+    let descriptor2 = FetchDescriptor<HistoryItemContent>()
+    let contents2 = try? Storage.shared.context.fetch(descriptor2)
+    XCTAssertEqual(contents2?.count, 1)
+    XCTAssertNotNil(contents2?.first?.item)
+  }
+
   func testAddingItemFromMaccy() {
     let firstContents = [
       HistoryItemContent(