diff --git a/pymongo/results.py b/pymongo/results.py
index b34f6c4926..d17ff1c3ea 100644
--- a/pymongo/results.py
+++ b/pymongo/results.py
@@ -171,9 +171,12 @@ def upserted_id(self) -> Any:
 
     @property
     def did_upsert(self) -> bool:
-        """Whether or not an upsert took place."""
+        """Whether an upsert took place.
+
+        .. versionadded:: 4.9
+        """
         assert self.__raw_result is not None
-        return len(self.__raw_result.get("upserted", {})) > 0
+        return "upserted" in self.__raw_result
 
 
 class DeleteResult(_WriteResult):
diff --git a/test/asynchronous/test_client_bulk_write.py b/test/asynchronous/test_client_bulk_write.py
index 80cfd30bde..9464337809 100644
--- a/test/asynchronous/test_client_bulk_write.py
+++ b/test/asynchronous/test_client_bulk_write.py
@@ -550,6 +550,46 @@ async def test_returns_error_if_auto_encryption_configured(self):
             "bulk_write does not currently support automatic encryption", context.exception._message
         )
 
+    @async_client_context.require_version_min(8, 0, 0, -24)
+    @async_client_context.require_no_serverless
+    async def test_upserted_result(self):
+        client = await self.async_rs_or_single_client()
+
+        collection = client.db["coll"]
+        self.addAsyncCleanup(collection.drop)
+        await collection.drop()
+
+        models = []
+        models.append(
+            UpdateOne(
+                namespace="db.coll",
+                filter={"_id": "a"},
+                update={"$set": {"x": 1}},
+                upsert=True,
+            )
+        )
+        models.append(
+            UpdateOne(
+                namespace="db.coll",
+                filter={"_id": None},
+                update={"$set": {"x": 1}},
+                upsert=True,
+            )
+        )
+        models.append(
+            UpdateOne(
+                namespace="db.coll",
+                filter={"_id": None},
+                update={"$set": {"x": 1}},
+            )
+        )
+        result = await client.bulk_write(models=models, verbose_results=True)
+
+        self.assertEqual(result.upserted_count, 2)
+        self.assertEqual(result.update_results[0].did_upsert, True)
+        self.assertEqual(result.update_results[1].did_upsert, True)
+        self.assertEqual(result.update_results[2].did_upsert, False)
+
 
 # https://github.com/mongodb/specifications/blob/master/source/client-side-operations-timeout/tests/README.md#11-multi-batch-bulkwrites
 class TestClientBulkWriteCSOT(AsyncIntegrationTest):
diff --git a/test/asynchronous/test_collection.py b/test/asynchronous/test_collection.py
index 74a4a5151d..612090b69f 100644
--- a/test/asynchronous/test_collection.py
+++ b/test/asynchronous/test_collection.py
@@ -1444,6 +1444,19 @@ async def test_update_one(self):
         self.assertRaises(InvalidOperation, lambda: result.upserted_id)
         self.assertFalse(result.acknowledged)
 
+    async def test_update_result(self):
+        db = self.db
+        await db.drop_collection("test")
+
+        result = await db.test.update_one({"x": 0}, {"$inc": {"x": 1}}, upsert=True)
+        self.assertEqual(result.did_upsert, True)
+
+        result = await db.test.update_one({"_id": None, "x": 0}, {"$inc": {"x": 1}}, upsert=True)
+        self.assertEqual(result.did_upsert, True)
+
+        result = await db.test.update_one({"_id": None}, {"$inc": {"x": 1}})
+        self.assertEqual(result.did_upsert, False)
+
     async def test_update_many(self):
         db = self.db
         await db.drop_collection("test")
diff --git a/test/test_client_bulk_write.py b/test/test_client_bulk_write.py
index d1aff03fc9..58b5015dd2 100644
--- a/test/test_client_bulk_write.py
+++ b/test/test_client_bulk_write.py
@@ -550,6 +550,46 @@ def test_returns_error_if_auto_encryption_configured(self):
             "bulk_write does not currently support automatic encryption", context.exception._message
         )
 
+    @client_context.require_version_min(8, 0, 0, -24)
+    @client_context.require_no_serverless
+    def test_upserted_result(self):
+        client = self.rs_or_single_client()
+
+        collection = client.db["coll"]
+        self.addCleanup(collection.drop)
+        collection.drop()
+
+        models = []
+        models.append(
+            UpdateOne(
+                namespace="db.coll",
+                filter={"_id": "a"},
+                update={"$set": {"x": 1}},
+                upsert=True,
+            )
+        )
+        models.append(
+            UpdateOne(
+                namespace="db.coll",
+                filter={"_id": None},
+                update={"$set": {"x": 1}},
+                upsert=True,
+            )
+        )
+        models.append(
+            UpdateOne(
+                namespace="db.coll",
+                filter={"_id": None},
+                update={"$set": {"x": 1}},
+            )
+        )
+        result = client.bulk_write(models=models, verbose_results=True)
+
+        self.assertEqual(result.upserted_count, 2)
+        self.assertEqual(result.update_results[0].did_upsert, True)
+        self.assertEqual(result.update_results[1].did_upsert, True)
+        self.assertEqual(result.update_results[2].did_upsert, False)
+
 
 # https://github.com/mongodb/specifications/blob/master/source/client-side-operations-timeout/tests/README.md#11-multi-batch-bulkwrites
 class TestClientBulkWriteCSOT(IntegrationTest):
diff --git a/test/test_collection.py b/test/test_collection.py
index dab59cf1b2..a2c3b0b0b6 100644
--- a/test/test_collection.py
+++ b/test/test_collection.py
@@ -1429,6 +1429,19 @@ def test_update_one(self):
         self.assertRaises(InvalidOperation, lambda: result.upserted_id)
         self.assertFalse(result.acknowledged)
 
+    def test_update_result(self):
+        db = self.db
+        db.drop_collection("test")
+
+        result = db.test.update_one({"x": 0}, {"$inc": {"x": 1}}, upsert=True)
+        self.assertEqual(result.did_upsert, True)
+
+        result = db.test.update_one({"_id": None, "x": 0}, {"$inc": {"x": 1}}, upsert=True)
+        self.assertEqual(result.did_upsert, True)
+
+        result = db.test.update_one({"_id": None}, {"$inc": {"x": 1}})
+        self.assertEqual(result.did_upsert, False)
+
     def test_update_many(self):
         db = self.db
         db.drop_collection("test")
diff --git a/test/test_results.py b/test/test_results.py
index 19e086a9a5..deb09d7ed4 100644
--- a/test/test_results.py
+++ b/test/test_results.py
@@ -122,6 +122,28 @@ def test_update_result(self):
         self.assertEqual(raw_result["n"], result.matched_count)
         self.assertEqual(raw_result["nModified"], result.modified_count)
         self.assertEqual(raw_result["upserted"], result.upserted_id)
+        self.assertEqual(result.did_upsert, True)
+
+        raw_result_2 = {
+            "n": 1,
+            "nModified": 1,
+            "upserted": [
+                {"index": 5, "_id": 1},
+            ],
+        }
+        self.repr_test(UpdateResult, raw_result_2)
+
+        result = UpdateResult(raw_result_2, True)
+        self.assertEqual(result.did_upsert, True)
+
+        raw_result_3 = {
+            "n": 1,
+            "nModified": 1,
+        }
+        self.repr_test(UpdateResult, raw_result_3)
+
+        result = UpdateResult(raw_result_3, True)
+        self.assertEqual(result.did_upsert, False)
 
         result = UpdateResult(raw_result, False)
         self.assertEqual(raw_result, result.raw_result)