diff --git a/src/EFCore.Relational/Query/SqlExpressions/SelectExpression.cs b/src/EFCore.Relational/Query/SqlExpressions/SelectExpression.cs
index b510c493bd2..c07ef8d2c48 100644
--- a/src/EFCore.Relational/Query/SqlExpressions/SelectExpression.cs
+++ b/src/EFCore.Relational/Query/SqlExpressions/SelectExpression.cs
@@ -920,8 +920,8 @@ static Expression RemoveConvert(Expression expression)
                             var actualParentIdentifier = _identifier.Take(outerSelectExpression._identifier.Count).ToList();
                             for (var j = 0; j < actualParentIdentifier.Count; j++)
                             {
-                                AppendOrdering(new OrderingExpression(actualParentIdentifier[j].Column, ascending: true));
-                                outerSelectExpression.AppendOrdering(
+                                AppendOrderingInternal(new OrderingExpression(actualParentIdentifier[j].Column, ascending: true));
+                                outerSelectExpression.AppendOrderingInternal(
                                     new OrderingExpression(outerSelectExpression._identifier[j].Column, ascending: true));
                             }
 
@@ -1860,6 +1860,11 @@ private static void PopulateGroupByTerms(
     /// <param name="orderingExpression">An ordering expression to use for ordering.</param>
     public void ApplyOrdering(OrderingExpression orderingExpression)
     {
+        if (Limit is SqlConstantExpression { Value: 1 })
+        {
+            return;
+        }
+
         if (IsDistinct
             || Limit != null
             || Offset != null)
@@ -1877,14 +1882,21 @@ public void ApplyOrdering(OrderingExpression orderingExpression)
     /// <param name="orderingExpression">An ordering expression to use for ordering.</param>
     public void AppendOrdering(OrderingExpression orderingExpression)
     {
-        if (!_orderings.Any(o => o.Expression.Equals(orderingExpression.Expression)))
+        if (Limit is SqlConstantExpression { Value: 1 })
         {
-            AppendOrderingInternal(orderingExpression);
+            return;
         }
+
+        AppendOrderingInternal(orderingExpression);
     }
 
     private void AppendOrderingInternal(OrderingExpression orderingExpression)
-        => _orderings.Add(orderingExpression.Update(orderingExpression.Expression));
+    {
+        if (!_orderings.Any(o => o.Expression.Equals(orderingExpression.Expression)))
+        {
+            _orderings.Add(orderingExpression);
+        }
+    }
 
     /// <summary>
     ///     Reverses the existing orderings on the <see cref="SelectExpression" />.
diff --git a/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindSelectQueryCosmosTest.cs b/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindSelectQueryCosmosTest.cs
index b05fbdf7475..1729032d122 100644
--- a/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindSelectQueryCosmosTest.cs
+++ b/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindSelectQueryCosmosTest.cs
@@ -722,6 +722,15 @@ public override async Task Project_single_element_from_collection_with_OrderBy_T
         AssertSql();
     }
 
+    public override async Task Project_single_element_from_collection_with_OrderBy_Take_OrderBy_and_FirstOrDefault(bool async)
+    {
+        // Cosmos client evaluation. Issue #17246.
+        await AssertTranslationFailed(
+            () => base.Project_single_element_from_collection_with_OrderBy_Take_OrderBy_and_FirstOrDefault(async));
+
+        AssertSql();
+    }
+
     public override async Task Project_single_element_from_collection_with_OrderBy_Take_and_FirstOrDefault_with_parameter(bool async)
     {
         // Cosmos client evaluation. Issue #17246.
diff --git a/test/EFCore.Specification.Tests/Query/NorthwindSelectQueryTestBase.cs b/test/EFCore.Specification.Tests/Query/NorthwindSelectQueryTestBase.cs
index cbd036ad513..83c1812aaee 100644
--- a/test/EFCore.Specification.Tests/Query/NorthwindSelectQueryTestBase.cs
+++ b/test/EFCore.Specification.Tests/Query/NorthwindSelectQueryTestBase.cs
@@ -1017,6 +1017,14 @@ public virtual Task Project_single_element_from_collection_with_OrderBy_Take_and
             async,
             ss => ss.Set<Customer>().Select(c => c.Orders.OrderBy(o => o.OrderID).Select(o => o.CustomerID).Take(1).FirstOrDefault()));
 
+    [ConditionalTheory]
+    [MemberData(nameof(IsAsyncData))]
+    public virtual Task Project_single_element_from_collection_with_OrderBy_Take_OrderBy_and_FirstOrDefault(bool async)
+        => AssertQuery(
+            async,
+            ss => ss.Set<Customer>().Select(
+                c => c.Orders.OrderBy(o => o.OrderID).Take(1).OrderBy(o => o.OrderDate).FirstOrDefault()));
+
     [ConditionalTheory]
     [MemberData(nameof(IsAsyncData))]
     public virtual Task Project_single_element_from_collection_with_OrderBy_Skip_and_FirstOrDefault(bool async)
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServer160Test.cs b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServer160Test.cs
index 69f02149536..95aac4827b3 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServer160Test.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServer160Test.cs
@@ -67,12 +67,8 @@ where l1.Id < 3
         AssertSql(
             """
 SELECT (
-    SELECT TOP(1) [l1].[Name]
-    FROM (
-        SELECT TOP(1) [l0].[Id], [l0].[Name]
-        FROM [LevelThree] AS [l0]
-    ) AS [l1]
-    ORDER BY [l1].[Id])
+    SELECT TOP(1) [l0].[Name]
+    FROM [LevelThree] AS [l0])
 FROM [LevelOne] AS [l]
 WHERE [l].[Id] < 3
 """);
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServerTest.cs b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServerTest.cs
index 16b4f166b45..92465352e8e 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServerTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsQuerySqlServerTest.cs
@@ -67,12 +67,8 @@ where l1.Id < 3
         AssertSql(
             """
 SELECT (
-    SELECT TOP(1) [l1].[Name]
-    FROM (
-        SELECT TOP(1) [l0].[Id], [l0].[Name]
-        FROM [LevelThree] AS [l0]
-    ) AS [l1]
-    ORDER BY [l1].[Id])
+    SELECT TOP(1) [l0].[Name]
+    FROM [LevelThree] AS [l0])
 FROM [LevelOne] AS [l]
 WHERE [l].[Id] < 3
 """);
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServer160Test.cs b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServer160Test.cs
index 075eaf6fffa..31de2a01c62 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServer160Test.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServer160Test.cs
@@ -85,31 +85,25 @@ where l1.Id < 3
         AssertSql(
             """
 SELECT (
-    SELECT TOP(1) [s].[Level3_Name]
-    FROM (
-        SELECT TOP(1) [l4].[Id], [l4].[Level2_Required_Id], [l4].[Level3_Name], [l4].[OneToMany_Required_Inverse3Id]
-        FROM [Level1] AS [l0]
-        LEFT JOIN (
-            SELECT [l1].[Id], [l1].[OneToOne_Required_PK_Date], [l1].[Level1_Required_Id], [l1].[OneToMany_Required_Inverse2Id]
-            FROM [Level1] AS [l1]
-            WHERE [l1].[OneToOne_Required_PK_Date] IS NOT NULL AND [l1].[Level1_Required_Id] IS NOT NULL AND [l1].[OneToMany_Required_Inverse2Id] IS NOT NULL
-        ) AS [l2] ON [l0].[Id] = CASE
-            WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
-        END
-        LEFT JOIN (
-            SELECT [l3].[Id], [l3].[Level2_Required_Id], [l3].[Level3_Name], [l3].[OneToMany_Required_Inverse3Id]
-            FROM [Level1] AS [l3]
-            WHERE [l3].[Level2_Required_Id] IS NOT NULL AND [l3].[OneToMany_Required_Inverse3Id] IS NOT NULL
-        ) AS [l4] ON CASE
-            WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
-        END = CASE
-            WHEN [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL THEN [l4].[Id]
-        END
-        WHERE [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL AND [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL
-    ) AS [s]
-    ORDER BY CASE
-        WHEN [s].[Level2_Required_Id] IS NOT NULL AND [s].[OneToMany_Required_Inverse3Id] IS NOT NULL THEN [s].[Id]
-    END)
+    SELECT TOP(1) [l4].[Level3_Name]
+    FROM [Level1] AS [l0]
+    LEFT JOIN (
+        SELECT [l1].[Id], [l1].[OneToOne_Required_PK_Date], [l1].[Level1_Required_Id], [l1].[OneToMany_Required_Inverse2Id]
+        FROM [Level1] AS [l1]
+        WHERE [l1].[OneToOne_Required_PK_Date] IS NOT NULL AND [l1].[Level1_Required_Id] IS NOT NULL AND [l1].[OneToMany_Required_Inverse2Id] IS NOT NULL
+    ) AS [l2] ON [l0].[Id] = CASE
+        WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
+    END
+    LEFT JOIN (
+        SELECT [l3].[Id], [l3].[Level2_Required_Id], [l3].[Level3_Name], [l3].[OneToMany_Required_Inverse3Id]
+        FROM [Level1] AS [l3]
+        WHERE [l3].[Level2_Required_Id] IS NOT NULL AND [l3].[OneToMany_Required_Inverse3Id] IS NOT NULL
+    ) AS [l4] ON CASE
+        WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
+    END = CASE
+        WHEN [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL THEN [l4].[Id]
+    END
+    WHERE [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL AND [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL)
 FROM [Level1] AS [l]
 WHERE [l].[Id] < 3
 """);
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServerTest.cs b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServerTest.cs
index c6edb779d49..c2686849f93 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServerTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/ComplexNavigationsSharedTypeQuerySqlServerTest.cs
@@ -87,31 +87,25 @@ where l1.Id < 3
         AssertSql(
             """
 SELECT (
-    SELECT TOP(1) [s].[Level3_Name]
-    FROM (
-        SELECT TOP(1) [l4].[Id], [l4].[Level2_Required_Id], [l4].[Level3_Name], [l4].[OneToMany_Required_Inverse3Id]
-        FROM [Level1] AS [l0]
-        LEFT JOIN (
-            SELECT [l1].[Id], [l1].[OneToOne_Required_PK_Date], [l1].[Level1_Required_Id], [l1].[OneToMany_Required_Inverse2Id]
-            FROM [Level1] AS [l1]
-            WHERE [l1].[OneToOne_Required_PK_Date] IS NOT NULL AND [l1].[Level1_Required_Id] IS NOT NULL AND [l1].[OneToMany_Required_Inverse2Id] IS NOT NULL
-        ) AS [l2] ON [l0].[Id] = CASE
-            WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
-        END
-        LEFT JOIN (
-            SELECT [l3].[Id], [l3].[Level2_Required_Id], [l3].[Level3_Name], [l3].[OneToMany_Required_Inverse3Id]
-            FROM [Level1] AS [l3]
-            WHERE [l3].[Level2_Required_Id] IS NOT NULL AND [l3].[OneToMany_Required_Inverse3Id] IS NOT NULL
-        ) AS [l4] ON CASE
-            WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
-        END = CASE
-            WHEN [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL THEN [l4].[Id]
-        END
-        WHERE [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL AND [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL
-    ) AS [s]
-    ORDER BY CASE
-        WHEN [s].[Level2_Required_Id] IS NOT NULL AND [s].[OneToMany_Required_Inverse3Id] IS NOT NULL THEN [s].[Id]
-    END)
+    SELECT TOP(1) [l4].[Level3_Name]
+    FROM [Level1] AS [l0]
+    LEFT JOIN (
+        SELECT [l1].[Id], [l1].[OneToOne_Required_PK_Date], [l1].[Level1_Required_Id], [l1].[OneToMany_Required_Inverse2Id]
+        FROM [Level1] AS [l1]
+        WHERE [l1].[OneToOne_Required_PK_Date] IS NOT NULL AND [l1].[Level1_Required_Id] IS NOT NULL AND [l1].[OneToMany_Required_Inverse2Id] IS NOT NULL
+    ) AS [l2] ON [l0].[Id] = CASE
+        WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
+    END
+    LEFT JOIN (
+        SELECT [l3].[Id], [l3].[Level2_Required_Id], [l3].[Level3_Name], [l3].[OneToMany_Required_Inverse3Id]
+        FROM [Level1] AS [l3]
+        WHERE [l3].[Level2_Required_Id] IS NOT NULL AND [l3].[OneToMany_Required_Inverse3Id] IS NOT NULL
+    ) AS [l4] ON CASE
+        WHEN [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL THEN [l2].[Id]
+    END = CASE
+        WHEN [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL THEN [l4].[Id]
+    END
+    WHERE [l2].[OneToOne_Required_PK_Date] IS NOT NULL AND [l2].[Level1_Required_Id] IS NOT NULL AND [l2].[OneToMany_Required_Inverse2Id] IS NOT NULL AND [l4].[Level2_Required_Id] IS NOT NULL AND [l4].[OneToMany_Required_Inverse3Id] IS NOT NULL)
 FROM [Level1] AS [l]
 WHERE [l].[Id] < 3
 """);
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindSelectQuerySqlServerTest.cs b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindSelectQuerySqlServerTest.cs
index 922fa23af79..acfa05fe027 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindSelectQuerySqlServerTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindSelectQuerySqlServerTest.cs
@@ -768,6 +768,25 @@ FROM [Customers] AS [c]
 """);
     }
 
+    public override async Task Project_single_element_from_collection_with_OrderBy_Take_OrderBy_and_FirstOrDefault(bool async)
+    {
+        await base.Project_single_element_from_collection_with_OrderBy_Take_OrderBy_and_FirstOrDefault(async);
+
+        AssertSql(
+            """
+SELECT [o1].[OrderID], [o1].[CustomerID], [o1].[EmployeeID], [o1].[OrderDate]
+FROM [Customers] AS [c]
+LEFT JOIN (
+    SELECT [o0].[OrderID], [o0].[CustomerID], [o0].[EmployeeID], [o0].[OrderDate]
+    FROM (
+        SELECT [o].[OrderID], [o].[CustomerID], [o].[EmployeeID], [o].[OrderDate], ROW_NUMBER() OVER(PARTITION BY [o].[CustomerID] ORDER BY [o].[OrderID]) AS [row]
+        FROM [Orders] AS [o]
+    ) AS [o0]
+    WHERE [o0].[row] <= 1
+) AS [o1] ON [c].[CustomerID] = [o1].[CustomerID]
+""");
+    }
+
     public override async Task Project_single_element_from_collection_with_OrderBy_Skip_and_FirstOrDefault(bool async)
     {
         await base.Project_single_element_from_collection_with_OrderBy_Skip_and_FirstOrDefault(async);