diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/DefaultContainer.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/DefaultContainer.cs
index 503d453f2a..c29d6c31e7 100644
--- a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/DefaultContainer.cs
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/DefaultContainer.cs
@@ -4225,6 +4225,7 @@ public CustomerInfoSingle(global::Microsoft.OData.Client.DataServiceQuerySingle<
     /// CustomerInfoId
     /// </KeyProperties>
     [global::Microsoft.OData.Client.Key("CustomerInfoId")]
+    [global::Microsoft.OData.Client.HasStream()]
     [global::Microsoft.OData.Client.OriginalNameAttribute("CustomerInfo")]
     public partial class CustomerInfo : global::Microsoft.OData.Client.BaseEntityType, global::System.ComponentModel.INotifyPropertyChanged
     {
@@ -5690,6 +5691,7 @@ public CarSingle(global::Microsoft.OData.Client.DataServiceQuerySingle<Car> quer
     /// VIN
     /// </KeyProperties>
     [global::Microsoft.OData.Client.Key("VIN")]
+    [global::Microsoft.OData.Client.HasStream()]
     [global::Microsoft.OData.Client.OriginalNameAttribute("Car")]
     public partial class Car : global::Microsoft.OData.Client.BaseEntityType, global::System.ComponentModel.INotifyPropertyChanged
     {
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/EndToEndServiceCsdl.xml b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/EndToEndServiceCsdl.xml
index 2e96664e92..8bee34dba4 100644
--- a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/EndToEndServiceCsdl.xml
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Client/EndToEnd/EndToEndServiceCsdl.xml
@@ -215,7 +215,7 @@
         <Property Name="PhotoId" Type="Edm.Int32" Nullable="false" />
         <Property Name="Photo" Type="Edm.Binary" />
       </EntityType>
-      <EntityType Name="CustomerInfo">
+      <EntityType Name="CustomerInfo" HasStream="true">
         <Key>
           <PropertyRef Name="CustomerInfoId" />
         </Key>
@@ -287,7 +287,7 @@
         <Property Name="ComplexPhone" Type="Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Phone" />
         <Property Name="ComplexContactDetails" Type="Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.ContactDetails" />
       </EntityType>
-      <EntityType Name="Car">
+      <EntityType Name="Car" HasStream="true">
         <Key>
           <PropertyRef Name="VIN" />
         </Key>
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Server/EndToEnd/CommonEndToEndDataModel.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Server/EndToEnd/CommonEndToEndDataModel.cs
index 3b6a6c66e1..ee94cd6c8c 100644
--- a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Server/EndToEnd/CommonEndToEndDataModel.cs
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/Common/Server/EndToEnd/CommonEndToEndDataModel.cs
@@ -5,6 +5,7 @@
 // </copyright>
 //------------------------------------------------------------------------------
 
+using Microsoft.OData.ModelBuilder;
 using Microsoft.Spatial;
 using EfKey = System.ComponentModel.DataAnnotations.KeyAttribute;
 
@@ -182,6 +183,7 @@ public class ProductPhoto
         public byte[]? Photo { get; set; }
     }
 
+    [MediaType]
     public class CustomerInfo
     {
         public int CustomerInfoId { get; set; }
@@ -250,6 +252,7 @@ public class MappedEntityType
         public ContactDetails? ComplexContactDetails { get; set; }
     }
 
+    [MediaType]
     public class Car
     {
         [EfKey]
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/DollarSegmentTestsController.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/DollarSegmentTestsController.cs
new file mode 100644
index 0000000000..db32cb4880
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/DollarSegmentTestsController.cs
@@ -0,0 +1,141 @@
+//---------------------------------------------------------------------
+// <copyright file="DollarSegmentTestsController.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.Mvc;
+using Microsoft.AspNetCore.OData.Formatter;
+using Microsoft.AspNetCore.OData.Query;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+
+public class DollarSegmentTestsController : ODataController
+{
+    private static CommonEndToEndDataSource _dataSource;
+
+    [EnableQuery]
+    [HttpGet("odata/People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee")]
+    public IActionResult GetPeopleOfTypeEmployee()
+    {
+        var people = _dataSource.People?.OfType<Employee>();
+        return Ok(people);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People/{key}/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Salary")]
+    public IActionResult GetEmployeeSalary([FromRoute] int key)
+    {
+        var employee = _dataSource.People?.OfType<Employee>().SingleOrDefault(a => a.PersonId == key);
+        if (employee == null)
+        {
+            return NotFound();
+        }
+        return Ok(employee.Salary);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/{key}/RelatedProducts/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/{relatedKey}/Photos")]
+    public IActionResult GetProductRelatedPhotos([FromRoute] int key, [FromRoute] int relatedKey)
+    {
+        var product = _dataSource.Products?.SingleOrDefault(a => a.ProductId == key);
+        if (product == null)
+        {
+            return NotFound();
+        }
+
+        var relatedProduct = product.RelatedProducts?.SingleOrDefault(a => a.ProductId == relatedKey);
+        if (relatedProduct == null)
+        {
+            return NotFound();
+        }
+
+        return Ok(relatedProduct.Photos);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct")]
+    public IActionResult GetDiscontinuedProducts()
+    {
+        var discontinuedProducts = _dataSource.Products?.OfType<DiscontinuedProduct>();
+
+        return Ok(discontinuedProducts);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/$")]
+    public IActionResult GetAnotherDiscontinuedProducts()
+    {
+        var discontinuedProducts = _dataSource.Products?.OfType<DiscontinuedProduct>();
+
+        return Ok(discontinuedProducts);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Products/$/$/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct")]
+    public IActionResult GetDiscontinuedProductsMultipleDollarSegments()
+    {
+        var discontinuedProducts = _dataSource.Products?.OfType<DiscontinuedProduct>();
+
+        return Ok(discontinuedProducts);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Login")]
+    public IActionResult GetLogin()
+    {
+        var login = _dataSource.Logins;
+        return Ok(login);
+    }
+
+    [HttpPost("odata/People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Default.IncreaseSalaries")]
+    public IActionResult IncreaseSalaries([FromODataBody] int n)
+    {
+        _dataSource.People?.OfType<Employee>().ToList().ForEach(e => e.Salary += n);
+        return Ok();
+    }
+
+    [HttpPost("odata/People/$/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/$/Default.IncreaseSalaries")]
+    public IActionResult IncreaseSalariesMultipleDollarSegments([FromODataBody] int n)
+    {
+        _dataSource.People?.OfType<Employee>().ToList().ForEach(e => e.Salary += n);
+        return Ok();
+    }
+
+    [HttpPost("odata/People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Default.IncreaseSalaries/$")]
+    public IActionResult IncreaseSalariesDollarSegmentAtUriEnd([FromODataBody] int n)
+    {
+        _dataSource.People?.OfType<Employee>().ToList().ForEach(e => e.Salary += n);
+        return Ok();
+    }
+
+    [HttpPost("odata/People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/{key}/$/Default.Sack")]
+    public IActionResult Sack([FromODataUri] int key)
+    {
+        var employee = _dataSource.People?.OfType<Employee>().SingleOrDefault(a => a.PersonId == key);
+        if (employee == null)
+        {
+            return NotFound();
+        }
+
+        _dataSource.People?.Remove(employee);
+        return NoContent();
+    }
+
+    [HttpPost("odata/Login")]
+    public IActionResult PostLogin([FromBody] Login login)
+    {
+        _dataSource.Logins?.Add(login);
+        return Created(login);
+    }
+
+    [HttpPost("odata/dollarsegmenttests/Default.ResetDefaultDataSource")]
+    public IActionResult ResetDefaultDataSource()
+    {
+        _dataSource = CommonEndToEndDataSource.CreateInstance();
+
+        return Ok();
+    }
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/KeyAsSegmentTestsController.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/KeyAsSegmentTestsController.cs
new file mode 100644
index 0000000000..c984ad7512
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/KeyAsSegmentTestsController.cs
@@ -0,0 +1,203 @@
+//---------------------------------------------------------------------
+// <copyright file="KeyAsSegmentTestsController.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.Mvc;
+using Microsoft.AspNetCore.OData.Formatter;
+using Microsoft.AspNetCore.OData.Query;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+
+public class KeyAsSegmentTestsController : ODataController
+{
+    private static CommonEndToEndDataSource _dataSource;
+
+    [EnableQuery]
+    [HttpGet("odata/People")]
+    public IActionResult GetPeople()
+    {
+        var people = _dataSource.People;
+        return Ok(people);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee")]
+    public IActionResult GetPeopleOfTypeEmployee()
+    {
+        var people = _dataSource.People?.OfType<Employee>();
+        return Ok(people);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People({key})")]
+    public IActionResult GetPerson([FromRoute] int key)
+    {
+        var person = _dataSource.People?.SingleOrDefault(a => a.PersonId == key);
+        if (person == null)
+        {
+            return NotFound();
+        }
+        return Ok(person);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People/{key}")]
+    public IActionResult GetPersonById([FromRoute] int key)
+    {
+        var person = _dataSource.People?.SingleOrDefault(a => a.PersonId == key);
+        if (person == null)
+        {
+            return NotFound();
+        }
+        return Ok(person);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People/{key}/PersonMetadata")]
+    public IActionResult GetPersonMetadatada([FromRoute] int key)
+    {
+        var person = _dataSource.People?.SingleOrDefault(a => a.PersonId == key);
+        if (person == null)
+        {
+            return NotFound();
+        }
+        return Ok(person.PersonMetadata);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/{key}/RelatedProducts/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/{relatedKey}/Photos")]
+    public IActionResult GetProductRelatedPhotos([FromRoute] int key, [FromRoute] int relatedKey)
+    {
+        var product = _dataSource.Products?.SingleOrDefault(a => a.ProductId == key);
+        if (product == null)
+        {
+            return NotFound();
+        }
+
+        var relatedProduct = product.RelatedProducts?.SingleOrDefault(a => a.ProductId == relatedKey);
+        if (relatedProduct == null)
+        {
+            return NotFound();
+        }
+
+        return Ok(relatedProduct.Photos);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Orders({key})")]
+    public IActionResult GetProduct([FromRoute] int key)
+    {
+        var order = _dataSource.Orders?.SingleOrDefault(a => a.OrderId == key);
+        if (order == null)
+        {
+            return NotFound();
+        }
+        return Ok(order);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Customers")]
+    public IActionResult GetCustomers()
+    {
+        var customers = _dataSource.Customers;
+        return Ok(customers);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Customers/{key}")]
+    public IActionResult GetCustomer([FromODataUri] int key)
+    {
+        var customer = _dataSource.Customers?.SingleOrDefault(c => c.CustomerId == key);
+        if (customer == null)
+        {
+            return NotFound();
+        }
+
+        return Ok(customer);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/CustomerInfos")]
+    public IActionResult GetCustomerInfos()
+    {
+        var customerInfos = _dataSource.CustomerInfos;
+        return Ok(customerInfos);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/CustomerInfos({key})/$value")]
+    public IActionResult GetCustomerInfosValue([FromODataUri] int key)
+    {
+        var customerInfo = _dataSource.CustomerInfos?.SingleOrDefault(c => c.CustomerInfoId == key);
+        if (customerInfo == null)
+        {
+            return NotFound();
+        }
+
+        return Ok(customerInfo);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Cars")]
+    public IActionResult GetCars()
+    {
+        var cars = _dataSource.Cars;
+        return Ok(cars);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Cars({key})/Photo")]
+    public IActionResult GetCarPhoto([FromODataUri] int key)
+    {
+        var car = _dataSource.Cars?.SingleOrDefault(c => c.VIN == key);
+        if (car == null)
+        {
+            return NotFound();
+        }
+
+        car.Photo = new MemoryStream([0x00, 0x01, 0x02, 0x03, 0x04, 0x05, 0x06, 0x07, 0x08, 0x09, 0x0a, 0x0b, 0x0c, 0x0d, 0x0e, 0x0f]);
+
+        return Ok(car.Photo);
+    }
+
+    [HttpPut("odata/Cars({key})/Video")]
+    public IActionResult AddVideoToCar([FromODataUri] int key)
+    {
+        var car = _dataSource.Cars?.SingleOrDefault(c => c.VIN == key);
+        if (car == null)
+        {
+            return NotFound();
+        }
+
+        var video = Request.Body;
+        car.Video = video;
+        return Updated(car);
+    }
+
+    [EnableQuery]
+    [HttpPut("odata/CustomerInfos({key})/$value")]
+    public IActionResult AddStreamValueToCustomerInfo([FromODataUri] int key)
+    {
+        var customerInfo = _dataSource.CustomerInfos?.SingleOrDefault(c => c.CustomerInfoId == key);
+        if (customerInfo == null)
+        {
+            return NotFound();
+        }
+
+        var stream = Request.Body;
+
+        return Updated(customerInfo);
+    }
+
+    [HttpPost("odata/keyassegmenttests/Default.ResetDefaultDataSource")]
+    public IActionResult ResetDefaultDataSource()
+    {
+        _dataSource = CommonEndToEndDataSource.CreateInstance();
+
+        return Ok();
+    }
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/LiteralFormatTestsController.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/LiteralFormatTestsController.cs
new file mode 100644
index 0000000000..72b21b362c
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/LiteralFormatTestsController.cs
@@ -0,0 +1,108 @@
+//---------------------------------------------------------------------
+// <copyright file="LiteralFormatTestsController.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.Mvc;
+using Microsoft.AspNetCore.OData.Formatter;
+using Microsoft.AspNetCore.OData.Query;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+
+public class LiteralFormatTestsController : ODataController
+{
+    private static CommonEndToEndDataSource _dataSource;
+
+    [EnableQuery]
+    [HttpGet("odata/Customers")]
+    public IActionResult GetCustomers()
+    {
+        var customers = _dataSource.Customers;
+        return Ok(customers);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Customers/{key}")]
+    public IActionResult GetCustomer([FromODataUri] int key)
+    {
+        var customer = _dataSource.Customers?.SingleOrDefault(c => c.CustomerId == key);
+        if (customer == null)
+        {
+            return NotFound();
+        }
+
+        return Ok(customer);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Login")]
+    public IActionResult GetLogin()
+    {
+        var login = _dataSource.Logins;
+        return Ok(login);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Login/{key}/Customer")]
+    public IActionResult GetLoginCustomers([FromODataUri] string key)
+    {
+        var login = _dataSource.Logins?.SingleOrDefault(l => l.Username == key);
+        if (login == null)
+        {
+            return NotFound();
+        }
+
+        return Ok(login.Customer);
+    }
+
+    [HttpPost("odata/Login")]
+    public IActionResult AddLogin([FromBody] Login login)
+    {
+        _dataSource.Logins?.Add(login);
+        return Created(login);
+    }
+
+    [HttpPost("odata/Customers({key})/Logins/$ref")]
+    public IActionResult AddLoginsRefToCustomer([FromODataUri] int key, [FromBody] Uri loginUri)
+    {
+        if (loginUri == null)
+        {
+            return BadRequest();
+        }
+
+        // Extract the login ID from the URI
+        var lastSegment = loginUri.Segments.Last();
+        int startIndex = lastSegment.IndexOf("('") + 2; // +2 to skip the opening parenthesis and the single quote
+        int endIndex = lastSegment.IndexOf("')") - 1; // -1 to skip the closing single quote
+
+        var loginUserName = Uri.UnescapeDataString(lastSegment.Substring(startIndex, endIndex - startIndex + 1));
+
+        // Find the login by ID
+        var login = _dataSource.Logins?.SingleOrDefault(d => d.Username == loginUserName);
+        if (login == null)
+        {
+            return NotFound();
+        }
+
+        var customer = _dataSource.Customers?.SingleOrDefault(c => c.CustomerId == key);
+        if (customer == null)
+        {
+            return NotFound();
+        }
+
+        customer.Logins?.Add(login); 
+
+        return Ok(login);
+    }
+
+    [HttpPost("odata/keyasssegmentliteralformattests/Default.ResetDefaultDataSource")]
+    public IActionResult ResetDefaultDataSource()
+    {
+        _dataSource = CommonEndToEndDataSource.CreateInstance();
+
+        return Ok();
+    }
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/UpdateTestsController.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/UpdateTestsController.cs
new file mode 100644
index 0000000000..5fa551ba0d
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Server/UpdateTestsController.cs
@@ -0,0 +1,249 @@
+//---------------------------------------------------------------------
+// <copyright file="UpdateTestsController.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.Mvc;
+using Microsoft.AspNetCore.OData.Deltas;
+using Microsoft.AspNetCore.OData.Formatter;
+using Microsoft.AspNetCore.OData.Query;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+
+public class UpdateTestsController : ODataController
+{
+    private static CommonEndToEndDataSource _dataSource;
+
+    [EnableQuery]
+    [HttpGet("odata/People")]
+    public IActionResult GetPeople()
+    {
+        var people = _dataSource.People;
+        return Ok(people);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee")]
+    public IActionResult GetPeopleOfTypeEmployee()
+    {
+        var people = _dataSource.People?.OfType<Employee>();
+        return Ok(people);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People({key})")]
+    public IActionResult GetPerson([FromRoute] int key)
+    {
+        var person = _dataSource.People?.SingleOrDefault(a => a.PersonId == key);
+        if (person == null)
+        {
+            return NotFound();
+        }
+        return Ok(person);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/People/{key}")]
+    public IActionResult GetPersonById([FromRoute] int key)
+    {
+        var person = _dataSource.People?.SingleOrDefault(a => a.PersonId == key);
+        if (person == null)
+        {
+            return NotFound();
+        }
+        return Ok(person);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Orders")]
+    public IActionResult GetOrders()
+    {
+        var orders = _dataSource.Orders;
+        return Ok(orders);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Customers")]
+    public IActionResult GetCustomers()
+    {
+        var customers = _dataSource.Customers;
+        return Ok(customers);
+    }
+
+    [EnableQuery]
+    [HttpGet("odata/Customers/{key}")]
+    public IActionResult GetCustomer([FromODataUri] int key)
+    {
+        var customer = _dataSource.Customers?.SingleOrDefault(c => c.CustomerId == key);
+        if (customer == null)
+        {
+            return NotFound();
+        }
+
+        return Ok(customer);
+    }
+
+    [HttpPost("odata/People")]
+    public IActionResult AddPerson([FromBody] Person person)
+    {
+        _dataSource.People?.Add(person);
+        return Created(person);
+    }
+
+    [HttpPost("odata/Customers")]
+    public IActionResult AddCustomer([FromBody] Customer customer)
+    {
+        _dataSource.Customers?.Add(customer);
+        return Created(customer);
+    }
+
+    [HttpPost("odata/Customers({key})/Orders")]
+    public IActionResult AddOrderToCustomer([FromODataUri] int key, [FromBody] Order order)
+    {
+        var customer = _dataSource.Customers?.SingleOrDefault(c => c.CustomerId == key);
+        if (customer == null)
+        {
+            return NotFound();
+        }
+
+        customer.Orders?.Add(order);
+        return Created(order);
+    }
+
+    [HttpPost("odata/Customers({key})/Orders/$ref")]
+    public IActionResult AddOrderRefToCustomer([FromODataUri] int key, [FromBody] Uri orderUri)
+    {
+        if (orderUri == null)
+        {
+            return BadRequest();
+        }
+
+        // Extract the ID from the URI
+        var lastSegment = orderUri.Segments.Last();
+        int startIndex = lastSegment.IndexOf('(') + 1; 
+        int endIndex = lastSegment.IndexOf(')') - 1;
+        var orderId = int.Parse(Uri.UnescapeDataString(lastSegment.Substring(startIndex, endIndex - startIndex + 1)));
+
+        // Find the order by ID
+        var order = _dataSource.Orders?.SingleOrDefault(d => d.OrderId == orderId);
+        if (order == null)
+        {
+            return NotFound();
+        }
+
+        // Add the order reference to the customer
+        var customer = _dataSource.Customers?.SingleOrDefault(c => c.CustomerId == key);
+        if (customer == null)
+        {
+            return NotFound();
+        }
+
+        customer.Orders?.Add(order);
+
+        return Ok(customer);
+    }
+
+    [HttpPut("odata/People({key})/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.SpecialEmployee/Manager/$ref")]
+    public IActionResult UpdateEmployeeManager([FromODataUri] int key, [FromBody] Uri managerUri)
+    {
+        if (managerUri == null)
+        {
+            return BadRequest();
+        }
+
+        // Extract the ID from the URI
+        var lastSegment = managerUri.Segments.Last();
+        int startIndex = lastSegment.IndexOf('(') + 1;
+        int endIndex = lastSegment.IndexOf(')') - 1;
+        var managerId = int.Parse(Uri.UnescapeDataString(lastSegment.Substring(startIndex, endIndex - startIndex + 1)));
+
+        // Find the order by ID
+        var manager = _dataSource.People?.OfType<Employee>().SingleOrDefault(d => d.PersonId == managerId);
+        if (manager == null)
+        {
+            return NotFound();
+        }
+
+        var employee = _dataSource.People?.OfType<SpecialEmployee>().SingleOrDefault(c => c.PersonId == key);
+        if (employee == null)
+        {
+            return NotFound();
+        }
+
+        // Update the employee manager
+        employee.Manager = manager;
+
+        return Ok(employee);
+    }
+
+    [HttpPatch("odata/People/{key}")]
+    public IActionResult PatchPerson([FromRoute] int key, [FromBody] Delta<Person> patch)
+    {
+        var person = _dataSource.People?.SingleOrDefault(a => a.PersonId == key);
+        if (person == null)
+        {
+            return NotFound();
+        }
+        patch.Patch(person);
+        return Updated(person);
+    }
+
+    [HttpDelete("odata/People({key})/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.SpecialEmployee")]
+    public IActionResult DeleteSpecialEmployee([FromRoute] int key)
+    {
+        var person = _dataSource.People?.SingleOrDefault(a => a.PersonId == key);
+        if (person == null)
+        {
+            return NotFound();
+        }
+
+        _dataSource.People?.Remove(person);
+        return NoContent();
+    }
+
+    [HttpDelete("odata/Customers({key})/Orders/$ref")]
+    public IActionResult RemoveOrderRefFromCustomer([FromODataUri] int key)
+    {
+        string? id = Request.Query["$id"];
+        var orderUri = id != null ? new Uri(id) : null;
+
+        if (orderUri == null)
+        {
+            return BadRequest();
+        }
+
+        // Extract the ID from the URI
+        var lastSegment = orderUri.Segments.Last();
+        int startIndex = lastSegment.IndexOf('(') + 1;
+        int endIndex = lastSegment.IndexOf(')') - 1;
+        var orderId = int.Parse(Uri.UnescapeDataString(lastSegment.Substring(startIndex, endIndex - startIndex + 1)));
+
+        // Find the order by ID
+        var order = _dataSource.Orders?.SingleOrDefault(d => d.OrderId == orderId);
+        if (order == null)
+        {
+            return NotFound();
+        }
+
+        // Remove the order reference from the customer
+        var customer = _dataSource.Customers?.SingleOrDefault(c => c.CustomerId == key);
+        if (customer == null)
+        {
+            return NotFound();
+        }
+
+        customer.Orders?.Remove(order);
+        return Ok(customer);
+    }
+
+    [HttpPost("odata/keyassegmentupdatetests/Default.ResetDefaultDataSource")]
+    public IActionResult ResetDefaultDataSource()
+    {
+        _dataSource = CommonEndToEndDataSource.CreateInstance();
+
+        return Ok();
+    }
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/ClientKeyAsSegmentTests.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/ClientKeyAsSegmentTests.cs
new file mode 100644
index 0000000000..739e7f1dae
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/ClientKeyAsSegmentTests.cs
@@ -0,0 +1,320 @@
+//---------------------------------------------------------------------
+// <copyright file="ClientUrlConventionsTests.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.OData;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.OData.Client.E2E.TestCommon;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Default;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+using Xunit;
+using Customer = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Customer;
+using Employee = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Employee;
+using Person = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Person;
+using SpecialEmployee = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.SpecialEmployee;
+using DiscontinuedProduct = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.DiscontinuedProduct;
+using ProductPhoto = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.ProductPhoto;
+using Order = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Order;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Tests;
+
+public class ClientKeyAsSegmentTests : EndToEndTestBase<ClientKeyAsSegmentTests.TestsStartup>
+{
+    private readonly Uri _baseUri;
+    private readonly Container _context;
+
+    public class TestsStartup : TestStartupBase
+    {
+        public override void ConfigureServices(IServiceCollection services)
+        {
+            services.ConfigureControllers(typeof(KeyAsSegmentTestsController), typeof(MetadataController));
+
+            services.AddControllers().AddOData(opt =>
+                opt.EnableQueryFeatures().AddRouteComponents("odata", CommonEndToEndEdmModel.GetEdmModel()));
+        }
+    }
+
+    public ClientKeyAsSegmentTests(TestWebApplicationFactory<TestsStartup> fixture) : base(fixture)
+    {
+        if (Client.BaseAddress == null)
+        {
+            throw new ArgumentNullException(nameof(Client.BaseAddress), "Base address cannot be null");
+        }
+
+        _baseUri = new Uri(Client.BaseAddress, "odata/");
+
+        _context = new Container(_baseUri)
+        {
+            HttpClientFactory = HttpClientFactory
+        };
+
+        ResetDefaultDataSource();
+    }
+
+    [Fact]
+    public void ClientChangesUrlConventionsBetweenQueries()
+    {
+        // Arrange & Act & Assert
+        var contextWrapper = this.CreateWrappedContext();
+
+        var query = contextWrapper.CreateQuery<Customer>("Customers").OrderBy(c => c.CustomerId).ToList();
+        Assert.Equal(10, query.Count);
+
+        contextWrapper.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Parentheses;
+        var queryWithDefaultKeys = contextWrapper.CreateQuery<Customer>("Customers").OrderBy(c => c.CustomerId).ToList();
+        Assert.Equal(10, queryWithDefaultKeys.Count);
+        Assert.Equal(query, queryWithDefaultKeys);
+
+        contextWrapper.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        query = contextWrapper.CreateQuery<Customer>("Customers").OrderBy(c => c.CustomerId).ToList();
+        Assert.Equal(10, query.Count);
+        Assert.Equal(query, queryWithDefaultKeys);
+    }
+
+    [Fact]
+    public void GetSingleEntityWithKeyAsSegment()
+    {
+        // Arrange & Act
+        var contextWrapper = this.CreateWrappedContext();
+
+        var queryByKey = contextWrapper.CreateQuery<Person>("People").ByKey(-10);
+        var personByKey = queryByKey.GetValue();
+
+        var query = contextWrapper.CreateQuery<Person>("People").Where(p => p.PersonId == -10) as DataServiceQuery<Person>;
+
+        // Assert
+        Assert.EndsWith("/odata/People/-10", queryByKey.RequestUri.OriginalString);
+        Assert.EndsWith("/odata/People?$filter=PersonId eq -10", query?.RequestUri.OriginalString);
+        Assert.NotNull(personByKey);
+        Assert.Equal(personByKey, query?.SingleOrDefault());
+
+        Assert.Equal("ぺソぞ弌タァ匚タぽひハ欲ぴほ匚せまたバボチマ匚ぁゾソチぁЯそぁミя暦畚ボ歹ひЯほダチそЯせぽゼポЯチａた歹たをタマせをせ匚ミタひぜ畚暦グクひほそたグせяチ匚ｦぺぁ", personByKey.Name);
+        Assert.Equal(4091, (personByKey as Employee)?.Salary);
+        Assert.Equal(-37730565, (personByKey as SpecialEmployee)?.Bonus);
+    }
+
+    [Fact]
+    public void LinqQueryWithKeyUsingMethodSyntax()
+    {
+        // Arrange & Act
+        var contextWrapper = this.CreateWrappedContext();
+
+        var queryByKey = contextWrapper.People.ByKey(-10);
+        var personByKey = queryByKey.GetValue();
+
+        var query = contextWrapper.People.Where(p => p.PersonId == -10);
+
+        // Assert
+        Assert.EndsWith("/odata/People/-10", queryByKey.RequestUri.OriginalString);
+        Assert.EndsWith("/odata/People?$filter=PersonId eq -10", query?.ToString());
+        Assert.NotNull(personByKey);
+        Assert.Equal(personByKey, query?.SingleOrDefault());
+
+        Assert.Equal("ぺソぞ弌タァ匚タぽひハ欲ぴほ匚せまたバボチマ匚ぁゾソチぁЯそぁミя暦畚ボ歹ひЯほダチそЯせぽゼポЯチａた歹たをタマせをせ匚ミタひぜ畚暦グクひほそたグせяチ匚ｦぺぁ", personByKey.Name);
+        Assert.Equal(4091, (personByKey as Employee)?.Salary);
+        Assert.Equal(-37730565, (personByKey as SpecialEmployee)?.Bonus);
+    }
+
+    [Fact]
+    public void LinqQueryWithNullStringInKey()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        var query =
+            from p in contextWrapper.People
+            where p.Name == "\0te\0st\0"
+            select p;
+
+        // Act
+        var person = query.SingleOrDefault();
+
+        // Assert
+        Assert.Contains("/odata/People?$filter=Name eq '%00te%00st%00'", query.ToString());
+        Assert.Null(person);
+    }
+
+    [Fact]
+    public void LinqQueryWithKey()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        var query =
+            from p in contextWrapper.People
+            where p.PersonId == -10
+            select p;
+
+        // Act
+        var person = query.SingleOrDefault();
+
+        // Assert
+        Assert.Contains("/odata/People?$filter=PersonId eq -10", query.ToString());
+        Assert.NotNull(person);
+
+        Assert.Equal("ぺソぞ弌タァ匚タぽひハ欲ぴほ匚せまたバボチマ匚ぁゾソチぁЯそぁミя暦畚ボ歹ひЯほダチそЯせぽゼポЯチａた歹たをタマせをせ匚ミタひぜ畚暦グクひほそたグせяチ匚ｦぺぁ", person.Name);
+        Assert.Equal(4091, (person as Employee)?.Salary);
+        Assert.Equal(-37730565, (person as SpecialEmployee)?.Bonus);
+    }
+
+    [Fact]
+    public void LinqQueryWithKeyAndOfType()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        var query = (
+            from p in contextWrapper.People.OfType<Employee>()
+            where p.PersonId == -6
+            select p) as DataServiceQuery<Employee>;
+
+        // Act
+        var employee = query?.FirstOrDefault();
+
+        // Assert
+        Assert.IsType<Employee>(employee);
+        Assert.EndsWith("odata/People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee?$filter=PersonId eq -6", query?.ToString());
+        Assert.NotNull(employee);
+        Assert.Equal("vnqfkvpolnxvurgxpfbfquqrqxqxknjykkuapsqcmbeuslhkqufultvr", employee.Name);
+        Assert.Equal(2147483647, employee.Salary);
+    }
+
+    [Fact]
+    public void MultipleNavigationAndOfTypeInQuery()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        var query = (
+            from product in contextWrapper.Products.OfType<DiscontinuedProduct>()
+            from related in product.RelatedProducts.OfType<DiscontinuedProduct>()
+            from photo in related.Photos
+            where
+                product.ProductId == -9 &&
+                related.ProductId == -9 &&
+                photo.PhotoId == -4 &&
+                photo.ProductId == -4
+
+            select photo) as IQueryable<ProductPhoto>;
+
+        // Act
+        var photoResult = query?.SingleOrDefault();
+
+        // Assert
+        Assert.EndsWith(
+            "odata/Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/-9/RelatedProducts/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/-9/Photos?$filter=PhotoId eq -4 and ProductId eq -4",
+            query?.ToString());
+
+        Assert.NotNull(photoResult);
+        Assert.Equal(-4, photoResult.PhotoId);
+        Assert.Equal(-4, photoResult.ProductId);
+    }
+
+    [Fact]
+    public void AttachToWithKeyAsSegment()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        var person = new Person { PersonId = -10 };
+
+        // Act
+        contextWrapper.AttachTo("Person", person);
+
+        // Assert
+        Assert.Single(contextWrapper.Entities);
+        Assert.Equal(-10, (contextWrapper.Entities[0].Entity as Person)?.PersonId);
+    }
+
+    [Fact]
+    public void AttachToAndLoadPropertyWithKeyAsSegment()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        var person = new Person { PersonId = -10 };
+
+        // Act
+        contextWrapper.AttachTo("People", person);
+        contextWrapper.LoadProperty(person, "PersonMetadata");
+
+        // Assert
+        Assert.Equal(3, person.PersonMetadata.Count);
+        Assert.Equal("ysjrkvxlmdiddnrpxvnizyqvsfurnvhiugqyukiyedbrzgpqlevdfeqainzoauyqvzkx", person.PersonMetadata.Where(p => p.PersonMetadataId == -7).Single().PropertyValue);
+        Assert.Equal("ァ亜ぽﾈソぽひァミａ弌ゾダソポぼタ黑歹九ぁんЯﾝёゼミァ弌タ九ｦぞチポポЯぺｚたダゾゾﾝミポチａタマぴ欲яﾈタЯ亜まａあ", person.PersonMetadata.Where(p => p.PersonMetadataId == -9).Single().PropertyValue);
+        Assert.Equal("lazcbjlydpauujlvßgszchoxhycaryzbmkuskiqfxyiu", person.PersonMetadata.Where(p => p.PersonMetadataId == -10).Single().PropertyValue);
+    }
+
+    [Fact]
+    public void LoadPropertyWithNextLink()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        var response = contextWrapper.Customers.Expand(c => c.Orders).Execute() as QueryOperationResponse<Customer>;
+        DataServiceQueryContinuation<Customer>? customerContinuation = null;
+
+        do
+        {
+            if (customerContinuation != null)
+            {
+                response = contextWrapper.Execute<Customer>(customerContinuation);
+            }
+
+            foreach (var customer in response)
+            {
+                DataServiceQueryContinuation<Order> orderContinuation = response.GetContinuation(customer.Orders);
+
+                while (orderContinuation != null)
+                {
+                    var ordersResponse = contextWrapper.LoadProperty(customer, "Orders", orderContinuation);
+                    orderContinuation = ordersResponse.GetContinuation();
+                }
+            }
+
+        } while ((customerContinuation = response.GetContinuation()) != null);
+    }
+
+
+    [Fact]
+    public void ClientWithKeyAsSegmentSendsRequestsToServerWithoutKeyAsSegment()
+    {
+        // Arrange
+        var contextWrapper = this.CreateWrappedContext();
+
+        // Act
+        var queryable = contextWrapper.Orders.ByKey(0);
+        var exception = Record.Exception(() => queryable.GetValue());
+
+        // Assert
+        Assert.EndsWith("/Orders/0", queryable.RequestUri.OriginalString);
+        Assert.NotNull(exception.InnerException);
+        Assert.IsType<DataServiceClientException>(exception.InnerException);
+    }
+
+    #region Private methods
+
+    private Container CreateWrappedContext()
+    {
+        var context = new Container(_baseUri)
+        {
+            HttpClientFactory = HttpClientFactory,
+            UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash
+        };
+
+        return context;
+    }
+
+    private void ResetDefaultDataSource()
+    {
+        var actionUri = new Uri(_baseUri + "keyassegmenttests/Default.ResetDefaultDataSource", UriKind.Absolute);
+        _context.Execute(actionUri, "POST");
+    }
+
+    #endregion
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/DollarSegmentTests.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/DollarSegmentTests.cs
new file mode 100644
index 0000000000..cebe5d2354
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/DollarSegmentTests.cs
@@ -0,0 +1,252 @@
+//---------------------------------------------------------------------
+// <copyright file="DollarSegmentTests.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.OData;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.OData.Client.E2E.TestCommon;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Default;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+using Microsoft.OData.Edm;
+using Xunit;
+using DiscontinuedProduct = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.DiscontinuedProduct;
+using Employee = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Employee;
+using Login = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Login;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Tests;
+
+public class DollarSegmentTests : EndToEndTestBase<DollarSegmentTests.TestsStartup>
+{
+    private readonly Uri _baseUri;
+    private readonly Container _context;
+    private readonly IEdmModel _model;
+
+    public class TestsStartup : TestStartupBase
+    {
+        public override void ConfigureServices(IServiceCollection services)
+        {
+            services.ConfigureControllers(typeof(DollarSegmentTestsController), typeof(MetadataController));
+
+            services.AddControllers().AddOData(opt =>
+                opt.EnableQueryFeatures().AddRouteComponents("odata", CommonEndToEndEdmModel.GetEdmModel()));
+        }
+    }
+
+    public DollarSegmentTests(TestWebApplicationFactory<TestsStartup> fixture) : base(fixture)
+    {
+        if (Client.BaseAddress == null)
+        {
+            throw new ArgumentNullException(nameof(Client.BaseAddress), "Base address cannot be null");
+        }
+
+        _baseUri = new Uri(Client.BaseAddress, "odata/");
+
+        _context = new Container(_baseUri)
+        {
+            HttpClientFactory = HttpClientFactory
+        };
+
+        _model = CommonEndToEndEdmModel.GetEdmModel();
+        ResetDefaultDataSource();
+    }
+
+    [Fact]
+    public void InsertEntityWithKeyValueSameAsNavigationPropertyName()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+
+        var newLogin = new Login { Username = "LastLogin", CustomerId = -289 };
+
+        // Act
+        _context.AddToLogin(newLogin);
+        _context.SaveChanges();
+
+        var loginQuery = _context.CreateQuery<Login>("Login").Where(l => l.Username == "LastLogin").ToArray();
+
+        // Assert
+        var queried = Assert.Single(loginQuery);
+        Assert.True(newLogin == queried, "Query result does not equal newly added login");
+        Assert.Equal(-289, queried.CustomerId);
+    }
+
+    [Fact]
+    public void ClientExecuteEntitySetDerivedType()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var requestUri = new Uri(_baseUri + "Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct");
+
+        // Act
+        var discontinuedProductQuery = _context.Execute<DiscontinuedProduct>(requestUri).ToArray();
+
+        // Assert
+        Assert.Equal(5, discontinuedProductQuery.Length);
+        var discontinuedProduct = discontinuedProductQuery.Where(d => d.ProductId == -3).Single();
+        Assert.Equal("ißuhmxavnmlsssssjssagmqjpchjußtkcoaldeyyduarovnxspzsskufxxfltußtxfhgjlksrn", discontinuedProduct.Description);
+        Assert.Equal(-1002345821, discontinuedProduct.ReplacementProductId);
+        Assert.Equal("そ歹ソボボをグ裹ぴポｦチ", discontinuedProduct.ChildConcurrencyToken);
+    }
+
+    [Fact]
+    public void ClientExecuteEntitySetDerivedTypeDollarSegmentAtEnd()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var requestUri = new Uri(_baseUri + "Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct/$");
+
+        // Act
+        var discontinuedProductQuery = _context.Execute<DiscontinuedProduct>(requestUri).ToArray();
+
+        // Assert
+        Assert.Equal(5, discontinuedProductQuery.Length);
+        var discontinuedProduct = discontinuedProductQuery.Where(d => d.ProductId == -3).Single();
+        Assert.Equal("ißuhmxavnmlsssssjssagmqjpchjußtkcoaldeyyduarovnxspzsskufxxfltußtxfhgjlksrn", discontinuedProduct.Description);
+        Assert.Equal(-1002345821, discontinuedProduct.ReplacementProductId);
+        Assert.Equal("そ歹ソボボをグ裹ぴポｦチ", discontinuedProduct.ChildConcurrencyToken);
+    }
+
+    [Fact]
+    public void ClientExecuteProjectPropertyDefinedOnDerivedType()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var requestUri = new Uri(_baseUri + "Products/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct?$select=Discontinued");
+
+        // Act
+        var discontinuedProductDatesQuery = _context.Execute<DiscontinuedProduct>(requestUri).ToArray();
+
+        // Assert
+        Assert.Equal(5, discontinuedProductDatesQuery.Length);
+        Assert.Single(discontinuedProductDatesQuery.Where(d => d.Discontinued.ToString() == "7/28/2005 1:09:56 PM +00:00"));
+    }
+
+    [Fact]
+    public void ClientExecuteProjectPropertyDefinedOnDerivedTypeMultipleDollarSegments()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var requestUri = new Uri(_baseUri + "Products/$/$/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.DiscontinuedProduct?$select=Discontinued");
+
+        // Act
+        var discontinuedProductDatesQuery = _context.Execute<DiscontinuedProduct>(requestUri).ToArray();
+
+        // Assert
+        Assert.Equal(5, discontinuedProductDatesQuery.Length);
+        Assert.Single(discontinuedProductDatesQuery.Where(d => d.Discontinued.ToString() == "7/28/2005 1:09:56 PM +00:00"));
+    }
+
+    [Fact]
+    public void InvokeFeedBoundActionDefinedOnDerivedType()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        long salaryBeforeIncrementForEmployee_6 = 2147483647;
+
+        var requestUri = new Uri(_baseUri + "People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Default.IncreaseSalaries");
+
+        // Act
+        var response = _context.Execute(
+            requestUri,
+            "POST",
+            new OperationParameter[]
+            {
+                    new BodyOperationParameter("n", 200),
+            });
+
+        // Assert
+        Assert.Equal(200, response.StatusCode);
+        var salaryAfterIncrement = _context.Execute<int>(new Uri(_baseUri + "People/-6/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Salary"));
+        Assert.Equal(salaryBeforeIncrementForEmployee_6, salaryAfterIncrement.Single() - 200);
+
+        ResetDefaultDataSource();
+    }
+
+    [Fact]
+    public void InvokeEntryBoundActionDefinedOnDerivedType()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var totalEmployeesBeforeSack = 7;
+        var requestUri = new Uri(_baseUri + "People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/-10/$/Default.Sack");
+
+        // Act
+        var response = _context.Execute(
+            requestUri,
+            "POST",
+            new OperationParameter[] { });
+
+        // Assert
+        Assert.Equal(204, response.StatusCode);
+
+        var totalEmployeesAfterSack = _context.Execute<Employee>(new Uri(_baseUri + "People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee")).Count();
+        Assert.Equal(totalEmployeesBeforeSack, totalEmployeesAfterSack + 1);
+
+        ResetDefaultDataSource();
+    }
+
+    [Fact]
+    public void InvokeActionDefinedOnDerivedTypeMultipleDollarSegments()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        long salaryBeforeIncrementForEmployee_6 = 2147483647;
+        var requestUri = new Uri(_baseUri + "People/$/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/$/Default.IncreaseSalaries");
+
+        // Act
+        var response = _context.Execute(
+            requestUri,
+            "POST",
+            new OperationParameter[]
+                {
+                        new BodyOperationParameter("n", -200),
+                });
+
+        // Assert
+        Assert.Equal(200, response.StatusCode);
+        var salaryAfterIncrement = _context.Execute<int>(new Uri(_baseUri + "People/-6/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Salary"));
+        Assert.Equal(salaryBeforeIncrementForEmployee_6, salaryAfterIncrement.Single() + 200);
+
+        ResetDefaultDataSource();
+    }
+
+    [Fact]
+    public void InvokeActionDefinedOnDerivedTypeDollarSegmentAtUriEnd()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        long salaryBeforeIncrementForEmployee_6 = 2147483647;
+        var requestUri = new Uri(_baseUri + "People/$/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Default.IncreaseSalaries/$");
+
+        // Act
+        // Actions must be leaf segments, we do not allow anything to follow them
+        var response = _context.Execute(
+            requestUri,
+            "POST",
+            new OperationParameter[]
+            {
+                    new BodyOperationParameter("n", -200),
+            });
+
+        // Assert
+        Assert.Equal(200, response.StatusCode);
+        var salaryAfterIncrement = _context.Execute<int>(new Uri(_baseUri + "People/-6/Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd.Employee/$/Salary"));
+        Assert.Equal(salaryBeforeIncrementForEmployee_6, salaryAfterIncrement.Single() + 200);
+
+        ResetDefaultDataSource();
+    }
+
+    #region Private methods
+
+    private void ResetDefaultDataSource()
+    {
+        var actionUri = new Uri(_baseUri + "dollarsegmenttests/Default.ResetDefaultDataSource", UriKind.Absolute);
+        _context.Execute(actionUri, "POST");
+    }
+
+    #endregion
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/KeyAsSegmentTestHelper.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/KeyAsSegmentTestHelper.cs
new file mode 100644
index 0000000000..ba6282f853
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/KeyAsSegmentTestHelper.cs
@@ -0,0 +1,32 @@
+//---------------------------------------------------------------------
+// <copyright file="DollarSegmentTests.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Default;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Tests;
+
+public class KeyAsSegmentTestHelper
+{
+    private readonly Uri _baseUri;
+    private readonly Container _context;
+
+    public KeyAsSegmentTestHelper(Uri serviceBaseUri, Container context)
+    {
+        this._baseUri = serviceBaseUri;
+        _context = context;
+    }
+
+    public Container CreateWrappedContext()
+    {
+        var context = new Container(this._baseUri)
+        {
+            HttpClientFactory = _context.HttpClientFactory,
+            UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash
+        };
+
+        return context;
+    }
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/LiteralFormatTests.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/LiteralFormatTests.cs
new file mode 100644
index 0000000000..6b61f16637
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/LiteralFormatTests.cs
@@ -0,0 +1,163 @@
+//---------------------------------------------------------------------
+// <copyright file="LiteralFormatTests.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.OData;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.OData.Client.E2E.TestCommon;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Default;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+using Microsoft.OData.Edm;
+using Xunit;
+using Login = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Login;
+using Customer = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Customer;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Tests;
+
+public class LiteralFormatTests : EndToEndTestBase<LiteralFormatTests.TestsStartup>
+{
+    private readonly Uri _baseUri;
+    private readonly Container _context;
+    private readonly IEdmModel _model;
+
+    public class TestsStartup : TestStartupBase
+    {
+        public override void ConfigureServices(IServiceCollection services)
+        {
+            services.ConfigureControllers(typeof(LiteralFormatTestsController), typeof(MetadataController));
+
+            services.AddControllers().AddOData(opt =>
+                opt.EnableQueryFeatures().AddRouteComponents("odata", CommonEndToEndEdmModel.GetEdmModel()));
+        }
+    }
+
+    public LiteralFormatTests(TestWebApplicationFactory<TestsStartup> fixture) : base(fixture)
+    {
+        if (Client.BaseAddress == null)
+        {
+            throw new ArgumentNullException(nameof(Client.BaseAddress), "Base address cannot be null");
+        }
+
+        _baseUri = new Uri(Client.BaseAddress, "odata/");
+
+        _context = new Container(_baseUri)
+        {
+            HttpClientFactory = HttpClientFactory
+        };
+
+        _model = CommonEndToEndEdmModel.GetEdmModel();
+        ResetDefaultDataSource();
+    }
+
+    [Theory]
+    [InlineData("$var1")]
+    [InlineData("$$")]
+    [InlineData("$$$")]
+    [InlineData("$$$$")]
+    [InlineData("$")]
+    [InlineData("$orderby")]
+    [InlineData("$filter")]
+    [InlineData("$format")]
+    [InlineData("$top")]
+    [InlineData("$count")]
+    [InlineData("$expand")]
+    [InlineData("$select")]
+    public void PrimaryKeyValueBeginsWithDollarSign(string dollarSignKeyValue)
+    {
+        ResetDefaultDataSource();
+
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        var customer = _context.Customers.Take(1).Single();
+
+        var newLogin = new Login { Username = dollarSignKeyValue };
+
+        _context.AddToLogin(newLogin);
+        _context.SetLink(newLogin, "Customer", customer);
+        _context.AddLink(customer, "Logins", newLogin);
+        _context.SaveChanges();
+
+        // Act & Assert
+        var loginQuery = _context.CreateQuery<Login>("Login").Where(l => l.Username == dollarSignKeyValue).ToArray();
+        Assert.True(newLogin == loginQuery.Single(), "Query result does not equal newly added login with key " + dollarSignKeyValue);
+        Assert.Equal(dollarSignKeyValue, loginQuery[0].Username);
+
+        var customerQuery = _context.Execute<Customer>(new Uri(_baseUri + "Login/" + dollarSignKeyValue + "/Customer")).ToArray();
+        Assert.True(customer == customerQuery.Single(), "Execute query result does not equal associated customer");
+    }
+
+    [Theory]
+    [InlineData(" /")]
+    [InlineData("/ ")]
+    [InlineData("var1/baz")]
+    [InlineData("//var1")]
+    [InlineData("var1//")]
+    public void PrimaryKeyValueContainsForwardSlash(string keyValue)
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        var customer = _context.Customers.Take(1).Single();
+
+        var newLogin = new Login { Username = keyValue };
+
+        // Act
+        _context.AddToLogin(newLogin);
+        _context.SetLink(newLogin, "Customer", customer);
+        _context.AddLink(customer, "Logins", newLogin);
+        _context.SaveChanges();
+
+        var loginQuery = _context.CreateQuery<Login>("Login").Where(l => l.Username == keyValue).ToArray();
+
+        // Assert
+        Assert.Single(loginQuery);
+        Assert.Equal(keyValue, loginQuery[0].Username);
+
+        ResetDefaultDataSource();
+    }
+
+    [Theory]
+    [InlineData("var1 baz")]
+    [InlineData("  var1")]
+    public void PrimaryKeyValueContainsWhitespace(string keyValue)
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        var customer = _context.Customers.Take(1).Single();
+
+        var newLogin = new Login { Username = keyValue };
+
+        // Act
+        _context.AddToLogin(newLogin);
+        _context.SetLink(newLogin, "Customer", customer);
+        _context.AddLink(customer, "Logins", newLogin);
+        _context.SaveChanges();
+
+        var loginQuery = _context.CreateQuery<Login>("Login").Where(l => l.Username == keyValue).ToArray();
+        Assert.True(newLogin == loginQuery.Single(), "Query result does not equal newly added login with key " + keyValue);
+
+        var customerQuery = _context.Execute<Customer>(new Uri(_baseUri + "Login/" + keyValue + "/Customer")).ToArray();
+        Assert.True(customer == customerQuery.Single(), "Execute query result does not equal associated customer");
+
+        ResetDefaultDataSource();
+    }
+
+    #region Private methods
+
+    private void ResetDefaultDataSource()
+    {
+        var actionUri = new Uri(_baseUri + "keyasssegmentliteralformattests/Default.ResetDefaultDataSource", UriKind.Absolute);
+        _context.Execute(actionUri, "POST");
+    }
+
+    #endregion
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/StreamTests.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/StreamTests.cs
new file mode 100644
index 0000000000..6a04c6d26f
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/StreamTests.cs
@@ -0,0 +1,167 @@
+//---------------------------------------------------------------------
+// <copyright file="StreamTests.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.OData;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.OData.Client.E2E.TestCommon;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Default;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+using Microsoft.OData.Edm;
+using Xunit;
+using Car = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Car;
+using CustomerInfo = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.CustomerInfo;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Tests;
+
+public class StreamTests : EndToEndTestBase<StreamTests.TestsStartup>
+{
+    private readonly Uri _baseUri;
+    private readonly Container _context;
+    private readonly IEdmModel _model;
+
+    public class TestsStartup : TestStartupBase
+    {
+        public override void ConfigureServices(IServiceCollection services)
+        {
+            services.ConfigureControllers(typeof(KeyAsSegmentTestsController), typeof(MetadataController));
+
+            services.AddControllers().AddOData(opt =>
+                opt.EnableQueryFeatures().AddRouteComponents("odata", CommonEndToEndEdmModel.GetEdmModel()));
+        }
+    }
+
+    public StreamTests(TestWebApplicationFactory<TestsStartup> fixture) : base(fixture)
+    {
+        if (Client.BaseAddress == null)
+        {
+            throw new ArgumentNullException(nameof(Client.BaseAddress), "Base address cannot be null");
+        }
+
+        _baseUri = new Uri(Client.BaseAddress, "odata/");
+
+        _context = new Container(_baseUri)
+        {
+            HttpClientFactory = HttpClientFactory
+        };
+
+        _model = CommonEndToEndEdmModel.GetEdmModel();
+        ResetDefaultDataSource();
+    }
+
+    [Fact]
+    public void GetReadStreamFromMle()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var customerInfoQuery = _context.CreateQuery<CustomerInfo>("CustomerInfos");
+
+        foreach (var customerInfo in customerInfoQuery)
+        {
+            var streamResponse = _context.GetReadStream(customerInfo);
+            Assert.NotNull(streamResponse);
+            using (var reader = new StreamReader(streamResponse.Stream))
+            {
+                var response = reader.ReadToEnd();
+                Assert.NotNull(response);
+            }
+        }
+    }
+
+    [Fact]
+    public void GetReadStreamUriFromMle()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+
+        var customerInfoQuery = _context.CreateQuery<CustomerInfo>("CustomerInfos");
+
+        foreach (var customerInfo in customerInfoQuery)
+        {
+            var streamResponseUri = _context.GetReadStreamUri(customerInfo);
+            Assert.NotNull(streamResponseUri);
+
+            var query = _context.CreateQuery<CustomerInfo>("CustomerInfos").ByKey(customerInfo.CustomerInfoId);
+
+            Assert.False(query.RequestUri.AbsoluteUri.Contains('('), "Uri contains left parentheses");
+            Assert.False(query.RequestUri.AbsoluteUri.Contains(')'), "Uri contains right parentheses");
+            Assert.EndsWith($"odata/CustomerInfos/{customerInfo.CustomerInfoId}", query.RequestUri.AbsoluteUri);
+        }
+    }
+
+    [Fact]
+    public void GetReadStreamFromNamedStreamProperty()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+
+        var firstCar = _context.CreateQuery<Car>("Cars").Take(1).Single();
+
+        var streamResponse = _context.GetReadStream(firstCar, "Photo", new DataServiceRequestArgs());
+
+        // VerifyStreamReadable
+        using (var reader = new StreamReader(streamResponse.Stream))
+        {
+            var photo = reader.ReadToEnd();
+            Assert.NotNull(photo);
+        }
+    }
+
+    [Fact]
+    public void SetSaveStreamOnMle()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+
+        byte[] binaryTestData = new byte[] { 0x00, 0x01, 0x02, 0x03, 0x04, 0x05, 0x06, 0x07, 0x08, 0x09, 0x0a, 0x0b, 0x0c, 0x0d, 0x0e, 0x0f };
+        var memoryStream = new MemoryStream(binaryTestData);
+
+        var customerInfo = _context.CustomerInfos.Take(1).Single();
+
+        // Act
+        _context.SetSaveStream(customerInfo, memoryStream, true, "application/binary", "var1");
+        var dataServiceResponse = _context.SaveChanges();
+        var response = dataServiceResponse.SingleOrDefault() as ChangeOperationResponse;
+
+        // Assert
+        Assert.NotNull(response);
+        Assert.Equal(204, response.StatusCode);
+    }
+
+    [Fact]
+    public void SetSaveStreamOnNamedStreamProperty()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+
+        byte[] binaryTestData = new byte[] { 0x00, 0x01, 0x02, 0x03, 0x04, 0x05, 0x06, 0x07, 0x08, 0x09, 0x0a, 0x0b, 0x0c, 0x0d, 0x0e, 0x0f };
+        var memoryStream = new MemoryStream(binaryTestData);
+
+        // Act
+        var firstCar = _context.CreateQuery<Car>("Cars").Take(1).Single();
+
+        _context.SetSaveStream(firstCar, "Video", memoryStream, true, new DataServiceRequestArgs { ContentType = "application/binary" });
+        var dataServiceResponse = _context.SaveChanges();
+        var response = dataServiceResponse.SingleOrDefault() as ChangeOperationResponse;
+
+        // Assert
+        Assert.NotNull(response);
+        Assert.Equal(204, response.StatusCode);
+        Assert.IsType<StreamDescriptor>(response.Descriptor);
+    }
+
+    #region Private methods
+
+    private void ResetDefaultDataSource()
+    {
+        var actionUri = new Uri(_baseUri + "keyassegmenttests/Default.ResetDefaultDataSource", UriKind.Absolute);
+        _context.Execute(actionUri, "POST");
+    }
+
+    #endregion
+}
diff --git a/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/UpdateTests.cs b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/UpdateTests.cs
new file mode 100644
index 0000000000..096e653691
--- /dev/null
+++ b/test/EndToEndTests/Tests/Client/Microsoft.OData.Client.E2E.Tests/KeyAsSegmentTests/Tests/UpdateTests.cs
@@ -0,0 +1,249 @@
+//---------------------------------------------------------------------
+// <copyright file="UpdateTests.cs" company="Microsoft">
+//      Copyright (C) Microsoft Corporation. All rights reserved. See License.txt in the project root for license information.
+// </copyright>
+//---------------------------------------------------------------------
+
+using Microsoft.AspNetCore.OData;
+using Microsoft.AspNetCore.OData.Batch;
+using Microsoft.AspNetCore.OData.Routing.Controllers;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.OData.Client.E2E.TestCommon;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Default;
+using Microsoft.OData.Client.E2E.Tests.Common.Server.EndToEnd;
+using Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Server;
+using Microsoft.OData.Edm;
+using Xunit;
+using Customer = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Customer;
+using Employee = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Employee;
+using Order = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Order;
+using Person = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.Person;
+using SpecialEmployee = Microsoft.OData.Client.E2E.Tests.Common.Clients.EndToEnd.SpecialEmployee;
+
+namespace Microsoft.OData.Client.E2E.Tests.KeyAsSegmentTests.Tests;
+
+public class UpdateTests : EndToEndTestBase<UpdateTests.TestsStartup>
+{
+    private readonly Uri _baseUri;
+    private readonly Container _context;
+    private readonly IEdmModel _model;
+
+    public class TestsStartup : TestStartupBase
+    {
+        public override void ConfigureServices(IServiceCollection services)
+        {
+            services.ConfigureControllers(typeof(UpdateTestsController), typeof(MetadataController));
+
+            services.AddControllers().AddOData(opt =>
+                opt.EnableQueryFeatures().AddRouteComponents("odata", CommonEndToEndEdmModel.GetEdmModel(), batchHandler: new DefaultODataBatchHandler()));
+        }
+    }
+
+    public UpdateTests(TestWebApplicationFactory<TestsStartup> fixture) : base(fixture)
+    {
+        if (Client.BaseAddress == null)
+        {
+            throw new ArgumentNullException(nameof(Client.BaseAddress), "Base address cannot be null");
+        }
+
+        _baseUri = new Uri(Client.BaseAddress, "odata/");
+
+        _context = new Container(_baseUri)
+        {
+            HttpClientFactory = HttpClientFactory
+        };
+
+        _model = CommonEndToEndEdmModel.GetEdmModel();
+        ResetDefaultDataSource();
+    }
+
+    [Fact]
+    public void InsertSave()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var newPerson = new Person { PersonId = 9999, Name = "Some Person" };
+        var personQuery = _context.People.Where(p => p.PersonId == newPerson.PersonId);
+
+        _context.IgnoreResourceNotFoundException = true;
+
+        // Act & Assert
+        var retrievedPerson = personQuery.SingleOrDefault();
+        Assert.Null(retrievedPerson);
+
+        _context.AddObject("People", newPerson);
+        _context.SaveChanges();
+
+        retrievedPerson = personQuery.SingleOrDefault();
+        Assert.NotNull(retrievedPerson);
+        Assert.True(newPerson == retrievedPerson, "New entity and retrieved entity should reference same object");
+    }
+
+    [Fact]
+    public void AttachUpdateObjectSave()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var specialEmployee = new SpecialEmployee { PersonId = -10 };
+        _context.AttachTo("People", specialEmployee);
+
+        specialEmployee.Bonus = Int32.MaxValue;
+        _context.UpdateObject(specialEmployee);
+        _context.SaveChanges();
+
+        var retrievedPerson = _context.People.ByKey(specialEmployee.PersonId).GetValue();
+        var retrievedBonus = (retrievedPerson as SpecialEmployee)?.Bonus;
+        Assert.Equal(Int32.MaxValue, retrievedBonus);
+    }
+
+    [Fact]
+    public void AddObjectSave()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        var specialEmployee = new SpecialEmployee { PersonId = 1234 };
+
+        // Act & Assert
+        _context.AddObject("People", specialEmployee);
+        var savedResponse = _context.SaveChanges();
+        Assert.Equal(201, (savedResponse.Single() as ChangeOperationResponse)?.StatusCode);
+        Assert.NotNull(_context.People.ByKey(1234).GetValue());
+
+        _context.DeleteObject(specialEmployee);
+        var deletedResponse = _context.SaveChanges();
+        Assert.Equal(204, (deletedResponse.Single() as ChangeOperationResponse)?.StatusCode);
+        var exception = Record.Exception(() => _context.People.ByKey(1234).GetValue());
+        Assert.NotNull(exception);
+        Assert.Equal("NotFound", exception.InnerException?.Message);
+    }
+
+    [Fact]
+    public void AddObjectAddRelatedObjectSave()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        var customer = new Customer { CustomerId = 1234 };
+        var order = new Order { OrderId = 12345 };
+
+        // Act
+        _context.AddObject("Customers", customer);
+        _context.AddRelatedObject(customer, "Orders", order);
+        var savedChangesResponse = _context.SaveChanges();
+
+        // Assert
+        Assert.True(savedChangesResponse.All(s => s.StatusCode == 201));
+        var customerSaved = _context.Customers.ByKey(1234).Expand(c => c.Orders).GetValue();
+        Assert.NotNull(customerSaved);
+        Assert.Equal(1234, customerSaved.CustomerId);
+        Assert.Contains(customerSaved.Orders, o => o.OrderId == 12345);
+    }
+
+    [Fact]
+    public void AddDeleteLinkSave()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        var customer = _context.Customers.Expand(c => c.Orders).First();
+        var order = _context.Orders.ToArray().Except(customer.Orders).First();
+
+        // Act & Assert
+        _context.AddLink(customer, "Orders", order);
+        _context.SaveChanges();
+
+        // Order exists in customer's orders
+        var customerWithOrders = _context.Customers.ByKey(customer.CustomerId).Expand(c => c.Orders).GetValue();
+        Assert.Contains(customerWithOrders.Orders, o => o.OrderId == order.OrderId);
+
+        _context.DeleteLink(customer, "Orders", order);
+        _context.SaveChanges();
+
+        // Order does not exist in customer's orders
+        var customerWithoutOrders = _context.Customers.ByKey(customer.CustomerId).Expand(c => c.Orders).GetValue();
+        Assert.DoesNotContain(customerWithoutOrders.Orders, o => o.OrderId == order.OrderId);
+    }
+
+    [Fact]
+    public void AddDeleteLinkSaveBatch()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        var customer = _context.Customers.Expand(c => c.Orders).First();
+        var order1 = _context.Orders.ToArray().Except(customer.Orders).First();
+        var order2 = _context.Orders.OrderByDescending(o => o.OrderId).ToArray().Except(customer.Orders).First();
+
+        // Act & Assert
+        _context.AddLink(customer, "Orders", order1);
+        _context.AddLink(customer, "Orders", order2);
+
+        _context.SaveChanges(SaveChangesOptions.BatchWithSingleChangeset);
+
+        // Order exists in customer's orders
+        var customerWithoutOrders = _context.Customers.ByKey(customer.CustomerId).Expand(c => c.Orders).GetValue();
+        Assert.Contains(customerWithoutOrders.Orders, o => o.OrderId == order1.OrderId || o.OrderId == order2.OrderId);
+
+        _context.DeleteLink(customer, "Orders", order1);
+        _context.DeleteLink(customer, "Orders", order2);
+        _context.SaveChanges(SaveChangesOptions.BatchWithSingleChangeset);
+
+        // Order does not exist in customer's orders
+        var customerWithOrders = _context.Customers.ByKey(customer.CustomerId).Expand(c => c.Orders).GetValue();
+        Assert.DoesNotContain(customerWithOrders.Orders, o => o.OrderId == order1.OrderId || o.OrderId == order2.OrderId);
+    }
+
+    [Fact]
+    public void SetLinkSave()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        // Act & Assert
+        var employee = _context.People.OfType<Employee>().First();
+
+        _context.SetLink(employee, "Manager", employee);
+        _context.SaveChanges();
+
+        var employeeWithManager = (_context.People.OfType<Employee>().Where(s => s.PersonId == employee.PersonId) as DataServiceQuery<Employee>)?.Expand(e => e.Manager).Single();
+        Assert.NotNull(employeeWithManager?.Manager);
+        Assert.Equal(employee.PersonId, employeeWithManager.Manager.PersonId);
+    }
+
+    [Fact]
+    public void AddRelatedObjectSave()
+    {
+        // Arrange
+        _context.UrlKeyDelimiter = DataServiceUrlKeyDelimiter.Slash;
+        _context.MergeOption = MergeOption.PreserveChanges;
+
+        // Act
+        var customer = _context.Customers.First();
+        var order = new Order { OrderId = 1234 };
+
+        _context.AddRelatedObject(customer, "Orders", order);
+        var savedChangeResponse = _context.SaveChanges();
+
+        // Assert
+        var response = savedChangeResponse.Single() as ChangeOperationResponse;
+        Assert.Equal(201, response?.StatusCode);
+
+        var entity = response?.Descriptor as EntityDescriptor;
+        Assert.EndsWith("/Orders(1234)", entity?.EditLink.OriginalString);
+    }
+
+    #region Private methods
+
+    private void ResetDefaultDataSource()
+    {
+        var actionUri = new Uri(_baseUri + "keyassegmentupdatetests/Default.ResetDefaultDataSource", UriKind.Absolute);
+        _context.Execute(actionUri, "POST");
+    }
+
+    #endregion
+}