diff --git a/tracer/src/Datadog.Trace.Trimming/build/Datadog.Trace.Trimming.xml b/tracer/src/Datadog.Trace.Trimming/build/Datadog.Trace.Trimming.xml
index e252c1c8ac5b..e3491cc9cace 100644
--- a/tracer/src/Datadog.Trace.Trimming/build/Datadog.Trace.Trimming.xml
+++ b/tracer/src/Datadog.Trace.Trimming/build/Datadog.Trace.Trimming.xml
@@ -48,12 +48,10 @@
    </assembly>
    <assembly fullname="Microsoft.AspNetCore.Http.Features">
       <type fullname="Microsoft.AspNetCore.Http.Features.IFeatureCollection" />
-      <type fullname="Microsoft.AspNetCore.Http.Features.ISessionFeature" />
       <type fullname="Microsoft.AspNetCore.Http.IHeaderDictionary" />
       <type fullname="Microsoft.AspNetCore.Http.IQueryCollection" />
       <type fullname="Microsoft.AspNetCore.Http.IRequestCookieCollection" />
       <type fullname="Microsoft.AspNetCore.Http.IResponseCookies" />
-      <type fullname="Microsoft.AspNetCore.Http.ISession" />
    </assembly>
    <assembly fullname="Microsoft.AspNetCore.Identity" />
    <assembly fullname="Microsoft.AspNetCore.Mvc.Abstractions">
diff --git a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs
index 7df6633754ff..8383184bfa0f 100644
--- a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs
+++ b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs
@@ -16,7 +16,6 @@
 using Datadog.Trace.Util.Http;
 using Datadog.Trace.Vendors.Serilog.Events;
 using Microsoft.AspNetCore.Http;
-using Microsoft.AspNetCore.Http.Features;
 using Microsoft.AspNetCore.Routing;
 using Microsoft.Extensions.Primitives;
 
diff --git a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinatorHelpers.Core.cs b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinatorHelpers.Core.cs
index f0f7c2659912..523af9c3ddaf 100644
--- a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinatorHelpers.Core.cs
+++ b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinatorHelpers.Core.cs
@@ -7,10 +7,11 @@
 #if !NETFRAMEWORK
 using System;
 using System.Collections.Generic;
+using System.Reflection;
 using Datadog.Trace.AppSec.Waf;
+using Datadog.Trace.DuckTyping;
 using Datadog.Trace.Logging;
 using Microsoft.AspNetCore.Http;
-using Microsoft.AspNetCore.Http.Features;
 using Microsoft.AspNetCore.Mvc.Abstractions;
 using Microsoft.AspNetCore.Routing;
 
@@ -20,6 +21,8 @@ internal static class SecurityCoordinatorHelpers
 {
     private static readonly IDatadogLogger Log = DatadogLogging.GetLoggerFor(typeof(SecurityCoordinatorHelpers));
 
+    internal static readonly Type? SessionFeature = Assembly.GetAssembly(typeof(IHeaderDictionary))?.GetType("Microsoft.AspNetCore.Http.Features.ISessionFeature", throwOnError: false);
+
     internal static void CheckAndBlock(this Security security, HttpContext context, Span span)
     {
         if (security.AppsecEnabled)
@@ -82,9 +85,16 @@ internal static void CheckPathParamsAndSessionId(this Security security, HttpCon
                 var args = new Dictionary<string, object> { { AddressesConstants.RequestPathParams, pathParams } };
                 IResult? result;
                 // we need to check context.Features.Get<ISessionFeature> as accessing the Session item if session has not been configured for the application is throwing InvalidOperationException
-                if (context.Features.Get<ISessionFeature>() is { Session.IsAvailable: true } feature)
+                var sessionFeature = context.Features[SessionFeature];
+                Datadog.Trace.ClrProfiler.AutoInstrumentation.AspNetCore.UserEvents.ISessionFeature? sessionFeatureProxy = null;
+                if (sessionFeature is not null)
+                {
+                    sessionFeatureProxy = sessionFeature.DuckCast<ClrProfiler.AutoInstrumentation.AspNetCore.UserEvents.ISessionFeature>();
+                }
+
+                if (sessionFeatureProxy?.Session?.IsAvailable == true)
                 {
-                    result = securityCoordinator.RunWaf(args, sessionId: feature.Session.Id);
+                    result = securityCoordinator.RunWaf(args, sessionId: sessionFeatureProxy.Session.Id);
                 }
                 else
                 {
diff --git a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/HttpContextSetUser.cs b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/HttpContextSetUser.cs
index b2d69da601ed..3195217bf403 100644
--- a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/HttpContextSetUser.cs
+++ b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/HttpContextSetUser.cs
@@ -13,6 +13,7 @@
 using Datadog.Trace.AppSec.Coordinator;
 using Datadog.Trace.ClrProfiler.CallTarget;
 using Datadog.Trace.Configuration;
+using Datadog.Trace.DuckTyping;
 using Microsoft.AspNetCore.Http;
 using Microsoft.AspNetCore.Http.Features;
 
@@ -90,8 +91,15 @@ internal static CallTargetState OnMethodBegin<TTarget>(TTarget instance, ref Cla
                         }
                     }
 
-                    var sessionId = httpContext.Features.Get<ISessionFeature>()?.Session?.Id;
-                    var result = secCoord.RunWafForUser(userSessionId: sessionId, userId: userId);
+                    ISessionFeature? sessionFeatureProxy = null;
+                    var sessionFeature = httpContext.Features[SecurityCoordinatorHelpers.SessionFeature];
+
+                    if (sessionFeature is not null)
+                    {
+                        sessionFeatureProxy = sessionFeature.DuckCast<ISessionFeature>();
+                    }
+
+                    var result = secCoord.RunWafForUser(userSessionId: sessionFeatureProxy?.Session?.Id, userId: userId);
                     secCoord.BlockAndReport(result);
 
                     UserEventsCommon.RecordMetricsLoginSuccessIfNotFound(foundUserId, true);
diff --git a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/ISession.cs b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/ISession.cs
new file mode 100644
index 000000000000..c501379b47d5
--- /dev/null
+++ b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/ISession.cs
@@ -0,0 +1,29 @@
+// <copyright file="ISession.cs" company="Datadog">
+// Unless explicitly stated otherwise all files in this repository are licensed under the Apache 2 License.
+// This product includes software developed at Datadog (https://www.datadoghq.com/). Copyright 2017 Datadog, Inc.
+// </copyright>
+
+#if !NETFRAMEWORK
+#nullable enable
+using System.ComponentModel;
+
+namespace Datadog.Trace.ClrProfiler.AutoInstrumentation.AspNetCore.UserEvents;
+
+/// <summary>
+/// Duck type of the SignInManager aspnet core type
+/// </summary>
+[Browsable(false)]
+[EditorBrowsable(EditorBrowsableState.Never)]
+public interface ISession
+{
+    /// <summary>
+    /// Gets a value indicating whether the session is available
+    /// </summary>
+    bool IsAvailable { get; }
+
+    /// <summary>
+    /// Gets the session id
+    /// </summary>
+    string Id { get; }
+}
+#endif
diff --git a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/ISessionFeature.cs b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/ISessionFeature.cs
new file mode 100644
index 000000000000..afb8ddc8d880
--- /dev/null
+++ b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/AspNetCore/UserEvents/ISessionFeature.cs
@@ -0,0 +1,24 @@
+// <copyright file="ISessionFeature.cs" company="Datadog">
+// Unless explicitly stated otherwise all files in this repository are licensed under the Apache 2 License.
+// This product includes software developed at Datadog (https://www.datadoghq.com/). Copyright 2017 Datadog, Inc.
+// </copyright>
+
+#if !NETFRAMEWORK
+#nullable enable
+using System.ComponentModel;
+
+namespace Datadog.Trace.ClrProfiler.AutoInstrumentation.AspNetCore.UserEvents;
+
+/// <summary>
+/// Duck type of the ISessionFeature aspnet core type in Microsoft.AspNetCore.Http.Features assembly
+/// </summary>
+[Browsable(false)]
+[EditorBrowsable(EditorBrowsableState.Never)]
+public interface ISessionFeature
+{
+    /// <summary>
+    /// Gets the Session object, can be null
+    /// </summary>
+    public ISession Session { get; }
+}
+#endif
diff --git a/tracer/test/test-applications/security/Samples.Security.AspNetCore5/Controllers/SessionController.cs b/tracer/test/test-applications/security/Samples.Security.AspNetCore5/Controllers/SessionController.cs
new file mode 100644
index 000000000000..096e17f75ae1
--- /dev/null
+++ b/tracer/test/test-applications/security/Samples.Security.AspNetCore5/Controllers/SessionController.cs
@@ -0,0 +1,34 @@
+using System;
+using Microsoft.AspNetCore.Mvc;
+using Microsoft.AspNetCore.Mvc.Formatters;
+using Microsoft.AspNetCore.Mvc.ModelBinding;
+using Microsoft.AspNetCore.Mvc.ModelBinding.Binders;
+using Microsoft.AspNetCore.Routing;
+using System.Collections.Generic;
+using System.Threading.Tasks;
+using Datadog.Trace;
+
+namespace weblog
+{
+    [ApiController]
+    [Route("session")]
+    public class SessionController : Controller
+    {
+	    [HttpGet("new")]
+        public IActionResult New()
+        {
+            return Content(HttpContext.Session.Id);
+        }
+
+        [HttpGet("user")]
+        public IActionResult User(string sdk_user)
+        {
+            if (sdk_user != null)
+            {
+                Samples.SampleHelpers.TrackUserLoginSuccessEvent(sdk_user, null);
+            }
+
+            return Content($"Hello, set the user to {sdk_user}");
+        }
+    }
+}