diff --git a/src/Analyzers/Analyzers/src/UseAuthorizationAnalyzer.cs b/src/Analyzers/Analyzers/src/UseAuthorizationAnalyzer.cs
index 6d790ddb47..dbfa9a3dcb 100644
--- a/src/Analyzers/Analyzers/src/UseAuthorizationAnalyzer.cs
+++ b/src/Analyzers/Analyzers/src/UseAuthorizationAnalyzer.cs
@@ -2,6 +2,7 @@
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
 
 using System.Diagnostics;
+using System.Linq;
 using Microsoft.CodeAnalysis;
 using Microsoft.CodeAnalysis.Diagnostics;
 
@@ -27,6 +28,7 @@ namespace Microsoft.AspNetCore.Analyzers
             {
                 MiddlewareItem? useAuthorizationItem = default;
                 MiddlewareItem? useRoutingItem = default;
+                MiddlewareItem? useEndpoint = default;
 
                 var length = middlewareAnalysis.Middleware.Length;
                 for (var i = length - 1; i >= 0; i-- )
@@ -70,9 +72,24 @@ namespace Microsoft.AspNetCore.Analyzers
                                 useAuthorizationItem.Operation.Syntax.GetLocation(),
                                 middlewareItem.UseMethod.Name));
                         }
+
+                        useEndpoint = middlewareItem;
                     }
                     else if (middleware == "UseRouting")
                     {
+                        if (useEndpoint is null)
+                        {
+                            // We're likely here because the middleware uses an expression chain e.g.
+                            // app.UseRouting()
+                            //   .UseAuthorization()
+                            //   .UseEndpoints(..));
+                            // This analyzer expects MiddlewareItem instances to appear in the order in which they appear in source
+                            // which unfortunately isn't true for chained calls (the operations appear in reverse order).
+                            // We'll avoid doing any analysis in this event and rely on the runtime guardrails.
+                            // We'll use https://github.com/aspnet/AspNetCore/issues/16648 to track addressing this in a future milestone
+                            return;
+                        }
+
                         useRoutingItem = middlewareItem;
                     }
                 }
diff --git a/src/Analyzers/Analyzers/test/StartupAnalyzerTest.cs b/src/Analyzers/Analyzers/test/StartupAnalyzerTest.cs
index 00877ee2d3..fc635ef7f2 100644
--- a/src/Analyzers/Analyzers/test/StartupAnalyzerTest.cs
+++ b/src/Analyzers/Analyzers/test/StartupAnalyzerTest.cs
@@ -244,6 +244,22 @@ namespace Microsoft.AspNetCore.Analyzers
             Assert.Empty(diagnostics);
         }
 
+        [Fact]
+        public async Task StartupAnalyzer_UseAuthorizationConfiguredAsAChain_ReportsNoDiagnostics()
+        {
+            // Regression test for https://github.com/aspnet/AspNetCore/issues/15203
+            // Arrange
+            var source = Read(nameof(TestFiles.StartupAnalyzerTest.UseAuthConfiguredCorrectlyChained));
+
+            // Act
+            var diagnostics = await Runner.GetDiagnosticsAsync(source.Source);
+
+            // Assert
+            var middlewareAnalysis = Assert.Single(Analyses.OfType<MiddlewareAnalysis>());
+            Assert.NotEmpty(middlewareAnalysis.Middleware);
+            Assert.Empty(diagnostics);
+        }
+
         [Fact]
         public async Task StartupAnalyzer_UseAuthorizationInvokedMultipleTimesInEndpointRoutingBlock_ReportsNoDiagnostics()
         {
@@ -279,6 +295,23 @@ namespace Microsoft.AspNetCore.Analyzers
                 });
         }
 
+        [Fact]
+        public async Task StartupAnalyzer_UseAuthorizationConfiguredBeforeUseRoutingChained_ReportsDiagnostics()
+        {
+            // This one asserts a false negative for https://github.com/aspnet/AspNetCore/issues/15203.
+            // We don't correctly identify chained calls, this test verifies the behavior.
+            // Arrange
+            var source = Read(nameof(TestFiles.StartupAnalyzerTest.UseAuthBeforeUseRoutingChained));
+
+            // Act
+            var diagnostics = await Runner.GetDiagnosticsAsync(source.Source);
+
+            // Assert
+            var middlewareAnalysis = Assert.Single(Analyses.OfType<MiddlewareAnalysis>());
+            Assert.NotEmpty(middlewareAnalysis.Middleware);
+            Assert.Empty(diagnostics);
+        }
+
         [Fact]
         public async Task StartupAnalyzer_UseAuthorizationConfiguredAfterUseEndpoints_ReportsDiagnostics()
         {
diff --git a/src/Analyzers/Analyzers/test/TestFiles/StartupAnalyzerTest/UseAuthBeforeUseRoutingChained.cs b/src/Analyzers/Analyzers/test/TestFiles/StartupAnalyzerTest/UseAuthBeforeUseRoutingChained.cs
new file mode 100644
index 0000000000..d76ecd0997
--- /dev/null
+++ b/src/Analyzers/Analyzers/test/TestFiles/StartupAnalyzerTest/UseAuthBeforeUseRoutingChained.cs
@@ -0,0 +1,17 @@
+// Copyright (c) .NET Foundation. All rights reserved.
+// Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
+
+using Microsoft.AspNetCore.Builder;
+
+namespace Microsoft.AspNetCore.Analyzers.TestFiles.StartupAnalyzerTest {
+    public class UseAuthBeforeUseRoutingChained
+    {
+        public void Configure(IApplicationBuilder app)
+        {
+            app.UseFileServer()
+               .UseAuthorization()
+               .UseRouting()
+               .UseEndpoints(r => { });
+        }
+    }
+}
diff --git a/src/Analyzers/Analyzers/test/TestFiles/StartupAnalyzerTest/UseAuthConfiguredCorrectlyChained.cs b/src/Analyzers/Analyzers/test/TestFiles/StartupAnalyzerTest/UseAuthConfiguredCorrectlyChained.cs
new file mode 100644
index 0000000000..c7d170e750
--- /dev/null
+++ b/src/Analyzers/Analyzers/test/TestFiles/StartupAnalyzerTest/UseAuthConfiguredCorrectlyChained.cs
@@ -0,0 +1,16 @@
+// Copyright (c) .NET Foundation. All rights reserved.
+// Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
+
+using Microsoft.AspNetCore.Builder;
+
+namespace Microsoft.AspNetCore.Analyzers.TestFiles.StartupAnalyzerTest {
+    public class UseAuthConfiguredCorrectlyChained
+    {
+        public void Configure(IApplicationBuilder app)
+        {
+            app.UseRouting()
+               .UseAuthorization()
+               .UseEndpoints(r => { });
+        }
+    }
+}