diff --git a/src/Microsoft.Identity.Web.Sidecar/Configuration/SidecarOptions.cs b/src/Microsoft.Identity.Web.Sidecar/Configuration/SidecarOptions.cs
index 98d35646d..dd9cda737 100644
--- a/src/Microsoft.Identity.Web.Sidecar/Configuration/SidecarOptions.cs
+++ b/src/Microsoft.Identity.Web.Sidecar/Configuration/SidecarOptions.cs
@@ -16,6 +16,13 @@ public class SidecarOptions
     /// ignored on that route and a warning is logged.
     /// </summary>
     public AllowOverridesOptions AllowOverrides { get; set; } = new();
+
+    /// <summary>
+    /// Gets or sets a value indicating whether the sidecar's outbound
+    /// <see cref="System.Net.Http.HttpClient"/> follows HTTP redirect (3xx) responses
+    /// from downstream APIs. Defaults to <c>false</c>.
+    /// </summary>
+    public bool AllowOutboundRedirects { get; set; }
 }
 
 /// <summary>
diff --git a/src/Microsoft.Identity.Web.Sidecar/Program.cs b/src/Microsoft.Identity.Web.Sidecar/Program.cs
index 8787654a4..7fad0e589 100644
--- a/src/Microsoft.Identity.Web.Sidecar/Program.cs
+++ b/src/Microsoft.Identity.Web.Sidecar/Program.cs
@@ -4,6 +4,7 @@
 using System.Diagnostics.CodeAnalysis;
 using System.IdentityModel.Tokens.Jwt;
 using Microsoft.AspNetCore.Authentication.JwtBearer;
+using Microsoft.Extensions.Options;
 using Microsoft.Identity.Web.Sidecar.Configuration;
 using Microsoft.Identity.Web.Sidecar.Endpoints;
 using Microsoft.IdentityModel.JsonWebTokens;
@@ -46,6 +47,14 @@ public static void Main(string[] args)
 
         builder.Services.Configure<SidecarOptions>(builder.Configuration.GetSection("Sidecar"));
 
+        builder.Services.ConfigureHttpClientDefaults(http =>
+            http.ConfigurePrimaryHttpMessageHandler(serviceProvider =>
+                new SocketsHttpHandler
+                {
+                    AllowAutoRedirect = serviceProvider.GetRequiredService<IOptions<SidecarOptions>>()
+                        .Value.AllowOutboundRedirects,
+                }));
+
         builder.Services.AddHealthChecks();
 
         ConfigureAuthN(builder);
diff --git a/src/Microsoft.Identity.Web.Sidecar/README.md b/src/Microsoft.Identity.Web.Sidecar/README.md
index 4b621911b..b1996f31c 100644
--- a/src/Microsoft.Identity.Web.Sidecar/README.md
+++ b/src/Microsoft.Identity.Web.Sidecar/README.md
@@ -48,6 +48,24 @@ Settings are supplied via `appsettings.json`, environment variables, or any stan
 - **AzureAd**: Standard Microsoft.Identity.Web web API registration; client credentials are optional if only delegated flows are required.
 - **DownstreamApis**: Named profiles for endpoints resolved via `{apiName}`.
 
+### Outbound redirects
+
+`Sidecar:AllowOutboundRedirects` controls whether the sidecar's outbound `HttpClient`
+follows HTTP redirect (3xx) responses returned by a downstream API. It defaults to
+`false`, so a redirect response is returned to the caller as-is rather than followed.
+Set it to `true` to opt in to following redirects.
+
+> **Note:** Outbound redirects are not followed by default (`AllowOutboundRedirects`
+> defaults to `false`). To follow redirects, set it to `true`:
+>
+> ```jsonc
+> {
+>   "Sidecar": {
+>     "AllowOutboundRedirects": true
+>   }
+> }
+> ```
+
 ## Running the sidecar
 
 ### Prerequisites
diff --git a/tests/E2E Tests/Sidecar.Tests/OutboundRedirectTests.cs b/tests/E2E Tests/Sidecar.Tests/OutboundRedirectTests.cs
new file mode 100644
index 000000000..580eb2be4
--- /dev/null
+++ b/tests/E2E Tests/Sidecar.Tests/OutboundRedirectTests.cs	
@@ -0,0 +1,237 @@
+// Copyright (c) Microsoft Corporation. All rights reserved.
+// Licensed under the MIT License.
+
+using System.Net;
+using System.Net.Http.Json;
+using System.Net.Sockets;
+using System.Security.Claims;
+using System.Text;
+using Microsoft.AspNetCore.Authentication;
+using Microsoft.AspNetCore.Authentication.JwtBearer;
+using Microsoft.Extensions.Configuration;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Extensions.Options;
+using Microsoft.Identity.Abstractions;
+using Microsoft.Identity.Web.Sidecar.Models;
+using Moq;
+using Xunit;
+
+namespace Sidecar.Tests;
+
+public class OutboundRedirectTests
+{
+    [Fact]
+    public async Task OutboundRedirect_NotFollowedByDefault_ReturnsRedirectAndTargetNotContacted()
+    {
+        // Arrange
+        const string apiName = "redirect-api";
+
+        using var redirectTarget = new RawHttpServer(_ =>
+            "HTTP/1.1 200 OK\r\nContent-Length: 2\r\nConnection: close\r\n\r\nOK");
+        string redirectTargetUrl = $"http://127.0.0.1:{redirectTarget.Port}/next";
+
+        using var configured = new RawHttpServer(_ =>
+            $"HTTP/1.1 302 Found\r\nLocation: {redirectTargetUrl}\r\nContent-Length: 0\r\nConnection: close\r\n\r\n");
+
+        var headerProvider = CreateHeaderProviderMock();
+
+        using var factory = new SidecarApiFactory();
+        var client = factory.WithWebHostBuilder(builder =>
+        {
+            builder.ConfigureServices(services =>
+            {
+                services.AddSingleton(headerProvider.Object);
+                services.Configure<DownstreamApiOptions>(apiName, o =>
+                {
+                    o.BaseUrl = $"http://127.0.0.1:{configured.Port}";
+                    o.RelativePath = "/start";
+                    o.HttpMethod = HttpMethod.Get.Method;
+                    o.RequestAppToken = true;
+                    o.Scopes = ["api.default"];
+                });
+            });
+        }).CreateClient();
+
+        // Act
+        var response = await client.PostAsync($"/DownstreamApiUnauthenticated/{apiName}", content: null);
+        var body = await response.Content.ReadFromJsonAsync<DownstreamApiResult>();
+
+        // Assert
+        Assert.Equal(HttpStatusCode.OK, response.StatusCode);
+        Assert.NotNull(body);
+        Assert.Equal(302, body!.StatusCode);
+        Assert.True(configured.HitCount >= 1);
+        Assert.Equal(0, redirectTarget.HitCount);
+    }
+
+    [Fact]
+    public async Task OutboundRedirect_FollowedWhenOptedIn_TargetContacted()
+    {
+        // Arrange
+        const string apiName = "redirect-api";
+
+        using var redirectTarget = new RawHttpServer(_ =>
+            "HTTP/1.1 200 OK\r\nContent-Length: 2\r\nConnection: close\r\n\r\nOK");
+        string redirectTargetUrl = $"http://127.0.0.1:{redirectTarget.Port}/next";
+
+        using var configured = new RawHttpServer(_ =>
+            $"HTTP/1.1 302 Found\r\nLocation: {redirectTargetUrl}\r\nContent-Length: 0\r\nConnection: close\r\n\r\n");
+
+        var headerProvider = CreateHeaderProviderMock();
+
+        using var factory = new SidecarApiFactory();
+        var client = factory.WithWebHostBuilder(builder =>
+        {
+            builder.ConfigureAppConfiguration((_, config) =>
+            {
+                config.AddInMemoryCollection(new Dictionary<string, string?>
+                {
+                    { "Sidecar:AllowOutboundRedirects", "true" },
+                });
+            });
+
+            builder.ConfigureServices(services =>
+            {
+                services.AddSingleton(headerProvider.Object);
+                services.Configure<DownstreamApiOptions>(apiName, o =>
+                {
+                    o.BaseUrl = $"http://127.0.0.1:{configured.Port}";
+                    o.RelativePath = "/start";
+                    o.HttpMethod = HttpMethod.Get.Method;
+                    o.RequestAppToken = true;
+                    o.Scopes = ["api.default"];
+                });
+            });
+        }).CreateClient();
+
+        // Act
+        var response = await client.PostAsync($"/DownstreamApiUnauthenticated/{apiName}", content: null);
+        var body = await response.Content.ReadFromJsonAsync<DownstreamApiResult>();
+
+        // Assert
+        Assert.Equal(HttpStatusCode.OK, response.StatusCode);
+        Assert.NotNull(body);
+        Assert.Equal(200, body!.StatusCode);
+        Assert.True(configured.HitCount >= 1);
+        Assert.True(redirectTarget.HitCount >= 1);
+    }
+
+    // Sidecar supports bearer tokens only. To add mTLS, also set AllowAutoRedirect = false
+    // on the mTLS client.
+    [Fact]
+    public async Task Sidecar_DownstreamCalls_UseDefaultHttpClientFactoryPath()
+    {
+        // Arrange
+        const string apiName = "guard-api";
+
+        using var factory = new SidecarApiFactory();
+        using var host = factory.WithWebHostBuilder(builder =>
+        {
+            builder.ConfigureServices(services =>
+            {
+                services.Configure<DownstreamApiOptions>(apiName, o =>
+                {
+                    o.BaseUrl = "https://downstream.example";
+                    o.Scopes = ["api.default"];
+                });
+            });
+        });
+
+        using var scope = host.Services.CreateScope();
+        var provider = scope.ServiceProvider;
+
+        // Act
+        var schemes = (await provider.GetRequiredService<IAuthenticationSchemeProvider>()
+            .GetAllSchemesAsync()).ToList();
+        var defaultScheme = await provider.GetRequiredService<IAuthenticationSchemeProvider>()
+            .GetDefaultAuthenticateSchemeAsync();
+        var options = provider.GetRequiredService<IOptionsMonitor<DownstreamApiOptions>>().Get(apiName);
+
+        // Assert
+        Assert.All(schemes, s => Assert.Equal(JwtBearerDefaults.AuthenticationScheme, s.Name));
+        Assert.Equal(JwtBearerDefaults.AuthenticationScheme, defaultScheme?.Name);
+        Assert.NotEqual("MTLS", options.ProtocolScheme, StringComparer.OrdinalIgnoreCase);
+        Assert.NotEqual("MTLS_POP", options.ProtocolScheme, StringComparer.OrdinalIgnoreCase);
+    }
+
+    private static Mock<IAuthorizationHeaderProvider> CreateHeaderProviderMock()
+    {
+        var mock = new Mock<IAuthorizationHeaderProvider>();
+        mock.Setup(p => p.CreateAuthorizationHeaderAsync(
+                It.IsAny<IEnumerable<string>>(),
+                It.IsAny<AuthorizationHeaderProviderOptions?>(),
+                It.IsAny<ClaimsPrincipal?>(),
+                It.IsAny<CancellationToken>()))
+            .ReturnsAsync("Bearer test-token");
+        return mock;
+    }
+
+    private sealed class RawHttpServer : IDisposable
+    {
+        private readonly TcpListener _listener;
+        private readonly Func<string, string> _responder;
+        private readonly CancellationTokenSource _cts = new();
+        private int _hitCount;
+
+        public RawHttpServer(Func<string, string> responder)
+        {
+            _responder = responder;
+            _listener = new TcpListener(IPAddress.Loopback, 0);
+            _listener.Start();
+            Port = ((IPEndPoint)_listener.LocalEndpoint).Port;
+            _ = Task.Run(AcceptLoopAsync);
+        }
+
+        public int Port { get; }
+
+        public int HitCount => Volatile.Read(ref _hitCount);
+
+        private async Task AcceptLoopAsync()
+        {
+            while (!_cts.IsCancellationRequested)
+            {
+                TcpClient tcp;
+                try
+                {
+                    tcp = await _listener.AcceptTcpClientAsync(_cts.Token);
+                }
+                catch
+                {
+                    break;
+                }
+
+                _ = Task.Run(() => HandleAsync(tcp));
+            }
+        }
+
+        private async Task HandleAsync(TcpClient tcp)
+        {
+            try
+            {
+                using (tcp)
+                await using (var stream = tcp.GetStream())
+                {
+                    var buffer = new byte[8192];
+                    int read = await stream.ReadAsync(buffer);
+                    string requestText = Encoding.ASCII.GetString(buffer, 0, read);
+                    Interlocked.Increment(ref _hitCount);
+
+                    byte[] responseBytes = Encoding.ASCII.GetBytes(_responder(requestText));
+                    await stream.WriteAsync(responseBytes);
+                    await stream.FlushAsync();
+                }
+            }
+            catch
+            {
+                // Best-effort test listener.
+            }
+        }
+
+        public void Dispose()
+        {
+            _cts.Cancel();
+            _listener.Stop();
+            _cts.Dispose();
+        }
+    }
+}