using Microsoft.AspNetCore.Authentication;
using Microsoft.AspNetCore.Authentication.JwtBearer;
using Microsoft.AspNetCore.Authorization;
using Microsoft.AspNetCore.Builder;
using Microsoft.AspNetCore.Http;
using Microsoft.AspNetCore.WebUtilities;
using Microsoft.Extensions.DependencyInjection;
using ModelContextProtocol;
using ModelContextProtocol.AspNetCore.Authentication;
using ModelContextProtocol.Authentication;
using ModelContextProtocol.Client;
using ModelContextProtocol.Protocol;
using ModelContextProtocol.Server;
using System.Net;
using System.Net.Http.Json;
using System.Security.Claims;
using System.Text.Json;
using Xunit.Sdk;

namespace ModelContextProtocol.AspNetCore.Tests.OAuth;

public class AuthTests : OAuthTestBase
{
    private const string ClientMetadataDocumentUrl = $"{OAuthServerUrl}/client-metadata/cimd-client.json";

    public AuthTests(ITestOutputHelper outputHelper)
         : base(outputHelper)
    {
    }

    [Fact]
    public async Task CanAuthenticate()
    {
        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Fact]
    public async Task CannotAuthenticate_WithoutOAuthConfiguration()
    {
        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
        }, HttpClient, LoggerFactory);

        var httpEx = await Assert.ThrowsAsync<HttpRequestException>(async () => await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken));

        Assert.Equal(HttpStatusCode.Unauthorized, httpEx.StatusCode);
    }

    [Fact]
    public async Task CannotAuthenticate_WithUnregisteredClient()
    {
        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "unregistered-demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        // The EqualException is thrown by HandleAuthorizationUrlAsync when the /authorize request gets a 400
        var equalEx = await Assert.ThrowsAsync<EqualException>(async () => await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken));
    }

    [Fact]
    public async Task CanAuthenticate_WithDynamicClientRegistration()
    {
        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new ClientOAuthOptions()
            {
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
                DynamicClientRegistration = new()
                {
                    ClientName = "Test MCP Client",
                    ClientUri = new Uri("https://example.com"),
                },
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Fact]
    public async Task CanAuthenticate_WithClientMetadataDocument()
    {
        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new ClientOAuthOptions()
            {
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
                ClientMetadataDocumentUri = new Uri(ClientMetadataDocumentUrl)
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Fact]
    public async Task UsesDynamicClientRegistration_WhenCimdNotSupported()
    {
        // Disable CIMD support on the test OAuth server so the client
        // falls back to dynamic registration even if a CIMD URL is provided.
        TestOAuthServer.ClientIdMetadataDocumentSupported = false;

        await using var app = await StartMcpServerAsync();

        // Provide an invalid CIMD URL; if CIMD were used, auth would fail.
        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new ClientOAuthOptions()
            {
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
                ClientMetadataDocumentUri = new Uri("http://invalid-cimd.example.com"),
                DynamicClientRegistration = new()
                {
                    ClientName = "Test MCP Client (No CIMD)",
                    ClientUri = new Uri("https://example.com/no-cimd"),
                },
            },
        }, HttpClient, LoggerFactory);

        // Should succeed via dynamic client registration.
        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Fact]
    public async Task DoesNotUseClientMetadataDocument_WhenClientIdIsSpecified()
    {
        await using var app = await StartMcpServerAsync();

        // Provide an invalid CIMD URL; if CIMD were used, auth would fail.
        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new ClientOAuthOptions()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
                ClientMetadataDocumentUri = new Uri("http://invalid-cimd.example.com"),
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Theory]
    [InlineData("http://localhost:7029/client-metadata/cimd-client.json")] // Non-HTTPS Scheme
    [InlineData("http://localhost:7029")] // Missing path
    public async Task CannotAuthenticate_WithInvalidClientMetadataDocument(string uri)
    {
        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new ClientOAuthOptions()
            {
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
                ClientMetadataDocumentUri = new Uri(uri),
            },
        }, HttpClient, LoggerFactory);

        var ex = await Assert.ThrowsAsync<McpException>(() => McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken));

        Assert.StartsWith("Failed to handle unauthorized response", ex.Message);
    }

    [Fact]
    public async Task CanAuthenticate_WithTokenRefresh()
    {
        var hasForcedRefresh = false;

        Builder.Services.AddMcpServer(options =>
        {
            options.ToolCollection = new();
        });

        await using var app = await StartMcpServerAsync(configureMiddleware: app =>
        {
            // Add middleware to intercept list tools requests and force a token refresh on the first call
            app.Use(async (context, next) =>
            {
                if (context.Request.Method == HttpMethods.Post && context.Request.Path == "/" && !hasForcedRefresh)
                {
                    // Enable buffering so we can read the request body multiple times
                    context.Request.EnableBuffering();

                    // Read the request body to check if it's calling tools/list
                    var message = await JsonSerializer.DeserializeAsync(
                        context.Request.Body,
                        McpJsonUtilities.DefaultOptions.GetTypeInfo(typeof(JsonRpcMessage)),
                        context.RequestAborted) as JsonRpcMessage;

                    // Reset the request body position so MapMcp can read it
                    context.Request.Body.Position = 0;

                    // Check if this is a tools/list request
                    if (message is JsonRpcRequest request && request.Method == "tools/list")
                    {
                        hasForcedRefresh = true;

                        // Return 401 to force token refresh
                        await context.ChallengeAsync(JwtBearerDefaults.AuthenticationScheme);
                        await context.Response.StartAsync(context.RequestAborted);
                        await context.Response.Body.FlushAsync(context.RequestAborted);
                        return; // Short-circuit, don't call next()
                    }
                }

                await next(context);
            });
        });

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        await client.ListToolsAsync(cancellationToken: TestContext.Current.CancellationToken);

        Assert.True(TestOAuthServer.HasRefreshedToken);
    }

    [Fact]
    public async Task CanAuthenticate_WithExtraParams()
    {
        await using var app = await StartMcpServerAsync();

        Uri? lastAuthorizationUri = null;

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = (uri, redirect, ct) =>
                {
                    lastAuthorizationUri = uri;
                    return HandleAuthorizationUrlAsync(uri, redirect, ct);
                },
                AdditionalAuthorizationParameters = new Dictionary<string, string>
                {
                    ["custom_param"] = "custom_value",
                }
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        Assert.NotNull(lastAuthorizationUri?.Query);
        Assert.Contains("custom_param=custom_value", lastAuthorizationUri?.Query);
    }

    [Fact]
    public async Task CannotOverrideExistingParameters_WithExtraParams()
    {
        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
                AdditionalAuthorizationParameters = new Dictionary<string, string>
                {
                    ["redirect_uri"] = "custom_value",
                }
            },
        }, HttpClient, LoggerFactory);

        await Assert.ThrowsAsync<ArgumentException>(() => McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken));
    }

    [Fact]
    public async Task CanAuthenticate_WithoutResourceInWwwAuthenticateHeader()
    {
        await using var app = await StartMcpServerAsync(authScheme: JwtBearerDefaults.AuthenticationScheme);

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Fact]
    public async Task CanAuthenticate_WithoutResourceInWwwAuthenticateHeader_WithPathSuffix()
    {
        const string serverPath = "/mcp";
        await using var app = await StartMcpServerAsync(serverPath, authScheme: JwtBearerDefaults.AuthenticationScheme);

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new Uri($"{McpServerUrl}{serverPath}"),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Fact]
    public async Task AuthorizationFlow_UsesScopeFromProtectedResourceMetadata()
    {
        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.ResourceMetadata!.ScopesSupported = ["mcp:tools", "files:read"];
        });

        await using var app = await StartMcpServerAsync();

        string? requestedScope = null;

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = (uri, redirect, ct) =>
                {
                    var query = QueryHelpers.ParseQuery(uri.Query);
                    requestedScope = query["scope"].ToString();
                    return HandleAuthorizationUrlAsync(uri, redirect, ct);
                },
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        Assert.Equal("mcp:tools files:read", requestedScope);
    }

    [Fact]
    public async Task AuthorizationFlow_UsesScopeFromChallengeHeader()
    {
        var challengeScopes = "challenge:read challenge:write";

        await using var app = Builder.Build();
        app.Use(next =>
        {
            return async context =>
            {
                await next(context);

                if (context.Response.StatusCode != 401)
                {
                    return;
                }

                context.Response.Headers.WWWAuthenticate = $"Bearer resource_metadata=\"{McpServerUrl}/.well-known/oauth-protected-resource\", scope=\"{challengeScopes}\"";
            };
        });
        app.UseAuthentication();
        app.UseAuthorization();

        app.MapMcp().RequireAuthorization();
        await app.StartAsync(TestContext.Current.CancellationToken);

        string? requestedScope = null;

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = (uri, redirect, ct) =>
                {
                    var query = QueryHelpers.ParseQuery(uri.Query);
                    requestedScope = query["scope"].ToString();
                    return HandleAuthorizationUrlAsync(uri, redirect, ct);
                },
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        Assert.Equal(challengeScopes, requestedScope);
    }

    [Fact]
    public async Task AuthorizationFlow_UsesScopeFromForbiddenHeader()
    {
        var adminScopes = "admin:read admin:write";

        Builder.Services.AddMcpServer()
            .WithTools([
                McpServerTool.Create([McpServerTool(Name = "admin-tool")]
                (ClaimsPrincipal user) =>
                {
                    // Tool now just checks if user has the required scopes
                    // If they don't, it shouldn't get here due to middleware
                    Assert.True(user.HasClaim("scope", adminScopes), "User should have admin scopes when tool executes");
                    return "Admin tool executed.";
                }),
            ]);

        string? requestedScope = null;

        await using var app = await StartMcpServerAsync(configureMiddleware: app =>
        {
            // Add middleware to intercept requests and check for admin-tool calls
            app.Use(async (context, next) =>
            {
                if (context.Request.Method == HttpMethods.Post && context.Request.Path == "/")
                {
                    // Enable buffering so we can read the request body multiple times
                    context.Request.EnableBuffering();

                    // Read the request body to check if it's calling admin-tool
                    var message = await JsonSerializer.DeserializeAsync(
                        context.Request.Body,
                        McpJsonUtilities.DefaultOptions.GetTypeInfo(typeof(JsonRpcMessage)),
                        context.RequestAborted) as JsonRpcMessage;

                    // Reset the request body position so MapMcp can read it
                    context.Request.Body.Position = 0;

                    // Check if this is a tools/call request for admin-tool
                    if (message is JsonRpcRequest request && request.Method == "tools/call")
                    {
                        var toolCallParams = JsonSerializer.Deserialize(
                            request.Params,
                            McpJsonUtilities.DefaultOptions.GetTypeInfo(typeof(CallToolRequestParams))) as CallToolRequestParams;

                        if (toolCallParams?.Name == "admin-tool")
                        {
                            // Check if user has required scopes
                            var user = context.User;
                            if (!user.HasClaim("scope", adminScopes))
                            {
                                // User lacks required scopes, return 403 before MapMcp processes the request
                                context.Response.StatusCode = StatusCodes.Status403Forbidden;
                                context.Response.Headers.WWWAuthenticate = $"Bearer error=\"insufficient_scope\", resource_metadata=\"{McpServerUrl}/.well-known/oauth-protected-resource\", scope=\"{adminScopes}\"";
                                await context.Response.StartAsync(context.RequestAborted);
                                await context.Response.Body.FlushAsync(context.RequestAborted);
                                return; // Short-circuit, don't call next()
                            }
                        }
                    }
                }

                await next(context);
            });
        });

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = (uri, redirect, ct) =>
                {
                    var query = QueryHelpers.ParseQuery(uri.Query);
                    requestedScope = query["scope"].ToString();
                    return HandleAuthorizationUrlAsync(uri, redirect, ct);
                },
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        Assert.Equal("mcp:tools", requestedScope);

        var adminResult = await client.CallToolAsync("admin-tool", cancellationToken: TestContext.Current.CancellationToken);
        Assert.Equal("Admin tool executed.", adminResult.Content[0].ToString());

        Assert.Equal(adminScopes, requestedScope);
    }

    [Fact]
    public async Task AuthorizationFails_WhenResourceMetadataPortDiffers()
    {
        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.ResourceMetadata!.Resource = "http://localhost:5999";
        });

        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await Assert.ThrowsAsync<McpException>(() => McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken));
    }

    [Fact]
    public async Task CannotAuthenticate_WhenProtectedResourceMetadataMissingResource()
    {
        TestOAuthServer.RequireResource = false;

        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.Events.OnResourceMetadataRequest = async context =>
            {
                context.HandleResponse();

                var metadata = new ProtectedResourceMetadata
                {
                    AuthorizationServers = { OAuthServerUrl },
                    ScopesSupported = ["mcp:tools"],
                };

                await Results.Json(metadata, McpJsonUtilities.DefaultOptions).ExecuteAsync(context.HttpContext);
            };
        });

        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        var ex = await Assert.ThrowsAsync<McpException>(() => McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken));

        Assert.Contains("Resource URI in metadata", ex.Message);
    }

    [Fact]
    public async Task CanAuthenticate_WithAuthorizationServerPathInsertionMetadata()
    {
        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.ResourceMetadata!.AuthorizationServers = [$"{OAuthServerUrl}/tenant1"];
        });

        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        var requests = TestOAuthServer.MetadataRequests.ToArray();
        Assert.Contains("/.well-known/oauth-authorization-server/tenant1", requests);
    }

    [Fact]
    public async Task CanAuthenticate_WithAuthorizationServerPathFallbacks()
    {
        const string issuerPath = "/subdir/tenant2";
        TestOAuthServer.DisabledMetadataPaths.Add($"/.well-known/oauth-authorization-server{issuerPath}");
        TestOAuthServer.DisabledMetadataPaths.Add($"/.well-known/openid-configuration{issuerPath}");

        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.ResourceMetadata!.AuthorizationServers = [$"{OAuthServerUrl}{issuerPath}"];
        });

        await using var app = await StartMcpServerAsync();

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        Assert.Equal(
            [
                $"/.well-known/oauth-authorization-server{issuerPath}",
                $"/.well-known/openid-configuration{issuerPath}",
                $"{issuerPath}/.well-known/openid-configuration",
                "/.well-known/openid-configuration",
            ],
            TestOAuthServer.MetadataRequests);
    }

    [Fact]
    public async Task CanAuthenticate_WithResourceMetadataPathFallbacks()
    {
        const string resourcePath = "/mcp";
        List<string> wellKnownRequests = [];

        Builder.Services.Configure<AuthenticationOptions>(options => options.DefaultChallengeScheme = JwtBearerDefaults.AuthenticationScheme);
        await using var app = Builder.Build();

        var metadata = new ProtectedResourceMetadata
        {
            Resource = $"{McpServerUrl}{resourcePath}",
            AuthorizationServers = { OAuthServerUrl },
        };

        app.Use(async (context, next) =>
        {
            if (context.Request.Path.StartsWithSegments("/.well-known/oauth-protected-resource", out var remaining))
            {
                wellKnownRequests.Add(context.Request.Path);
                if (remaining.HasValue)
                {
                    context.Response.StatusCode = StatusCodes.Status404NotFound;
                    return;
                }
            }

            await next();
        });

        app.UseAuthentication();
        app.UseAuthorization();

        app.MapMcp(resourcePath).RequireAuthorization();

        await app.StartAsync(TestContext.Current.CancellationToken);

        var endpoint = new Uri(new Uri(McpServerUrl), resourcePath);

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = endpoint,
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);

        Assert.Equal(
            [
                $"/.well-known/oauth-protected-resource{resourcePath}",
                "/.well-known/oauth-protected-resource"
            ],
            wellKnownRequests);
    }

    [Fact]
    public async Task CannotAuthenticate_WhenResourceMetadataResourceIsNonRootParentPath()
    {
        const string configuredResourcePath = "/mcp";
        const string requestedResourcePath = "/mcp/tools";

        // Remove resource_metadata from the WWW-Authenticate header, because we should only fall back at all (even to root) when it's missing.
        //
        // If the protected resource metadata was retrieved from a URL returned by the protected resource via the WWW-Authenticate resource_metadata parameter,
        // then the resource value returned MUST be identical to the URL that the client used to make the request to the resource server.
        // If these values are not identical, the data contained in the response MUST NOT be used.
        //
        // https://datatracker.ietf.org/doc/html/rfc9728/#section-3.3
        //
        // CannotAuthenticate_WhenWwwAuthenticateResourceMetadataIsRootPath validates we won't fall back to root in this case.
        // CanAuthenticate_WithResourceMetadataPathFallbacks validates we will fall back to root when resource_metadata is missing.
        Builder.Services.Configure<AuthenticationOptions>(options => options.DefaultChallengeScheme = JwtBearerDefaults.AuthenticationScheme);
        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.ResourceMetadata = new ProtectedResourceMetadata
            {
                Resource = $"{McpServerUrl}{configuredResourcePath}",
                AuthorizationServers = { OAuthServerUrl },
            };
        });

        await using var app = Builder.Build();

        app.MapMcp(requestedResourcePath).RequireAuthorization();

        await app.StartAsync(TestContext.Current.CancellationToken);

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new Uri($"{McpServerUrl}{requestedResourcePath}"),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        var ex = await Assert.ThrowsAsync<McpException>(async () =>
        {
            await McpClient.CreateAsync(
                transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
        });

        Assert.Contains("does not match", ex.Message);
    }

    [Fact]
    public async Task CannotAuthenticate_WhenWwwAuthenticateResourceMetadataIsRootPath()
    {
        const string requestedResourcePath = "/mcp/tools";

        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.ResourceMetadata = new ProtectedResourceMetadata
            {
                Resource = McpServerUrl,
                AuthorizationServers = { OAuthServerUrl },
            };
        });

        await using var app = Builder.Build();

        app.MapMcp(requestedResourcePath).RequireAuthorization();

        await app.StartAsync(TestContext.Current.CancellationToken);

        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new Uri($"{McpServerUrl}{requestedResourcePath}"),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        var ex = await Assert.ThrowsAsync<McpException>(async () =>
        {
            await McpClient.CreateAsync(
                transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
        });

        Assert.Contains("does not match", ex.Message);
    }

    [Fact]
    public async Task ResourceMetadata_DoesNotAddTrailingSlash()
    {
        // This test verifies that automatically derived resource URIs don't have trailing slashes
        // and that the client doesn't add them during authentication
        
        // Don't explicitly set Resource - let it be derived from the request
        await using var app = await StartMcpServerAsync();

        // First, manually check the PRM document doesn't contain a trailing slash
        using var metadataResponse = await HttpClient.GetAsync(
            "/.well-known/oauth-protected-resource",
            TestContext.Current.CancellationToken
        );

        Assert.Equal(HttpStatusCode.OK, metadataResponse.StatusCode);

        var metadata = await metadataResponse.Content.ReadFromJsonAsync<ProtectedResourceMetadata>(
            McpJsonUtilities.DefaultOptions,
            TestContext.Current.CancellationToken
        );

        Assert.NotNull(metadata);
        Assert.Equal("http://localhost:5000", metadata.Resource);
        Assert.DoesNotMatch(@"/$", metadata.Resource); // No trailing slash

        // Then authenticate with the client - this will use the derived resource URI
        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        // This should succeed - the client should not add a trailing slash
        // If the client incorrectly added a trailing slash, ValidResources would reject it
        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }

    [Fact]
    public async Task ResourceMetadata_PreservesExplicitTrailingSlash()
    {
        // This test verifies that explicitly configured trailing slashes are preserved
        const string resourceWithTrailingSlash = "http://localhost:5000/";
        
        // Configure ValidResources to accept the trailing slash version for this test
        TestOAuthServer.ValidResources = [resourceWithTrailingSlash, "http://localhost:5000/mcp"];
        
        Builder.Services.Configure<McpAuthenticationOptions>(McpAuthenticationDefaults.AuthenticationScheme, options =>
        {
            options.ResourceMetadata = new ProtectedResourceMetadata
            {
                Resource = resourceWithTrailingSlash,
                AuthorizationServers = { OAuthServerUrl },
                ScopesSupported = ["mcp:tools"],
            };
        });

        await using var app = await StartMcpServerAsync();

        // First, manually check the PRM document contains the trailing slash
        using var metadataResponse = await HttpClient.GetAsync(
            "/.well-known/oauth-protected-resource",
            TestContext.Current.CancellationToken
        );

        Assert.Equal(HttpStatusCode.OK, metadataResponse.StatusCode);

        var metadata = await metadataResponse.Content.ReadFromJsonAsync<ProtectedResourceMetadata>(
            McpJsonUtilities.DefaultOptions,
            TestContext.Current.CancellationToken
        );

        Assert.NotNull(metadata);
        Assert.Equal(resourceWithTrailingSlash, metadata.Resource);
        Assert.Matches(@"/$", metadata.Resource); // Has trailing slash

        // Then authenticate with the client
        await using var transport = new HttpClientTransport(new()
        {
            Endpoint = new(McpServerUrl),
            OAuth = new()
            {
                ClientId = "demo-client",
                ClientSecret = "demo-secret",
                RedirectUri = new Uri("http://localhost:1179/callback"),
                AuthorizationRedirectDelegate = HandleAuthorizationUrlAsync,
            },
        }, HttpClient, LoggerFactory);

        // This should succeed with the explicitly configured trailing slash
        // If the client incorrectly trimmed the slash, ValidResources would reject it
        await using var client = await McpClient.CreateAsync(
            transport, loggerFactory: LoggerFactory, cancellationToken: TestContext.Current.CancellationToken);
    }
}