feat(auth): Microsoft OAuth sign-in/link + self-serve signup via Google/Microsoft

Wave 7. Mirrors the existing Google ID-token-exchange pattern (Program.cs
smart-scheme dispatch, JWT bearer scheme, AuthController exchange/link/
unlink endpoints, ApplicationUser fields, reconciler columns) for
Microsoft Entra ID + personal accounts via the multi-tenant "common"
endpoint.

Google/Microsoft sign-in previously only worked for accounts already
linked to an existing local user -- there was no way to actually sign
up via OAuth. Both exchange endpoints now create a new user when no
match is found and Auth:AllowRegistration is true, same gate as
email/password registration.

Frontend: new MicrosoftAuthCard (MSAL popup flow -- Microsoft has no
vanilla-JS equivalent to Google's Identity Services script) wired into
the login page's provider tabs and the profile page's account-linking
section. REACT_APP_MICROSOFT_CLIENT_ID env var, Auth:MicrosoftClientId
config gate on the backend.

JobTrackerApi.Tests/AttachmentFlagsRecomputeTests.cs

@@ -0,0 +1,111 @@
+using JobTrackerApi.Controllers;
+using JobTrackerApi.Data;
+using JobTrackerApi.Models;
+using JobTrackerApi.Services;
+using JobTrackerApi.Tests.TestSupport;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.Extensions.Configuration;
+using Microsoft.Extensions.Hosting;
+using Microsoft.AspNetCore.Http;
+using Microsoft.AspNetCore.Mvc;
+using Moq;
+using Xunit;
+
+namespace JobTrackerApi.Tests;
+
+// JobApplication.HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived from
+// Attachment rows (backlog Wave 3), not manually settable. These tests exercise the single
+// place they're written: AttachmentsController's Purpose-change and Delete paths.
+public sealed class AttachmentFlagsRecomputeTests
+{
+    [Fact]
+    public async Task Changing_purpose_to_resume_sets_HasResume()
+    {
+        await using var db = TestHostFactory.CreateInMemoryDb();
+        var (job, attachment) = await SeedJobWithAttachmentAsync(db, purpose: "other");
+        var controller = CreateController(db);
+
+        var result = await controller.Rename(attachment.Id, new AttachmentsController.UpdateAttachmentRequest(null, "resume", null), CancellationToken.None);
+
+        Assert.IsType<NoContentResult>(result);
+        var updated = await db.JobApplications.SingleAsync(j => j.Id == job.Id);
+        Assert.True(updated.HasResume);
+        Assert.True(updated.HasOtherAttachment == false);
+    }
+
+    [Fact]
+    public async Task Deleting_the_only_resume_attachment_clears_HasResume()
+    {
+        await using var db = TestHostFactory.CreateInMemoryDb();
+        var (job, attachment) = await SeedJobWithAttachmentAsync(db, purpose: "resume");
+        var controller = CreateController(db);
+
+        var result = await controller.Delete(attachment.Id, CancellationToken.None);
+
+        Assert.IsType<NoContentResult>(result);
+        var updated = await db.JobApplications.SingleAsync(j => j.Id == job.Id);
+        Assert.False(updated.HasResume);
+    }
+
+    [Fact]
+    public async Task Attachment_with_case_study_purpose_counts_as_other()
+    {
+        await using var db = TestHostFactory.CreateInMemoryDb();
+        var (job, attachment) = await SeedJobWithAttachmentAsync(db, purpose: "resume");
+        var controller = CreateController(db);
+
+        await controller.Rename(attachment.Id, new AttachmentsController.UpdateAttachmentRequest(null, "case-study", null), CancellationToken.None);
+
+        var updated = await db.JobApplications.SingleAsync(j => j.Id == job.Id);
+        Assert.False(updated.HasResume);
+        Assert.True(updated.HasOtherAttachment);
+    }
+
+    private static async Task<(JobApplication Job, Attachment Attachment)> SeedJobWithAttachmentAsync(JobTrackerContext db, string purpose)
+    {
+        var company = new Company { Name = "Acme", OwnerUserId = "user-1" };
+        db.Companies.Add(company);
+        await db.SaveChangesAsync();
+
+        var job = new JobApplication { JobTitle = "Backend Developer", CompanyId = company.Id, OwnerUserId = "user-1" };
+        db.JobApplications.Add(job);
+        await db.SaveChangesAsync();
+
+        var attachment = new Attachment
+        {
+            JobApplicationId = job.Id,
+            FileName = "file.pdf",
+            FilePath = Path.Combine(Path.GetTempPath(), $"jobtracker-attachment-test-{Guid.NewGuid():N}.pdf"),
+            FileType = "application/pdf",
+            FileSize = 100,
+            Purpose = purpose,
+        };
+        db.Attachments.Add(attachment);
+        await db.SaveChangesAsync();
+
+        job.HasResume = purpose == "resume";
+        job.HasOtherAttachment = purpose is not ("resume" or "cover-letter" or "portfolio");
+        await db.SaveChangesAsync();
+
+        return (job, attachment);
+    }
+
+    private static AttachmentsController CreateController(JobTrackerContext db)
+    {
+        var tempRoot = Path.Combine(Path.GetTempPath(), $"jobtracker-attachments-tests-{Guid.NewGuid():N}");
+        Directory.CreateDirectory(tempRoot);
+
+        var config = new ConfigurationBuilder()
+            .AddInMemoryCollection(new Dictionary<string, string?> { ["Data:Root"] = tempRoot })
+            .Build();
+
+        var env = new Mock<IHostEnvironment>();
+        env.SetupGet(x => x.ContentRootPath).Returns(tempRoot);
+        var paths = new AppPaths(config, env.Object);
+
+        return new AttachmentsController(paths, db)
+        {
+            ControllerContext = new ControllerContext { HttpContext = new DefaultHttpContext() }
+        };
+    }
+}

JobTrackerApi.Tests/AuthAndSystemControllerTests.cs

@@ -25,7 +25,7 @@ public sealed class AuthAndSystemControllerTests
         userManager.Setup(x => x.GetUserAsync(It.IsAny<System.Security.Claims.ClaimsPrincipal>())).ReturnsAsync(user);
         userManager.Setup(x => x.UpdateAsync(user)).ReturnsAsync(IdentityResult.Success);
 
-        var controller = new AuthController(BuildConfig(), userManager.Object, Mock.Of<ITokenService>(), Mock.Of<IAppEmailSender>(), Mock.Of<IGoogleTokenValidator>(), NullLogger<AuthController>.Instance);
+        var controller = new AuthController(BuildConfig(), userManager.Object, Mock.Of<ITokenService>(), Mock.Of<IAppEmailSender>(), Mock.Of<IGoogleTokenValidator>(), Mock.Of<IMicrosoftTokenValidator>(), NullLogger<AuthController>.Instance);
 
         var result = await controller.UpdateProfile(new AuthController.UpdateProfileRequest(" new@example.com ", " newuser ", " Ada ", " Lovelace ", " Ada L. ", null, null));
 
@@ -50,7 +50,7 @@ public sealed class AuthAndSystemControllerTests
             .Setup(x => x.SendAsync(user.Email!, It.IsAny<string>(), It.IsAny<string>(), It.IsAny<CancellationToken>()))
             .ThrowsAsync(new InvalidOperationException("SMTP unavailable"));
 
-        var controller = new AuthController(BuildConfig(), userManager.Object, Mock.Of<ITokenService>(), emailSender.Object, Mock.Of<IGoogleTokenValidator>(), NullLogger<AuthController>.Instance)
+        var controller = new AuthController(BuildConfig(), userManager.Object, Mock.Of<ITokenService>(), emailSender.Object, Mock.Of<IGoogleTokenValidator>(), Mock.Of<IMicrosoftTokenValidator>(), NullLogger<AuthController>.Instance)
         {
             ControllerContext = new ControllerContext
             {
@@ -91,7 +91,7 @@ public sealed class AuthAndSystemControllerTests
             .Setup(x => x.ValidateAsync("google-token", It.IsAny<CancellationToken>()))
             .ReturnsAsync(new GoogleTokenPrincipal("google-subject", "dj@cesnimda.co.uk", true, "Dan", "Jones", "Dan Jones"));
 
-        var controller = new AuthController(BuildConfig(), userManager.Object, tokenService.Object, Mock.Of<IAppEmailSender>(), googleValidator.Object, NullLogger<AuthController>.Instance)
+        var controller = new AuthController(BuildConfig(), userManager.Object, tokenService.Object, Mock.Of<IAppEmailSender>(), googleValidator.Object, Mock.Of<IMicrosoftTokenValidator>(), NullLogger<AuthController>.Instance)
         {
             ControllerContext = new ControllerContext
             {
@@ -110,6 +110,76 @@ public sealed class AuthAndSystemControllerTests
         Assert.NotNull(user.GoogleLinkedAt);
     }
 
+    [Fact]
+    public async Task Exchange_microsoft_token_creates_new_user_when_registration_allowed()
+    {
+        var userManager = CreateUserManager();
+        userManager.Setup(x => x.Users).Returns(new TestAsyncEnumerable<ApplicationUser>(new List<ApplicationUser>()));
+        userManager.Setup(x => x.FindByEmailAsync("new.hire@example.com")).ReturnsAsync((ApplicationUser?)null);
+        ApplicationUser? created = null;
+        userManager
+            .Setup(x => x.CreateAsync(It.IsAny<ApplicationUser>()))
+            .Callback<ApplicationUser>(u => created = u)
+            .ReturnsAsync(IdentityResult.Success);
+        userManager.Setup(x => x.UpdateAsync(It.IsAny<ApplicationUser>())).ReturnsAsync(IdentityResult.Success);
+
+        var tokenService = new Mock<ITokenService>();
+        tokenService.Setup(x => x.CreateAccessTokenAsync(It.IsAny<ApplicationUser>(), It.IsAny<CancellationToken>())).ReturnsAsync("app-token");
+
+        var microsoftValidator = new Mock<IMicrosoftTokenValidator>();
+        microsoftValidator
+            .Setup(x => x.ValidateAsync("microsoft-token", It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new MicrosoftTokenPrincipal("ms-subject", "new.hire@example.com", true, "New", "Hire", "New Hire"));
+
+        var config = new ConfigurationBuilder()
+            .AddInMemoryCollection(new Dictionary<string, string?> { ["Auth:AllowRegistration"] = "true" })
+            .Build();
+
+        var controller = new AuthController(config, userManager.Object, tokenService.Object, Mock.Of<IAppEmailSender>(), Mock.Of<IGoogleTokenValidator>(), microsoftValidator.Object, NullLogger<AuthController>.Instance)
+        {
+            ControllerContext = new ControllerContext
+            {
+                HttpContext = new DefaultHttpContext()
+            }
+        };
+
+        var result = await controller.ExchangeMicrosoftToken(new AuthController.MicrosoftTokenRequest("microsoft-token"), CancellationToken.None);
+
+        var ok = Assert.IsType<OkObjectResult>(result.Result);
+        var payload = Assert.IsType<AuthController.AuthSessionResult>(ok.Value);
+        Assert.True(payload.Authenticated);
+        Assert.Equal("microsoft", payload.Provider);
+        Assert.NotNull(created);
+        Assert.Equal("new.hire@example.com", created!.Email);
+        Assert.Equal("ms-subject", created.MicrosoftSubject);
+    }
+
+    [Fact]
+    public async Task Exchange_microsoft_token_rejects_unmatched_account_when_registration_disabled()
+    {
+        var userManager = CreateUserManager();
+        userManager.Setup(x => x.Users).Returns(new TestAsyncEnumerable<ApplicationUser>(new List<ApplicationUser>()));
+        userManager.Setup(x => x.FindByEmailAsync("nobody@example.com")).ReturnsAsync((ApplicationUser?)null);
+
+        var microsoftValidator = new Mock<IMicrosoftTokenValidator>();
+        microsoftValidator
+            .Setup(x => x.ValidateAsync("microsoft-token", It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new MicrosoftTokenPrincipal("ms-subject", "nobody@example.com", true, null, null, null));
+
+        var controller = new AuthController(BuildConfig(), userManager.Object, Mock.Of<ITokenService>(), Mock.Of<IAppEmailSender>(), Mock.Of<IGoogleTokenValidator>(), microsoftValidator.Object, NullLogger<AuthController>.Instance)
+        {
+            ControllerContext = new ControllerContext
+            {
+                HttpContext = new DefaultHttpContext()
+            }
+        };
+
+        var result = await controller.ExchangeMicrosoftToken(new AuthController.MicrosoftTokenRequest("microsoft-token"), CancellationToken.None);
+
+        Assert.IsType<UnauthorizedObjectResult>(result.Result);
+        userManager.Verify(x => x.CreateAsync(It.IsAny<ApplicationUser>()), Times.Never);
+    }
+
     [Fact]
     public void Me_result_includes_google_link_details_for_local_users()
     {

JobTrackerApi.Tests/ClientErrorsControllerTests.cs

@@ -51,7 +51,7 @@ public sealed class ClientErrorsControllerTests
         var userManager = TestHostFactory.CreateUserManager();
         userManager.Setup(x => x.GetUserAsync(It.IsAny<ClaimsPrincipal>())).ReturnsAsync(user);
 
-        var controller = new AuthController(BuildConfig(), userManager.Object, Mock.Of<ITokenService>(), Mock.Of<IAppEmailSender>(), Mock.Of<IGoogleTokenValidator>(), Mock.Of<ILogger<AuthController>>())
+        var controller = new AuthController(BuildConfig(), userManager.Object, Mock.Of<ITokenService>(), Mock.Of<IAppEmailSender>(), Mock.Of<IGoogleTokenValidator>(), Mock.Of<IMicrosoftTokenValidator>(), Mock.Of<ILogger<AuthController>>())
         {
             ControllerContext = new ControllerContext
             {

JobTrackerApi.Tests/JobApplicationsEndpointBehaviorTests.cs

@@ -202,11 +202,7 @@ public sealed class JobApplicationsEndpointBehaviorTests
             CoverLetterText: null,
             JobUrl: null,
             DateApplied: null,
-            FeedbackRequestedAt: null,
-            HasResume: null,
-            HasCoverLetter: null,
-            HasPortfolio: null,
-            HasOtherAttachment: null);
+            FeedbackRequestedAt: null);
 
         var result = await controller.Create(request, CancellationToken.None);
 
@@ -255,10 +251,6 @@ public sealed class JobApplicationsEndpointBehaviorTests
             SalaryPeriod: "fortnight",
             NextAction: null,
             FollowUpAt: null,
-            HasResume: null,
-            HasCoverLetter: null,
-            HasPortfolio: null,
-            HasOtherAttachment: null,
             Notes: null,
             Description: null,
             TranslatedDescription: null,

JobTrackerApi.Tests/MicrosoftTokenValidatorTests.cs

@@ -0,0 +1,77 @@
+using System.IdentityModel.Tokens.Jwt;
+using System.Security.Claims;
+using System.Text;
+using JobTrackerApi.Services;
+using Microsoft.Extensions.Configuration;
+using Microsoft.IdentityModel.Protocols;
+using Microsoft.IdentityModel.Protocols.OpenIdConnect;
+using Microsoft.IdentityModel.Tokens;
+using Moq;
+using Xunit;
+
+namespace JobTrackerApi.Tests;
+
+public sealed class MicrosoftTokenValidatorTests
+{
+    private static (IConfiguration Config, Mock<IConfigurationManager<OpenIdConnectConfiguration>> ConfigManager, SymmetricSecurityKey Key) BuildHarness()
+    {
+        var config = new ConfigurationBuilder()
+            .AddInMemoryCollection(new Dictionary<string, string?> { ["Auth:MicrosoftClientId"] = "client-123" })
+            .Build();
+
+        var signingKey = new SymmetricSecurityKey(Encoding.UTF8.GetBytes("super-secret-signing-key-super-secret"));
+        var oidc = new OpenIdConnectConfiguration();
+        oidc.SigningKeys.Add(signingKey);
+
+        var configManager = new Mock<IConfigurationManager<OpenIdConnectConfiguration>>();
+        configManager.Setup(x => x.GetConfigurationAsync(It.IsAny<CancellationToken>())).ReturnsAsync(oidc);
+
+        return (config, configManager, signingKey);
+    }
+
+    [Fact]
+    public async Task ValidateAsync_accepts_tenant_scoped_issuer_and_maps_oid_to_subject()
+    {
+        var (config, configManager, signingKey) = BuildHarness();
+
+        var token = new JwtSecurityTokenHandler().WriteToken(new JwtSecurityToken(
+            issuer: "https://login.microsoftonline.com/9f2c1e3a-tenant/v2.0",
+            audience: "client-123",
+            claims: new[]
+            {
+                new Claim("oid", "ms-subject-1"),
+                new Claim("email", "demo@example.com"),
+                new Claim("given_name", "Demo"),
+                new Claim("family_name", "User"),
+                new Claim("name", "Demo User"),
+            },
+            expires: DateTime.UtcNow.AddMinutes(10),
+            signingCredentials: new SigningCredentials(signingKey, SecurityAlgorithms.HmacSha256)));
+
+        var validator = new MicrosoftTokenValidator(config, configManager.Object);
+        var result = await validator.ValidateAsync(token);
+
+        Assert.Equal("ms-subject-1", result.Subject);
+        Assert.Equal("demo@example.com", result.Email);
+        Assert.True(result.EmailVerified);
+        Assert.Equal("Demo", result.GivenName);
+        Assert.Equal("User", result.FamilyName);
+    }
+
+    [Fact]
+    public async Task ValidateAsync_rejects_non_microsoft_issuer()
+    {
+        var (config, configManager, signingKey) = BuildHarness();
+
+        var token = new JwtSecurityTokenHandler().WriteToken(new JwtSecurityToken(
+            issuer: "https://evil.example.com/v2.0",
+            audience: "client-123",
+            claims: new[] { new Claim("oid", "ms-subject-1") },
+            expires: DateTime.UtcNow.AddMinutes(10),
+            signingCredentials: new SigningCredentials(signingKey, SecurityAlgorithms.HmacSha256)));
+
+        var validator = new MicrosoftTokenValidator(config, configManager.Object);
+
+        await Assert.ThrowsAsync<InvalidOperationException>(() => validator.ValidateAsync(token));
+    }
+}

JobTrackerApi/Controllers/AttachmentsController.cs

@@ -59,6 +59,26 @@ namespace JobTrackerApi.Controllers
             return "other";
         }
 
+        // JobApplication.HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived
+        // from actual Attachment rows, not manually settable -- this is the single place they're
+        // written, called after every attachment mutation (upload/delete/purpose change) so they
+        // can never drift from what's actually attached.
+        private async Task RecomputeAttachmentFlagsAsync(int jobId, CancellationToken cancellationToken)
+        {
+            var job = await _db.JobApplications.FirstOrDefaultAsync(j => j.Id == jobId, cancellationToken);
+            if (job is null) return;
+
+            var purposes = await _db.Attachments
+                .Where(a => a.JobApplicationId == jobId)
+                .Select(a => a.Purpose)
+                .ToListAsync(cancellationToken);
+
+            job.HasResume = purposes.Any(p => p == "resume");
+            job.HasCoverLetter = purposes.Any(p => p == "cover-letter");
+            job.HasPortfolio = purposes.Any(p => p == "portfolio");
+            job.HasOtherAttachment = purposes.Any(p => p is not ("resume" or "cover-letter" or "portfolio"));
+        }
+
         [HttpGet("{jobId:int}")]
         public async Task<ActionResult<List<AttachmentDto>>> ListForJob([FromRoute] int jobId, CancellationToken cancellationToken)
         {
@@ -102,15 +122,23 @@ namespace JobTrackerApi.Controllers
                 att.UseForAi = request.UseForAi.Value;
             }
 
-            if (!string.IsNullOrWhiteSpace(request.Purpose))
+            var purposeChanged = !string.IsNullOrWhiteSpace(request.Purpose);
+            if (purposeChanged)
             {
-                att.Purpose = request.Purpose.Trim().ToLowerInvariant();
+                att.Purpose = request.Purpose!.Trim().ToLowerInvariant();
             }
 
             var rawName = (request.FileName ?? string.Empty).Trim();
             if (rawName.Length == 0)
             {
                 await _db.SaveChangesAsync(cancellationToken);
+                if (purposeChanged)
+                {
+                    // Recompute needs the Purpose change committed first -- a fresh query
+                    // wouldn't see the pending change yet.
+                    await RecomputeAttachmentFlagsAsync(att.JobApplicationId, cancellationToken);
+                    await _db.SaveChangesAsync(cancellationToken);
+                }
                 return NoContent();
             }
 
@@ -130,6 +158,11 @@ namespace JobTrackerApi.Controllers
             att.FileName = name;
             att.FilePath = newPath;
             await _db.SaveChangesAsync(cancellationToken);
+            if (purposeChanged)
+            {
+                await RecomputeAttachmentFlagsAsync(att.JobApplicationId, cancellationToken);
+                await _db.SaveChangesAsync(cancellationToken);
+            }
 
             return NoContent();
         }
@@ -141,8 +174,11 @@ namespace JobTrackerApi.Controllers
             if (att is null) return NotFound();
 
             var path = att.FilePath;
+            var jobId = att.JobApplicationId;
             _db.Attachments.Remove(att);
             await _db.SaveChangesAsync(cancellationToken);
+            await RecomputeAttachmentFlagsAsync(jobId, cancellationToken);
+            await _db.SaveChangesAsync(cancellationToken);
 
             try
             {
@@ -200,6 +236,8 @@ namespace JobTrackerApi.Controllers
                 });
             }
 
+            await _db.SaveChangesAsync(cancellationToken);
+            await RecomputeAttachmentFlagsAsync(jobId, cancellationToken);
             await _db.SaveChangesAsync(cancellationToken);
             return Ok();
         }

JobTrackerApi/Controllers/AuthController.cs

@@ -19,15 +19,17 @@ public sealed class AuthController : ControllerBase
     private readonly ITokenService _tokens;
     private readonly IAppEmailSender _email;
     private readonly IGoogleTokenValidator _googleTokens;
+    private readonly IMicrosoftTokenValidator _microsoftTokens;
     private readonly ILogger<AuthController> _logger;
 
-    public AuthController(IConfiguration cfg, UserManager<ApplicationUser> users, ITokenService tokens, IAppEmailSender email, IGoogleTokenValidator googleTokens, ILogger<AuthController> logger)
+    public AuthController(IConfiguration cfg, UserManager<ApplicationUser> users, ITokenService tokens, IAppEmailSender email, IGoogleTokenValidator googleTokens, IMicrosoftTokenValidator microsoftTokens, ILogger<AuthController> logger)
     {
         _cfg = cfg;
         _users = users;
         _tokens = tokens;
         _email = email;
         _googleTokens = googleTokens;
+        _microsoftTokens = microsoftTokens;
         _logger = logger;
     }
 
@@ -37,12 +39,14 @@ public sealed class AuthController : ControllerBase
     {
         var requireAuth = _cfg.GetValue("Auth:Require", false);
         var googleEnabled = !string.IsNullOrWhiteSpace((_cfg["Auth:GoogleClientId"] ?? string.Empty).Trim());
+        var microsoftEnabled = !string.IsNullOrWhiteSpace((_cfg["Auth:MicrosoftClientId"] ?? string.Empty).Trim());
         var allowRegistration = _cfg.GetValue("Auth:AllowRegistration", false);
 
         return Ok(new
         {
             requireAuth,
             googleEnabled,
+            microsoftEnabled,
             localEnabled = true,
             allowRegistration,
         });
@@ -52,6 +56,7 @@ public sealed class AuthController : ControllerBase
     public sealed record RegisterRequest(string Email, string Password, bool RememberMe = true);
     public sealed record AuthSessionResult(bool Authenticated, string Provider);
     public sealed record GoogleLinkDto(bool Linked, string? Email, DateTimeOffset? LinkedAt);
+    public sealed record MicrosoftLinkDto(bool Linked, string? Email, DateTimeOffset? LinkedAt);
     public sealed record MeResult(
         string Provider,
         string? Id,
@@ -64,7 +69,8 @@ public sealed class AuthController : ControllerBase
         string? ProfileCvStructureJson,
         string? AvatarImageDataUrl,
         IList<string> Roles,
-        GoogleLinkDto? GoogleLink);
+        GoogleLinkDto? GoogleLink,
+        MicrosoftLinkDto? MicrosoftLink);
     private const int MaxAvatarBytes = 1_000_000;
     private static readonly HashSet<string> AllowedAvatarExtensions = new(StringComparer.OrdinalIgnoreCase)
     {
@@ -72,6 +78,7 @@ public sealed class AuthController : ControllerBase
     };
     public sealed record UpdateProfileRequest(string? Email, string? UserName, string? FirstName, string? LastName, string? DisplayName, string? ProfileCvText, string? ProfileCvStructureJson);
     public sealed record GoogleTokenRequest(string Token, bool RememberMe = true);
+    public sealed record MicrosoftTokenRequest(string Token, bool RememberMe = true);
 
     [HttpPost("login")]
     [AllowAnonymous]
@@ -155,7 +162,24 @@ public sealed class AuthController : ControllerBase
 
         if (user is null)
         {
-            return Unauthorized("This Google account is not linked to a Jobbjakt user yet.");
+            if (!google.EmailVerified || string.IsNullOrWhiteSpace(google.Email))
+            {
+                return Unauthorized("This Google account is not linked to a Jobbjakt user yet.");
+            }
+
+            var allowRegistration = _cfg.GetValue("Auth:AllowRegistration", false);
+            if (!allowRegistration)
+            {
+                return Unauthorized("This Google account is not linked to a Jobbjakt user yet.");
+            }
+
+            user = new ApplicationUser { UserName = google.Email, Email = google.Email, EmailConfirmed = true };
+            var created = await _users.CreateAsync(user);
+            if (!created.Succeeded)
+            {
+                return BadRequest(string.Join("; ", created.Errors.Select(e => e.Description)));
+            }
+            _logger.LogInformation("Created new user via Google sign-up for {Email}", google.Email);
         }
 
         if (string.IsNullOrWhiteSpace(user.GoogleSubject) || !string.Equals(user.GoogleSubject, google.Subject, StringComparison.Ordinal))
@@ -173,6 +197,74 @@ public sealed class AuthController : ControllerBase
         return Ok(new AuthSessionResult(true, "google"));
     }
 
+    [HttpPost("microsoft/exchange")]
+    [AllowAnonymous]
+    [EnableRateLimiting("auth-login")]
+    public async Task<ActionResult<AuthSessionResult>> ExchangeMicrosoftToken([FromBody] MicrosoftTokenRequest request, CancellationToken cancellationToken)
+    {
+        var token = (request.Token ?? string.Empty).Trim();
+        if (token.Length == 0) return BadRequest("Microsoft token is required.");
+
+        MicrosoftTokenPrincipal microsoft;
+        try
+        {
+            microsoft = await _microsoftTokens.ValidateAsync(token, cancellationToken);
+        }
+        catch (Exception ex)
+        {
+            return Unauthorized(ex.Message);
+        }
+
+        var user = await _users.Users.FirstOrDefaultAsync(
+            x => x.MicrosoftSubject == microsoft.Subject || (!string.IsNullOrWhiteSpace(microsoft.Email) && x.MicrosoftEmail == microsoft.Email),
+            cancellationToken);
+
+        if (user is null && microsoft.EmailVerified && !string.IsNullOrWhiteSpace(microsoft.Email))
+        {
+            user = await _users.FindByEmailAsync(microsoft.Email);
+            if (user is not null)
+            {
+                _logger.LogInformation("Auto-linking Microsoft sign-in for existing local account {Email}", microsoft.Email);
+            }
+        }
+
+        if (user is null)
+        {
+            if (!microsoft.EmailVerified || string.IsNullOrWhiteSpace(microsoft.Email))
+            {
+                return Unauthorized("This Microsoft account is not linked to a Jobbjakt user yet.");
+            }
+
+            var allowRegistration = _cfg.GetValue("Auth:AllowRegistration", false);
+            if (!allowRegistration)
+            {
+                return Unauthorized("This Microsoft account is not linked to a Jobbjakt user yet.");
+            }
+
+            user = new ApplicationUser { UserName = microsoft.Email, Email = microsoft.Email, EmailConfirmed = true };
+            var created = await _users.CreateAsync(user);
+            if (!created.Succeeded)
+            {
+                return BadRequest(string.Join("; ", created.Errors.Select(e => e.Description)));
+            }
+            _logger.LogInformation("Created new user via Microsoft sign-up for {Email}", microsoft.Email);
+        }
+
+        if (string.IsNullOrWhiteSpace(user.MicrosoftSubject) || !string.Equals(user.MicrosoftSubject, microsoft.Subject, StringComparison.Ordinal))
+        {
+            user.MicrosoftSubject = microsoft.Subject;
+            user.MicrosoftEmail = microsoft.Email;
+            user.MicrosoftLinkedAt ??= DateTimeOffset.UtcNow;
+            user.DisplayName ??= TrimOrNull(microsoft.Name);
+            user.FirstName ??= TrimOrNull(microsoft.GivenName);
+            user.LastName ??= TrimOrNull(microsoft.FamilyName);
+            await _users.UpdateAsync(user);
+        }
+
+        await SignInWithAppSessionAsync(user, request.RememberMe, cancellationToken);
+        return Ok(new AuthSessionResult(true, "microsoft"));
+    }
+
     [HttpPost("logout")]
     public IActionResult Logout()
     {
@@ -202,7 +294,11 @@ public sealed class AuthController : ControllerBase
         var email = User.FindFirstValue(ClaimTypes.Email) ?? User.FindFirstValue("email");
         var sub = User.FindFirstValue(ClaimTypes.NameIdentifier) ?? User.FindFirstValue("sub");
         var iss = User.FindFirstValue("iss") ?? string.Empty;
-        var provider = iss.Contains("accounts.google.com", StringComparison.OrdinalIgnoreCase) ? "google" : "external";
+        var provider = iss.Contains("accounts.google.com", StringComparison.OrdinalIgnoreCase)
+            ? "google"
+            : iss.Contains("login.microsoftonline.com", StringComparison.OrdinalIgnoreCase)
+                ? "microsoft"
+                : "external";
 
         return Ok(new MeResult(
             Provider: provider,
@@ -216,7 +312,8 @@ public sealed class AuthController : ControllerBase
             ProfileCvStructureJson: null,
             AvatarImageDataUrl: null,
             Roles: Array.Empty<string>(),
-            GoogleLink: provider == "google" ? new GoogleLinkDto(false, email, null) : null));
+            GoogleLink: provider == "google" ? new GoogleLinkDto(false, email, null) : null,
+            MicrosoftLink: provider == "microsoft" ? new MicrosoftLinkDto(false, email, null) : null));
     }
 
     [HttpPut("profile")]
@@ -322,6 +419,76 @@ public sealed class AuthController : ControllerBase
         return NoContent();
     }
 
+    [HttpPost("microsoft/link")]
+    [Authorize(AuthenticationSchemes = "local")]
+    public async Task<ActionResult<MicrosoftLinkDto>> LinkMicrosoft([FromBody] MicrosoftTokenRequest request, CancellationToken cancellationToken)
+    {
+        var user = await _users.GetUserAsync(User);
+        if (user is null)
+        {
+            return Unauthorized();
+        }
+
+        var token = (request.Token ?? string.Empty).Trim();
+        if (token.Length == 0) return BadRequest("Microsoft token is required.");
+
+        MicrosoftTokenPrincipal microsoft;
+        try
+        {
+            microsoft = await _microsoftTokens.ValidateAsync(token, cancellationToken);
+        }
+        catch (Exception ex)
+        {
+            return BadRequest(ex.Message);
+        }
+
+        var conflict = await _users.Users
+            .Where(x => x.Id != user.Id)
+            .FirstOrDefaultAsync(x => x.MicrosoftSubject == microsoft.Subject || (!string.IsNullOrWhiteSpace(microsoft.Email) && x.MicrosoftEmail == microsoft.Email), cancellationToken);
+        if (conflict is not null)
+        {
+            return Conflict("That Microsoft account is already linked to another Jobbjakt user.");
+        }
+
+        user.MicrosoftSubject = microsoft.Subject;
+        user.MicrosoftEmail = microsoft.Email;
+        user.MicrosoftLinkedAt = DateTimeOffset.UtcNow;
+        user.DisplayName ??= TrimOrNull(microsoft.Name);
+        user.FirstName ??= TrimOrNull(microsoft.GivenName);
+        user.LastName ??= TrimOrNull(microsoft.FamilyName);
+
+        var result = await _users.UpdateAsync(user);
+        if (!result.Succeeded)
+        {
+            return BadRequest(string.Join("; ", result.Errors.Select(e => e.Description)));
+        }
+
+        return Ok(new MicrosoftLinkDto(true, user.MicrosoftEmail, user.MicrosoftLinkedAt));
+    }
+
+    [HttpDelete("microsoft/link")]
+    [Authorize(AuthenticationSchemes = "local")]
+    public async Task<IActionResult> UnlinkMicrosoft()
+    {
+        var user = await _users.GetUserAsync(User);
+        if (user is null)
+        {
+            return Unauthorized();
+        }
+
+        user.MicrosoftSubject = null;
+        user.MicrosoftEmail = null;
+        user.MicrosoftLinkedAt = null;
+
+        var result = await _users.UpdateAsync(user);
+        if (!result.Succeeded)
+        {
+            return BadRequest(string.Join("; ", result.Errors.Select(e => e.Description)));
+        }
+
+        return NoContent();
+    }
+
     [HttpPost("avatar")]
     [Authorize(AuthenticationSchemes = "local")]
     [RequestSizeLimit(MaxAvatarBytes)]
@@ -571,6 +738,10 @@ public sealed class AuthController : ControllerBase
             GoogleLink: new GoogleLinkDto(
                 Linked: !string.IsNullOrWhiteSpace(user.GoogleSubject),
                 Email: user.GoogleEmail,
-                LinkedAt: user.GoogleLinkedAt));
+                LinkedAt: user.GoogleLinkedAt),
+            MicrosoftLink: new MicrosoftLinkDto(
+                Linked: !string.IsNullOrWhiteSpace(user.MicrosoftSubject),
+                Email: user.MicrosoftEmail,
+                LinkedAt: user.MicrosoftLinkedAt));
     }
 }

JobTrackerApi/Controllers/GmailController.cs

@@ -13,7 +13,7 @@ namespace JobTrackerApi.Controllers;
 [ApiController]
 [Route("api/gmail")]
 [Authorize]
-public sealed class GmailController : ControllerBase
+public sealed partial class GmailController : ControllerBase
 {
     private readonly IGmailOAuthService _gmail;
     private readonly IGmailJobMatchingService _matching;
@@ -37,77 +37,6 @@ public sealed class GmailController : ControllerBase
     private IEmailProvider Email => _providers.Get("gmail")
         ?? throw new InvalidOperationException("Gmail email provider is not registered.");
 
-    public sealed record GmailImportResultDto(int Imported, int Skipped, string? ThreadId);
-    public sealed record GmailImportMessageResultDto(int Imported, int Skipped, string MessageId, string? ThreadId, Correspondence? Message);
-    public sealed record ImportGmailMessageRequest(int JobApplicationId, string MessageId);
-    public sealed record ImportGmailThreadRequest(int JobApplicationId, string ThreadId, string[] MessageIds);
-    public sealed record RefreshLinkedThreadsRequest(int JobApplicationId);
-    public sealed record GmailThreadRefreshThreadDto(string ThreadId, int Imported, int Skipped, int TotalMessages, string Status, DateTimeOffset? LatestMessageDate);
-    public sealed record GmailThreadRefreshResultDto(int JobApplicationId, int ThreadsChecked, int Imported, int Skipped, bool HasLinkedThreads, DateTimeOffset RefreshedAt, IReadOnlyList<GmailThreadRefreshThreadDto> Threads);
-    public sealed record GmailJobMatchReasonDto(string Label, string Value, int Points);
-    public sealed record GmailJobMatchedMessageDto(
-        string Id,
-        string ThreadId,
-        string Subject,
-        string From,
-        string To,
-        DateTimeOffset? Date,
-        string Snippet,
-        int Score,
-        string Confidence,
-        bool AlreadyImported,
-        IReadOnlyList<string> MatchedQueries,
-        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons);
-    public sealed record GmailJobMatchedThreadDto(
-        string ThreadId,
-        string Subject,
-        int Score,
-        string Confidence,
-        bool HasImportedMessages,
-        int ImportedMessageCount,
-        int MessageCount,
-        DateTimeOffset? LatestDate,
-        IReadOnlyList<string> MatchedQueries,
-        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons,
-        IReadOnlyList<GmailJobMatchedMessageDto> Messages);
-    public sealed record GmailJobMatchesResponseDto(
-        int JobApplicationId,
-        string JobTitle,
-        string CompanyName,
-        string? RecruiterName,
-        string? RecruiterEmail,
-        IReadOnlyList<string> Queries,
-        int CandidateMessageCount,
-        int CandidateThreadCount,
-        IReadOnlyList<GmailJobMatchedThreadDto> Threads);
-
-    public sealed record GmailReviewJobCandidateDto(int JobApplicationId, string JobTitle, string CompanyName, int Score, string Confidence, IReadOnlyList<GmailJobMatchReasonDto> Reasons);
-    public sealed record GmailReviewThreadDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, int MessageCount, string Routing, bool HasImportedMessages, string? DecisionNote, IReadOnlyList<string> MatchedQueries, IReadOnlyList<GmailReviewJobCandidateDto> JobCandidates, IReadOnlyList<GmailJobMatchedMessageDto> Messages);
-    public sealed record GmailReviewQueueResponseDto(IReadOnlyList<string> Queries, int CandidateThreadCount, int AutoLinkThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, IReadOnlyList<GmailReviewThreadDto> Threads);
-    public sealed record SaveGmailReviewDecisionRequest(string ThreadId, string Decision, int? JobApplicationId, string? Note);
-    public sealed record GmailManualSyncRequest(int? LookbackDays, int? MaxResultsPerQuery, bool? AutoImportHighConfidence, bool? IncludeSpamTrash);
-    public sealed record GmailManualSyncResultDto(int QueriesRun, int CandidateThreadCount, int AutoLinkedThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, int ImportedMessages, int ImportedThreads, int SkippedMessages, int LookbackDays, bool IncludeSpamTrash, DateTimeOffset SyncedAt);
-    public sealed record GmailSuggestedJobCandidateDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, string? CompanyName, string? RecruiterName, string? RecruiterEmail, string? SuggestedJobTitle, string Routing, IReadOnlyList<string> MatchedQueries, string Preview);
-    public sealed record GmailSuggestedJobsResponseDto(int Count, IReadOnlyList<GmailSuggestedJobCandidateDto> Items);
-    public sealed record CreateSuggestedGmailJobRequest(string ThreadId, string CompanyName, string JobTitle, string? RecruiterName, string? RecruiterEmail, string? Notes, string? Status);
-    public sealed record CreatedSuggestedGmailJobDto(int JobApplicationId, int CompanyId, string ThreadId, int Imported, int Skipped);
-    public sealed record RelinkGmailThreadRequest(int JobApplicationId, string ThreadId, bool RemoveFromOtherJobs, string? Note);
-    public sealed record GmailRelinkResultDto(string ThreadId, int JobApplicationId, int Imported, int Skipped, int UnlinkedMessages);
-    public sealed record UnlinkGmailThreadRequest(int JobApplicationId, string ThreadId, string? Note, string? NextDecision);
-    public sealed record GmailUnlinkResultDto(string ThreadId, int JobApplicationId, int RemovedMessages, string Decision);
-
-    public sealed record GmailConnectionStatusDto(
-        bool Connected,
-        string? GmailAddress,
-        DateTimeOffset? ConnectedAt,
-        DateTimeOffset? LastSyncedAt,
-        DateTimeOffset? LastSyncAttemptedAt,
-        DateTimeOffset? LastSyncSucceededAt,
-        string? LastSyncMode,
-        string? LastSyncSource,
-        string? LastSyncStatus,
-        string? LastSyncError);
-
     [HttpGet("status")]
     public async Task<ActionResult<GmailConnectionStatusDto>> Status(CancellationToken cancellationToken)
     {
@@ -671,7 +600,9 @@ public sealed class GmailController : ControllerBase
             imported++;
         }
 
-        UpsertReviewDecision(await _db.GmailReviewDecisions.Where(x => x.OwnerUserId == ownerUserId).ToListAsync(cancellationToken), ownerUserId, request.ThreadId.Trim(), "linked", job.Id, request.Notes);
+        var suggestedJobReviewDecision = await _db.GmailReviewDecisions
+            .FirstOrDefaultAsync(x => x.OwnerUserId == ownerUserId && x.ThreadId == request.ThreadId.Trim(), cancellationToken);
+        UpsertReviewDecision(suggestedJobReviewDecision, ownerUserId, request.ThreadId.Trim(), "linked", job.Id, request.Notes);
         await _db.SaveChangesAsync(cancellationToken);
         return Ok(new CreatedSuggestedGmailJobDto(job.Id, company.Id, request.ThreadId.Trim(), imported, skipped));
     }
@@ -725,8 +656,9 @@ public sealed class GmailController : ControllerBase
             imported++;
         }
 
-        var reviewDecisions = await _db.GmailReviewDecisions.Where(x => x.OwnerUserId == ownerUserId).ToListAsync(cancellationToken);
-        UpsertReviewDecision(reviewDecisions, ownerUserId, threadId, "linked", job.Id, request.Note);
+        var reviewDecision = await _db.GmailReviewDecisions
+            .FirstOrDefaultAsync(x => x.OwnerUserId == ownerUserId && x.ThreadId == threadId, cancellationToken);
+        UpsertReviewDecision(reviewDecision, ownerUserId, threadId, "linked", job.Id, request.Note);
         await _db.SaveChangesAsync(cancellationToken);
         return Ok(new GmailRelinkResultDto(threadId, job.Id, imported, skipped, unlinkedMessages));
     }
@@ -752,10 +684,11 @@ public sealed class GmailController : ControllerBase
             _db.Correspondences.RemoveRange(messages);
         }
 
-        var reviewDecisions = await _db.GmailReviewDecisions.Where(x => x.OwnerUserId == ownerUserId).ToListAsync(cancellationToken);
+        var reviewDecision = await _db.GmailReviewDecisions
+            .FirstOrDefaultAsync(x => x.OwnerUserId == ownerUserId && x.ThreadId == threadId, cancellationToken);
         var nextDecision = (request.NextDecision ?? "review").Trim().ToLowerInvariant();
         if (nextDecision is not ("review" or "suggested" or "rejected")) nextDecision = "review";
-        UpsertReviewDecision(reviewDecisions, ownerUserId, threadId, nextDecision, null, request.Note);
+        UpsertReviewDecision(reviewDecision, ownerUserId, threadId, nextDecision, null, request.Note);
         await _db.SaveChangesAsync(cancellationToken);
         return Ok(new GmailUnlinkResultDto(threadId, job.Id, messages.Count, nextDecision));
     }
@@ -1012,40 +945,6 @@ public sealed class GmailController : ControllerBase
         return _matching.BuildJobQueries(job, queryOverride);
     }
 
-    private static string ApplySyncBoundary(string query, int lookbackDays, bool includeSpamTrash)
-    {
-        var bounded = (query ?? string.Empty).Trim();
-        if (!bounded.Contains("newer_than:", StringComparison.OrdinalIgnoreCase))
-        {
-            bounded = string.IsNullOrWhiteSpace(bounded)
-                ? $"newer_than:{lookbackDays}d"
-                : $"{bounded} newer_than:{lookbackDays}d";
-        }
-
-        if (!includeSpamTrash)
-        {
-            if (!bounded.Contains("in:spam", StringComparison.OrdinalIgnoreCase)) bounded += " -in:spam";
-            if (!bounded.Contains("in:trash", StringComparison.OrdinalIgnoreCase)) bounded += " -in:trash";
-        }
-
-        return bounded.Trim();
-    }
-
-    private static bool LooksLikeJobRelatedThread(IReadOnlyList<GmailQueryMatchedMessage> orderedMessages)
-    {
-        var sample = string.Join("\n", orderedMessages.Select(item => string.Join(" ", new[] { item.Message.Subject, item.Message.From, item.Message.Snippet }.Where(value => !string.IsNullOrWhiteSpace(value)))));
-        if (string.IsNullOrWhiteSpace(sample)) return false;
-        return sample.Contains("interview", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("application", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("recruit", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("role", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("position", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("offer", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("follow up", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("follow-up", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("rejection", StringComparison.OrdinalIgnoreCase);
-    }
-
     private void UpsertReviewDecision(IDictionary<string, GmailReviewDecision> decisions, string ownerUserId, string threadId, string decision, int? jobApplicationId, string? note)
     {
         if (!decisions.TryGetValue(threadId, out var existing))
@@ -1065,9 +964,11 @@ public sealed class GmailController : ControllerBase
         existing.UpdatedAt = DateTimeOffset.UtcNow;
     }
 
-    private void UpsertReviewDecision(List<GmailReviewDecision> decisions, string ownerUserId, string threadId, string decision, int? jobApplicationId, string? note)
+    // Single-thread upsert: callers acting on exactly one ThreadId should load just that row
+    // (see the FirstOrDefaultAsync call sites below) rather than every review decision for the
+    // owner just to scan for one match.
+    private void UpsertReviewDecision(GmailReviewDecision? existing, string ownerUserId, string threadId, string decision, int? jobApplicationId, string? note)
     {
-        var existing = decisions.FirstOrDefault(x => x.ThreadId == threadId);
         if (existing is null)
         {
             existing = new GmailReviewDecision
@@ -1075,7 +976,6 @@ public sealed class GmailController : ControllerBase
                 OwnerUserId = ownerUserId,
                 ThreadId = threadId,
             };
-            decisions.Add(existing);
             _db.GmailReviewDecisions.Add(existing);
         }
 
@@ -1085,54 +985,6 @@ public sealed class GmailController : ControllerBase
         existing.UpdatedAt = DateTimeOffset.UtcNow;
     }
 
-    private static string ToConfidence(int score)
-    {
-        return score switch
-        {
-            >= 30 => "high",
-            >= 16 => "medium",
-            _ => "low"
-        };
-    }
-
-    private static string? ExtractFirstEmail(string? value)
-    {
-        if (string.IsNullOrWhiteSpace(value)) return null;
-        var match = System.Text.RegularExpressions.Regex.Match(value, @"[A-Z0-9._%+-]+@[A-Z0-9.-]+\.[A-Z]{2,}", System.Text.RegularExpressions.RegexOptions.IgnoreCase);
-        return match.Success ? match.Value : null;
-    }
-
-    private static string? ExtractRecruiterName(string? value)
-    {
-        if (string.IsNullOrWhiteSpace(value)) return null;
-        var trimmed = value.Split('<')[0].Trim().Trim('"');
-        return string.IsNullOrWhiteSpace(trimmed) || trimmed.Contains('@') ? null : trimmed;
-    }
-
-    private static string? ExtractCompanyName(string? from, string? subject)
-    {
-        var subjectText = (subject ?? string.Empty).Trim();
-        if (!string.IsNullOrWhiteSpace(subjectText))
-        {
-            var parts = subjectText.Split(new[] { '-', '–', '|' }, StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries);
-            if (parts.Length >= 2) return parts[0];
-        }
-
-        var recruiterName = ExtractRecruiterName(from);
-        return recruiterName is { Length: > 0 } && recruiterName.Contains(' ') ? recruiterName.Split(' ').Last() : null;
-    }
-
-    private static string? ExtractRoleFromSubject(string? subject)
-    {
-        if (string.IsNullOrWhiteSpace(subject)) return null;
-        var trimmed = subject.Trim();
-        if (trimmed.Contains("interview", StringComparison.OrdinalIgnoreCase))
-        {
-            return trimmed.Replace("interview", string.Empty, StringComparison.OrdinalIgnoreCase).Trim(' ', '-', ':');
-        }
-        return trimmed.Length <= 120 ? trimmed : trimmed[..120];
-    }
-
     private string GetRequiredOwnerUserId()
     {
         return User.FindFirstValue(ClaimTypes.NameIdentifier) ?? User.FindFirstValue("sub")
@@ -1167,29 +1019,4 @@ public sealed class GmailController : ControllerBase
         return $"{Request.Scheme}://{Request.Host}/api/gmail/oauth/callback";
     }
 
-    private static string BuildPopupHtml(bool success, string message)
-    {
-        var escaped = System.Net.WebUtility.HtmlEncode(message);
-        var status = success ? "connected" : "error";
-        var title = success ? "Gmail connected" : "Gmail connection failed";
-        var serializedMessage = System.Text.Json.JsonSerializer.Serialize(message);
-        return $@"<!doctype html>
-<html>
-<head>
-  <meta charset=""utf-8"" />
-  <title>Gmail connection</title>
-</head>
-<body style=""font-family:Segoe UI,Arial,sans-serif;padding:24px;line-height:1.5;"">
-  <h2>{title}</h2>
-  <p>{escaped}</p>
-  <p>You can close this window.</p>
-  <script>
-    if (window.opener) {{
-      window.opener.postMessage({{ source: 'jobtracker-gmail-oauth', status: '{status}', message: {serializedMessage} }}, '*');
-    }}
-    window.close();
-  </script>
-</body>
-</html>";
-    }
 }

JobTrackerApi/Controllers/GmailDtos.cs

@@ -0,0 +1,79 @@
+using JobTrackerApi.Models;
+
+namespace JobTrackerApi.Controllers;
+
+// DTOs for GmailController, split out for readability (Wave 2 safe refactor -- no behaviour
+// change; these were previously nested inline in the controller file).
+public partial class GmailController
+{
+    public sealed record GmailImportResultDto(int Imported, int Skipped, string? ThreadId);
+    public sealed record GmailImportMessageResultDto(int Imported, int Skipped, string MessageId, string? ThreadId, Correspondence? Message);
+    public sealed record ImportGmailMessageRequest(int JobApplicationId, string MessageId);
+    public sealed record ImportGmailThreadRequest(int JobApplicationId, string ThreadId, string[] MessageIds);
+    public sealed record RefreshLinkedThreadsRequest(int JobApplicationId);
+    public sealed record GmailThreadRefreshThreadDto(string ThreadId, int Imported, int Skipped, int TotalMessages, string Status, DateTimeOffset? LatestMessageDate);
+    public sealed record GmailThreadRefreshResultDto(int JobApplicationId, int ThreadsChecked, int Imported, int Skipped, bool HasLinkedThreads, DateTimeOffset RefreshedAt, IReadOnlyList<GmailThreadRefreshThreadDto> Threads);
+    public sealed record GmailJobMatchReasonDto(string Label, string Value, int Points);
+    public sealed record GmailJobMatchedMessageDto(
+        string Id,
+        string ThreadId,
+        string Subject,
+        string From,
+        string To,
+        DateTimeOffset? Date,
+        string Snippet,
+        int Score,
+        string Confidence,
+        bool AlreadyImported,
+        IReadOnlyList<string> MatchedQueries,
+        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons);
+    public sealed record GmailJobMatchedThreadDto(
+        string ThreadId,
+        string Subject,
+        int Score,
+        string Confidence,
+        bool HasImportedMessages,
+        int ImportedMessageCount,
+        int MessageCount,
+        DateTimeOffset? LatestDate,
+        IReadOnlyList<string> MatchedQueries,
+        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons,
+        IReadOnlyList<GmailJobMatchedMessageDto> Messages);
+    public sealed record GmailJobMatchesResponseDto(
+        int JobApplicationId,
+        string JobTitle,
+        string CompanyName,
+        string? RecruiterName,
+        string? RecruiterEmail,
+        IReadOnlyList<string> Queries,
+        int CandidateMessageCount,
+        int CandidateThreadCount,
+        IReadOnlyList<GmailJobMatchedThreadDto> Threads);
+
+    public sealed record GmailReviewJobCandidateDto(int JobApplicationId, string JobTitle, string CompanyName, int Score, string Confidence, IReadOnlyList<GmailJobMatchReasonDto> Reasons);
+    public sealed record GmailReviewThreadDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, int MessageCount, string Routing, bool HasImportedMessages, string? DecisionNote, IReadOnlyList<string> MatchedQueries, IReadOnlyList<GmailReviewJobCandidateDto> JobCandidates, IReadOnlyList<GmailJobMatchedMessageDto> Messages);
+    public sealed record GmailReviewQueueResponseDto(IReadOnlyList<string> Queries, int CandidateThreadCount, int AutoLinkThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, IReadOnlyList<GmailReviewThreadDto> Threads);
+    public sealed record SaveGmailReviewDecisionRequest(string ThreadId, string Decision, int? JobApplicationId, string? Note);
+    public sealed record GmailManualSyncRequest(int? LookbackDays, int? MaxResultsPerQuery, bool? AutoImportHighConfidence, bool? IncludeSpamTrash);
+    public sealed record GmailManualSyncResultDto(int QueriesRun, int CandidateThreadCount, int AutoLinkedThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, int ImportedMessages, int ImportedThreads, int SkippedMessages, int LookbackDays, bool IncludeSpamTrash, DateTimeOffset SyncedAt);
+    public sealed record GmailSuggestedJobCandidateDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, string? CompanyName, string? RecruiterName, string? RecruiterEmail, string? SuggestedJobTitle, string Routing, IReadOnlyList<string> MatchedQueries, string Preview);
+    public sealed record GmailSuggestedJobsResponseDto(int Count, IReadOnlyList<GmailSuggestedJobCandidateDto> Items);
+    public sealed record CreateSuggestedGmailJobRequest(string ThreadId, string CompanyName, string JobTitle, string? RecruiterName, string? RecruiterEmail, string? Notes, string? Status);
+    public sealed record CreatedSuggestedGmailJobDto(int JobApplicationId, int CompanyId, string ThreadId, int Imported, int Skipped);
+    public sealed record RelinkGmailThreadRequest(int JobApplicationId, string ThreadId, bool RemoveFromOtherJobs, string? Note);
+    public sealed record GmailRelinkResultDto(string ThreadId, int JobApplicationId, int Imported, int Skipped, int UnlinkedMessages);
+    public sealed record UnlinkGmailThreadRequest(int JobApplicationId, string ThreadId, string? Note, string? NextDecision);
+    public sealed record GmailUnlinkResultDto(string ThreadId, int JobApplicationId, int RemovedMessages, string Decision);
+
+    public sealed record GmailConnectionStatusDto(
+        bool Connected,
+        string? GmailAddress,
+        DateTimeOffset? ConnectedAt,
+        DateTimeOffset? LastSyncedAt,
+        DateTimeOffset? LastSyncAttemptedAt,
+        DateTimeOffset? LastSyncSucceededAt,
+        string? LastSyncMode,
+        string? LastSyncSource,
+        string? LastSyncStatus,
+        string? LastSyncError);
+}

JobTrackerApi/Controllers/GmailParsing.cs

@@ -0,0 +1,116 @@
+using JobTrackerApi.Services;
+
+namespace JobTrackerApi.Controllers;
+
+// Pure parsing/formatting helpers for GmailController, split out for readability (Wave 2 safe
+// refactor -- no behaviour change). All are static and side-effect free.
+public sealed partial class GmailController
+{
+    private static string ApplySyncBoundary(string query, int lookbackDays, bool includeSpamTrash)
+    {
+        var bounded = (query ?? string.Empty).Trim();
+        if (!bounded.Contains("newer_than:", StringComparison.OrdinalIgnoreCase))
+        {
+            bounded = string.IsNullOrWhiteSpace(bounded)
+                ? $"newer_than:{lookbackDays}d"
+                : $"{bounded} newer_than:{lookbackDays}d";
+        }
+
+        if (!includeSpamTrash)
+        {
+            if (!bounded.Contains("in:spam", StringComparison.OrdinalIgnoreCase)) bounded += " -in:spam";
+            if (!bounded.Contains("in:trash", StringComparison.OrdinalIgnoreCase)) bounded += " -in:trash";
+        }
+
+        return bounded.Trim();
+    }
+
+    private static bool LooksLikeJobRelatedThread(IReadOnlyList<GmailQueryMatchedMessage> orderedMessages)
+    {
+        var sample = string.Join("\n", orderedMessages.Select(item => string.Join(" ", new[] { item.Message.Subject, item.Message.From, item.Message.Snippet }.Where(value => !string.IsNullOrWhiteSpace(value)))));
+        if (string.IsNullOrWhiteSpace(sample)) return false;
+        return sample.Contains("interview", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("application", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("recruit", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("role", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("position", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("offer", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("follow up", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("follow-up", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("rejection", StringComparison.OrdinalIgnoreCase);
+    }
+
+    private static string ToConfidence(int score)
+    {
+        return score switch
+        {
+            >= 30 => "high",
+            >= 16 => "medium",
+            _ => "low"
+        };
+    }
+
+    private static string? ExtractFirstEmail(string? value)
+    {
+        if (string.IsNullOrWhiteSpace(value)) return null;
+        var match = System.Text.RegularExpressions.Regex.Match(value, @"[A-Z0-9._%+-]+@[A-Z0-9.-]+\.[A-Z]{2,}", System.Text.RegularExpressions.RegexOptions.IgnoreCase);
+        return match.Success ? match.Value : null;
+    }
+
+    private static string? ExtractRecruiterName(string? value)
+    {
+        if (string.IsNullOrWhiteSpace(value)) return null;
+        var trimmed = value.Split('<')[0].Trim().Trim('"');
+        return string.IsNullOrWhiteSpace(trimmed) || trimmed.Contains('@') ? null : trimmed;
+    }
+
+    private static string? ExtractCompanyName(string? from, string? subject)
+    {
+        var subjectText = (subject ?? string.Empty).Trim();
+        if (!string.IsNullOrWhiteSpace(subjectText))
+        {
+            var parts = subjectText.Split(new[] { '-', '–', '|' }, StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries);
+            if (parts.Length >= 2) return parts[0];
+        }
+
+        var recruiterName = ExtractRecruiterName(from);
+        return recruiterName is { Length: > 0 } && recruiterName.Contains(' ') ? recruiterName.Split(' ').Last() : null;
+    }
+
+    private static string? ExtractRoleFromSubject(string? subject)
+    {
+        if (string.IsNullOrWhiteSpace(subject)) return null;
+        var trimmed = subject.Trim();
+        if (trimmed.Contains("interview", StringComparison.OrdinalIgnoreCase))
+        {
+            return trimmed.Replace("interview", string.Empty, StringComparison.OrdinalIgnoreCase).Trim(' ', '-', ':');
+        }
+        return trimmed.Length <= 120 ? trimmed : trimmed[..120];
+    }
+
+    private static string BuildPopupHtml(bool success, string message)
+    {
+        var escaped = System.Net.WebUtility.HtmlEncode(message);
+        var status = success ? "connected" : "error";
+        var title = success ? "Gmail connected" : "Gmail connection failed";
+        var serializedMessage = System.Text.Json.JsonSerializer.Serialize(message);
+        return $@"<!doctype html>
+<html>
+<head>
+  <meta charset=""utf-8"" />
+  <title>Gmail connection</title>
+</head>
+<body style=""font-family:Segoe UI,Arial,sans-serif;padding:24px;line-height:1.5;"">
+  <h2>{title}</h2>
+  <p>{escaped}</p>
+  <p>You can close this window.</p>
+  <script>
+    if (window.opener) {{
+      window.opener.postMessage({{ source: 'jobtracker-gmail-oauth', status: '{status}', message: {serializedMessage} }}, '*');
+    }}
+    window.close();
+  </script>
+</body>
+</html>";
+    }
+}

JobTrackerApi/Controllers/JobApplicationsController.cs

@@ -1376,11 +1376,7 @@ Canonical profile:
             string? CoverLetterText,
             string? JobUrl,
             DateTime? DateApplied,
-            DateTime? FeedbackRequestedAt,
-            bool? HasResume,
-            bool? HasCoverLetter,
-            bool? HasPortfolio,
-            bool? HasOtherAttachment
+            DateTime? FeedbackRequestedAt
         );
 
         private static (decimal? Min, decimal? Max, string? Currency, string? Period) NormalizeSalary(
@@ -1422,10 +1418,9 @@ Canonical profile:
                 NextAction = string.IsNullOrWhiteSpace(request.NextAction) ? null : request.NextAction.Trim(),
                 FollowUpAt = request.FollowUpAt,
                 FeedbackRequestedAt = request.FeedbackRequestedAt,
-                HasResume = request.HasResume ?? false,
-                HasCoverLetter = request.HasCoverLetter ?? false,
-                HasPortfolio = request.HasPortfolio ?? false,
-                HasOtherAttachment = request.HasOtherAttachment ?? false,
+                // HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived from
+                // Attachment rows (see AttachmentsController.RecomputeAttachmentFlagsAsync), not
+                // settable here -- they start false and get set correctly once files are uploaded.
                 Notes = string.IsNullOrWhiteSpace(request.Notes) ? null : request.Notes,
                 Description = string.IsNullOrWhiteSpace(request.Description) ? null : request.Description,
                 TranslatedDescription = string.IsNullOrWhiteSpace(request.TranslatedDescription) ? null : request.TranslatedDescription,
@@ -1486,10 +1481,6 @@ Canonical profile:
             string? SalaryPeriod,
             string? NextAction,
             DateTime? FollowUpAt,
-            bool? HasResume,
-            bool? HasCoverLetter,
-            bool? HasPortfolio,
-            bool? HasOtherAttachment,
             string? Notes,
             string? Description,
             string? TranslatedDescription,
@@ -1529,10 +1520,8 @@ Canonical profile:
             job.NextAction = string.IsNullOrWhiteSpace(request.NextAction) ? null : request.NextAction.Trim();
             job.FollowUpAt = request.FollowUpAt;
             job.FeedbackRequestedAt = request.FeedbackRequestedAt;
-            if (request.HasResume is not null) job.HasResume = request.HasResume.Value;
-            if (request.HasCoverLetter is not null) job.HasCoverLetter = request.HasCoverLetter.Value;
-            if (request.HasPortfolio is not null) job.HasPortfolio = request.HasPortfolio.Value;
-            if (request.HasOtherAttachment is not null) job.HasOtherAttachment = request.HasOtherAttachment.Value;
+            // HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived from
+            // Attachment rows, not settable here -- see AttachmentsController.RecomputeAttachmentFlagsAsync.
             job.Notes = request.Notes;
             job.Description = request.Description;
             job.TranslatedDescription = request.TranslatedDescription;

JobTrackerApi/Program.cs

@@ -162,6 +162,7 @@ builder.Services.AddSingleton<IJobCvMatchService, JobCvMatchService>();
 builder.Services.AddSingleton<ICvAiClassifier, CvAiClassifier>();
 builder.Services.AddSingleton<ICvAiNormalizer, CvAiNormalizer>();
 builder.Services.AddSingleton<IGoogleTokenValidator, GoogleTokenValidator>();
+builder.Services.AddSingleton<IMicrosoftTokenValidator, MicrosoftTokenValidator>();
 builder.Services.AddScoped<IGmailOAuthService, GmailOAuthService>();
 builder.Services.AddSingleton<IGmailJobMatchingService, GmailJobMatchingService>();
 builder.Services.AddSingleton<IGmailCorrespondenceEnrichmentService, NoOpGmailCorrespondenceEnrichmentService>();
@@ -209,6 +210,7 @@ builder.Services.AddScoped<JobImportService>();
 
 var requireAuth = builder.Configuration.GetValue("Auth:Require", false);
 var googleClientId = (builder.Configuration["Auth:GoogleClientId"] ?? "").Trim();
+var microsoftClientId = (builder.Configuration["Auth:MicrosoftClientId"] ?? "").Trim();
 
 var jwtKey = (builder.Configuration["Auth:JwtKey"] ?? "").Trim();
 var ephemeralJwtKey = false;
@@ -234,7 +236,7 @@ builder.Services.AddAuthentication(options =>
     {
         options.ForwardDefaultSelector = ctx =>
         {
-            if (string.IsNullOrWhiteSpace(googleClientId))
+            if (string.IsNullOrWhiteSpace(googleClientId) && string.IsNullOrWhiteSpace(microsoftClientId))
                 return "local";
 
             var auth = ctx.Request.Headers.Authorization.ToString();
@@ -250,9 +252,11 @@ builder.Services.AddAuthentication(options =>
             {
                 var jwt = handler.ReadJwtToken(token);
                 var iss = jwt.Issuer ?? "";
-                return iss is "accounts.google.com" or "https://accounts.google.com"
-                    ? "google"
-                    : "local";
+                if (!string.IsNullOrWhiteSpace(googleClientId) && iss is "accounts.google.com" or "https://accounts.google.com")
+                    return "google";
+                if (!string.IsNullOrWhiteSpace(microsoftClientId) && iss.StartsWith("https://login.microsoftonline.com/", StringComparison.OrdinalIgnoreCase))
+                    return "microsoft";
+                return "local";
             }
             catch
             {
@@ -322,6 +326,23 @@ if (!string.IsNullOrWhiteSpace(googleClientId))
     });
 }
 
+if (!string.IsNullOrWhiteSpace(microsoftClientId))
+{
+    builder.Services.AddAuthentication().AddJwtBearer("microsoft", options =>
+    {
+        // Validate Microsoft (Entra ID / personal account) ID tokens as bearer tokens.
+        // "common" authority + ValidateIssuer=false: multi-tenant issuer varies per tenant id.
+        options.Authority = "https://login.microsoftonline.com/common/v2.0";
+        options.TokenValidationParameters = new TokenValidationParameters
+        {
+            ValidateIssuer = false,
+            ValidateAudience = true,
+            ValidAudience = microsoftClientId,
+            ValidateLifetime = true,
+        };
+    });
+}
+
 builder.Services.AddAuthorization(options =>
 {
     if (requireAuth)

JobTrackerApi/Services/MicrosoftTokenValidator.cs

@@ -0,0 +1,100 @@
+using System.IdentityModel.Tokens.Jwt;
+using System.Security.Claims;
+using Microsoft.IdentityModel.Protocols;
+using Microsoft.IdentityModel.Protocols.OpenIdConnect;
+using Microsoft.IdentityModel.Tokens;
+
+namespace JobTrackerApi.Services;
+
+public sealed record MicrosoftTokenPrincipal(string Subject, string? Email, bool EmailVerified, string? GivenName, string? FamilyName, string? Name);
+
+public interface IMicrosoftTokenValidator
+{
+    Task<MicrosoftTokenPrincipal> ValidateAsync(string idToken, CancellationToken cancellationToken = default);
+}
+
+public sealed class MicrosoftTokenValidator : IMicrosoftTokenValidator
+{
+    private readonly IConfiguration _cfg;
+    private readonly IConfigurationManager<OpenIdConnectConfiguration> _configManager;
+
+    public MicrosoftTokenValidator(IConfiguration cfg)
+    {
+        _cfg = cfg;
+        // "common" endpoint: accepts both personal Microsoft accounts and work/school (Entra ID) tenants.
+        _configManager = new ConfigurationManager<OpenIdConnectConfiguration>(
+            "https://login.microsoftonline.com/common/v2.0/.well-known/openid-configuration",
+            new OpenIdConnectConfigurationRetriever());
+    }
+
+    public MicrosoftTokenValidator(IConfiguration cfg, IConfigurationManager<OpenIdConnectConfiguration> configManager)
+    {
+        _cfg = cfg;
+        _configManager = configManager;
+    }
+
+    public async Task<MicrosoftTokenPrincipal> ValidateAsync(string idToken, CancellationToken cancellationToken = default)
+    {
+        var audience = (_cfg["Auth:MicrosoftClientId"] ?? "").Trim();
+        if (string.IsNullOrWhiteSpace(audience))
+        {
+            throw new InvalidOperationException("Microsoft sign-in is not configured.");
+        }
+
+        var config = await _configManager.GetConfigurationAsync(cancellationToken);
+        var handler = new JwtSecurityTokenHandler
+        {
+            // The handler's default inbound claim map rewrites "oid"/"tid" to long Microsoft
+            // schema URIs (an AAD-specific quirk not shared by Google's OIDC claims) -- keep
+            // claim names as issued so FindFirst("oid") below actually matches.
+            MapInboundClaims = false,
+        };
+        // ponytail: multi-tenant "common" app -- each tenant's issuer embeds its own tenant id
+        // (https://login.microsoftonline.com/{tenantId}/v2.0), so issuer is checked by shape below
+        // rather than pinned to one value. Signature/audience/lifetime are still fully validated.
+        var principal = handler.ValidateToken(idToken, new TokenValidationParameters
+        {
+            ValidateIssuer = false,
+            ValidateAudience = true,
+            ValidAudience = audience,
+            ValidateLifetime = true,
+            ValidateIssuerSigningKey = true,
+            IssuerSigningKeys = config.SigningKeys,
+            ClockSkew = TimeSpan.FromMinutes(2),
+        }, out var validatedToken);
+
+        var issuer = (validatedToken as JwtSecurityToken)?.Issuer ?? principal.FindFirst("iss")?.Value ?? "";
+        if (!IsMicrosoftIssuer(issuer))
+        {
+            throw new InvalidOperationException("Microsoft token has an unexpected issuer.");
+        }
+
+        var subject = principal.FindFirst("oid")?.Value?.Trim()
+            ?? principal.FindFirst(JwtRegisteredClaimNames.Sub)?.Value?.Trim()
+            ?? principal.FindFirst(ClaimTypes.NameIdentifier)?.Value?.Trim();
+        if (string.IsNullOrWhiteSpace(subject))
+        {
+            throw new InvalidOperationException("Microsoft token is missing a subject.");
+        }
+
+        var email = principal.FindFirst("email")?.Value?.Trim()
+            ?? principal.FindFirst(ClaimTypes.Email)?.Value?.Trim()
+            ?? principal.FindFirst("preferred_username")?.Value?.Trim();
+
+        return new MicrosoftTokenPrincipal(
+            Subject: subject,
+            Email: email,
+            // Microsoft ID tokens don't carry an email_verified claim; presence of an email claim
+            // from a signature-validated token is treated as verified, same trust level Microsoft's
+            // own APIs give it.
+            EmailVerified: !string.IsNullOrWhiteSpace(email),
+            GivenName: principal.FindFirst("given_name")?.Value?.Trim(),
+            FamilyName: principal.FindFirst("family_name")?.Value?.Trim(),
+            Name: principal.FindFirst("name")?.Value?.Trim() ?? principal.Identity?.Name?.Trim()
+        );
+    }
+
+    private static bool IsMicrosoftIssuer(string issuer)
+        => issuer.StartsWith("https://login.microsoftonline.com/", StringComparison.OrdinalIgnoreCase)
+            && issuer.EndsWith("/v2.0", StringComparison.OrdinalIgnoreCase);
+}

JobTrackerApi/Services/StartupInitializationExtensions.cs

@@ -241,6 +241,9 @@ public static class StartupInitializationExtensions
             `GoogleSubject` longtext NULL,
             `GoogleEmail` longtext NULL,
             `GoogleLinkedAt` datetime(6) NULL,
+            `MicrosoftSubject` longtext NULL,
+            `MicrosoftEmail` longtext NULL,
+            `MicrosoftLinkedAt` datetime(6) NULL,
             PRIMARY KEY (`Id`)
         ) CHARACTER SET=utf8mb4;
 
@@ -353,7 +356,10 @@ public static class StartupInitializationExtensions
             "AvatarImageDataUrl" TEXT NULL,
             "GoogleSubject" TEXT NULL,
             "GoogleEmail" TEXT NULL,
-            "GoogleLinkedAt" TEXT NULL
+            "GoogleLinkedAt" TEXT NULL,
+            "MicrosoftSubject" TEXT NULL,
+            "MicrosoftEmail" TEXT NULL,
+            "MicrosoftLinkedAt" TEXT NULL
         );
         """);
 
@@ -431,6 +437,9 @@ public static class StartupInitializationExtensions
                 EnsureColumn(conn, "AspNetUsers", "GoogleSubject", "ALTER TABLE AspNetUsers ADD COLUMN GoogleSubject TEXT NULL;");
                 EnsureColumn(conn, "AspNetUsers", "GoogleEmail", "ALTER TABLE AspNetUsers ADD COLUMN GoogleEmail TEXT NULL;");
                 EnsureColumn(conn, "AspNetUsers", "GoogleLinkedAt", "ALTER TABLE AspNetUsers ADD COLUMN GoogleLinkedAt TEXT NULL;");
+                EnsureColumn(conn, "AspNetUsers", "MicrosoftSubject", "ALTER TABLE AspNetUsers ADD COLUMN MicrosoftSubject TEXT NULL;");
+                EnsureColumn(conn, "AspNetUsers", "MicrosoftEmail", "ALTER TABLE AspNetUsers ADD COLUMN MicrosoftEmail TEXT NULL;");
+                EnsureColumn(conn, "AspNetUsers", "MicrosoftLinkedAt", "ALTER TABLE AspNetUsers ADD COLUMN MicrosoftLinkedAt TEXT NULL;");
 
                 static void EnsureUserRuleSettingsTable(DbConnection c)
                 {
@@ -757,6 +766,9 @@ public static class StartupInitializationExtensions
                     EnsureMySqlColumn(conn, "AspNetUsers", "GoogleSubject", "ALTER TABLE `AspNetUsers` ADD COLUMN `GoogleSubject` longtext NULL;");
                     EnsureMySqlColumn(conn, "AspNetUsers", "GoogleEmail", "ALTER TABLE `AspNetUsers` ADD COLUMN `GoogleEmail` longtext NULL;");
                     EnsureMySqlColumn(conn, "AspNetUsers", "GoogleLinkedAt", "ALTER TABLE `AspNetUsers` ADD COLUMN `GoogleLinkedAt` datetime NULL;");
+                    EnsureMySqlColumn(conn, "AspNetUsers", "MicrosoftSubject", "ALTER TABLE `AspNetUsers` ADD COLUMN `MicrosoftSubject` longtext NULL;");
+                    EnsureMySqlColumn(conn, "AspNetUsers", "MicrosoftEmail", "ALTER TABLE `AspNetUsers` ADD COLUMN `MicrosoftEmail` longtext NULL;");
+                    EnsureMySqlColumn(conn, "AspNetUsers", "MicrosoftLinkedAt", "ALTER TABLE `AspNetUsers` ADD COLUMN `MicrosoftLinkedAt` datetime NULL;");
 
                     if (!HasMySqlTable(conn, "RuleSettings"))
                     {

JobTrackerApi/appsettings.Development.json

@@ -26,7 +26,8 @@
     "JwtExpiresMinutes": 720,
     "AdminEmail": "admin@example.com",
     "AdminPassword": "CHANGE_ME_STRONG_DEV_PASSWORD",
-    "GoogleClientId": "CHANGE_ME_GOOGLE_CLIENT_ID"
+    "GoogleClientId": "CHANGE_ME_GOOGLE_CLIENT_ID",
+    "MicrosoftClientId": "CHANGE_ME_MICROSOFT_CLIENT_ID"
   },
   "App": {
     "PublicBaseUrl": "https://jobs.cesnimda.uk"

Models/ApplicationUser.cs

@@ -16,4 +16,7 @@ public sealed class ApplicationUser : IdentityUser
     public string? GoogleSubject { get; set; }
     public string? GoogleEmail { get; set; }
     public DateTimeOffset? GoogleLinkedAt { get; set; }
+    public string? MicrosoftSubject { get; set; }
+    public string? MicrosoftEmail { get; set; }
+    public DateTimeOffset? MicrosoftLinkedAt { get; set; }
 }

Models/JobApplication.cs

@@ -24,7 +24,9 @@ public class JobApplication
     public DateTime? FeedbackRequestedAt { get; set; }
     public string? RecruiterMessageDraft { get; set; }
 
-    // Attachment checklist
+    // Attachment checklist. Derived from Attachment rows, not directly settable by API
+    // consumers -- see AttachmentsController.RecomputeAttachmentFlagsAsync, the single place
+    // these are written, so they can't drift from what's actually attached.
     public bool HasResume { get; set; } = false;
     public bool HasCoverLetter { get; set; } = false;
     public bool HasPortfolio { get; set; } = false;

job-tracker-ui/package-lock.json

@@ -8,6 +8,7 @@
       "name": "job-tracker-ui",
       "version": "0.1.0",
       "dependencies": {
+        "@azure/msal-browser": "^5.17.0",
         "@emotion/react": "^11.14.0",
         "@emotion/styled": "^11.14.1",
         "@mui/icons-material": "^7.3.9",
@@ -52,6 +53,27 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
+    "node_modules/@azure/msal-browser": {
+      "version": "5.17.0",
+      "resolved": "https://registry.npmjs.org/@azure/msal-browser/-/msal-browser-5.17.0.tgz",
+      "integrity": "sha512-/yTnW2TCk9Mh+2b/NOaHAN+MryUNxzRTaJD/YtrqOA9bpBWfTXn/iyReRbaLrK/btBo3stEzLyEvuWp2NZ5DuA==",
+      "license": "MIT",
+      "dependencies": {
+        "@azure/msal-common": "16.11.1"
+      },
+      "engines": {
+        "node": ">=0.8.0"
+      }
+    },
+    "node_modules/@azure/msal-common": {
+      "version": "16.11.1",
+      "resolved": "https://registry.npmjs.org/@azure/msal-common/-/msal-common-16.11.1.tgz",
+      "integrity": "sha512-yPohvMwWLv1XnaWnIUyKUh8CvcVChCGqG/VluGwfGmaAfrZTNt5yQ+sIs462Sgw6+e2K83KGmMJ860p73ZSCrw==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.8.0"
+      }
+    },
     "node_modules/@babel/code-frame": {
       "version": "7.29.0",
       "resolved": "https://registry.npmjs.org/@babel/code-frame/-/code-frame-7.29.0.tgz",

job-tracker-ui/package.json

@@ -3,6 +3,7 @@
   "version": "0.1.0",
   "private": true,
   "dependencies": {
+    "@azure/msal-browser": "^5.17.0",
     "@emotion/react": "^11.14.0",
     "@emotion/styled": "^11.14.1",
     "@mui/icons-material": "^7.3.9",

job-tracker-ui/src/components/AddJobModal.tsx

@@ -327,10 +327,6 @@ export default function AddJobModal({ open, onClose, onCreated, initialUrl }: Pr
         notes,
         coverLetterText: null,
         dateApplied,
-        hasResume: attachments.resume.length > 0,
-        hasCoverLetter: attachments.coverLetter.length > 0,
-        hasPortfolio: attachments.portfolio.length > 0,
-        hasOtherAttachment: attachments.other.length > 0,
       });
 
       if (response.data?.id && attachmentCount > 0) {

job-tracker-ui/src/components/EditJobDialog.tsx

@@ -158,10 +158,6 @@ export default function EditJobDialog({ open, jobId, onClose, onSaved }: Props)
         salaryPeriod: salaryPeriod || null,
         nextAction: nextAction.trim() || null,
         followUpAt: followUpAt || null,
-        hasResume,
-        hasCoverLetter,
-        hasPortfolio,
-        hasOtherAttachment,
         notes: notes || null,
         description: description || null,
         translatedDescription: translatedDescription || null,
@@ -243,16 +239,13 @@ export default function EditJobDialog({ open, jobId, onClose, onSaved }: Props)
 
           <Paper variant="outlined" sx={{ p: 2 }}>
             <Typography variant="overline" sx={{ color: "text.secondary" }}>{t("editJobAttachmentsChecklist")}</Typography>
-            <Box sx={{ display: "flex", gap: 1, flexWrap: "wrap", mt: 1, mb: 1.5 }}>
+            {/* Derived from actual uploaded attachments (see the Attachments panel) -- not
+                manually editable, so this can never drift from what's really attached. */}
+            <Box sx={{ display: "flex", gap: 1, flexWrap: "wrap", mt: 1 }}>
               <Chip size="small" label={hasResume ? t("editJobResumeReady") : t("editJobResumeMissing")} color={hasResume ? "success" : "default"} variant={hasResume ? "filled" : "outlined"} />
               <Chip size="small" label={hasCoverLetter ? t("editJobCoverLetterReady") : t("editJobCoverLetterMissing")} color={hasCoverLetter ? "success" : "default"} variant={hasCoverLetter ? "filled" : "outlined"} />
               <Chip size="small" label={hasPortfolio ? t("editJobPortfolioReady") : t("editJobPortfolioOptional")} color={hasPortfolio ? "success" : "default"} variant={hasPortfolio ? "filled" : "outlined"} />
-            </Box>
-            <Box sx={{ display: "flex", gap: 2, flexWrap: "wrap", mt: 1 }}>
-              <FormControlLabel control={<Checkbox checked={hasResume} onChange={(e) => setHasResume(e.target.checked)} />} label={t("editJobResume")} />
-              <FormControlLabel control={<Checkbox checked={hasCoverLetter} onChange={(e) => setHasCoverLetter(e.target.checked)} />} label={t("editJobCoverLetter")} />
-              <FormControlLabel control={<Checkbox checked={hasPortfolio} onChange={(e) => setHasPortfolio(e.target.checked)} />} label={t("editJobPortfolio")} />
-              <FormControlLabel control={<Checkbox checked={hasOtherAttachment} onChange={(e) => setHasOtherAttachment(e.target.checked)} />} label={t("editJobOtherAttachment")} />
+              {hasOtherAttachment && <Chip size="small" label={t("editJobOtherAttachment")} color="success" variant="filled" />}
             </Box>
           </Paper>
         </Box>

job-tracker-ui/src/components/MicrosoftAuthCard.tsx

@@ -0,0 +1,185 @@
+import React, { useEffect, useState } from "react";
+
+import { Box, Button, Chip, Paper, Typography } from "@mui/material";
+import { PublicClientApplication } from "@azure/msal-browser";
+
+import { api, getApiErrorMessage } from "../api";
+import { clearAuthClientState, getAuthPersistencePreference } from "../auth";
+import { useToast } from "../toast";
+import { useI18n } from "../i18n/I18nProvider";
+
+type MeResponse = {
+  provider?: "local" | "google" | "microsoft" | "external";
+  email?: string;
+  userName?: string;
+  displayName?: string;
+  firstName?: string;
+  lastName?: string;
+  microsoftLink?: {
+    linked: boolean;
+    email?: string | null;
+    linkedAt?: string | null;
+  } | null;
+};
+
+let msalInstance: PublicClientApplication | null = null;
+function getMsalInstance(clientId: string): PublicClientApplication {
+  msalInstance ??= new PublicClientApplication({
+    auth: { clientId, authority: "https://login.microsoftonline.com/common", redirectUri: window.location.origin },
+  });
+  return msalInstance;
+}
+
+export default function MicrosoftAuthCard({ onSignedIn }: { onSignedIn?: () => void }) {
+  const { toast } = useToast();
+  const { t } = useI18n();
+  const [me, setMe] = useState<MeResponse | null>(null);
+  const [working, setWorking] = useState(false);
+
+  const clientId = (process.env.REACT_APP_MICROSOFT_CLIENT_ID || "").trim();
+  const signedIn = Boolean(me?.provider);
+  const actionLabel = !signedIn
+    ? t("continueWithMicrosoft")
+    : me?.provider === "local" && !me?.microsoftLink?.linked
+      ? t("linkWithMicrosoft")
+      : t("signInWithMicrosoft");
+
+  async function refreshMe() {
+    try {
+      const res = await api.get<MeResponse>("/auth/me");
+      setMe(res.data);
+    } catch {
+      setMe(null);
+    }
+  }
+
+  useEffect(() => {
+    void refreshMe();
+  }, []);
+
+  useEffect(() => {
+    const onAuthChanged = () => { void refreshMe(); };
+    window.addEventListener("auth-changed", onAuthChanged);
+    return () => window.removeEventListener("auth-changed", onAuthChanged);
+  }, []);
+
+  async function handleSignIn() {
+    if (!clientId) return;
+    setWorking(true);
+    try {
+      const msal = getMsalInstance(clientId);
+      await msal.initialize();
+      const result = await msal.loginPopup({ scopes: ["openid", "profile", "email"] });
+      const idToken = result.idToken;
+      if (!idToken) throw new Error(t("microsoftAuthFailed"));
+
+      if (me?.provider === "local") {
+        const res = await api.post<{ linked: boolean; email?: string | null }>("/auth/microsoft/link", { token: idToken, rememberMe: getAuthPersistencePreference() === "local" });
+        toast(res.data?.email ? t("microsoftLinkedSuccessWithEmail", { email: res.data.email }) : t("microsoftLinkedSuccess"), "success");
+        await refreshMe();
+      } else {
+        await api.post("/auth/microsoft/exchange", { token: idToken, rememberMe: getAuthPersistencePreference() === "local" });
+        window.dispatchEvent(new Event("auth-changed"));
+        toast(t("microsoftSignedIn"), "success");
+        onSignedIn?.();
+      }
+    } catch (e: any) {
+      toast(getApiErrorMessage(e, t("microsoftAuthFailed")), "error");
+    } finally {
+      setWorking(false);
+    }
+  }
+
+  const signedInName = me?.userName || me?.displayName || [me?.firstName, me?.lastName].filter(Boolean).join(" ") || me?.email || "";
+
+  return (
+    <Paper sx={{ mt: 2, p: 2 }}>
+      <Typography variant="h6" sx={{ mb: 1 }}>
+        {t("microsoftAccountTitle")}
+      </Typography>
+
+      {!clientId && (
+        <Typography sx={{ color: "text.secondary" }}>
+          {t("microsoftSetupHint")}
+        </Typography>
+      )}
+
+      {clientId && (
+        <Box sx={{ display: "flex", flexDirection: "column", gap: 1.25 }}>
+          <Box sx={{ display: "flex", gap: 1, flexWrap: "wrap" }}>
+            <Chip size="small" label={me?.microsoftLink?.linked ? t("microsoftLinked") : t("microsoftAvailableToLink")} color={me?.microsoftLink?.linked ? "success" : "default"} variant={me?.microsoftLink?.linked ? "filled" : "outlined"} />
+            {me?.microsoftLink?.linkedAt ? <Chip size="small" variant="outlined" label={t("microsoftLinkedDate", { date: new Date(me.microsoftLink.linkedAt).toLocaleDateString() })} /> : null}
+          </Box>
+
+          {!signedIn ? (
+            <Typography sx={{ color: "text.secondary" }}>
+              {t("microsoftSignInHint")}
+            </Typography>
+          ) : me?.provider === "local" ? (
+            <Typography sx={{ color: "text.secondary" }}>
+              {me.microsoftLink?.linked
+                ? t("microsoftLinkedTo", { email: me.microsoftLink.email || t("microsoftLinkedToYourAccount") })
+                : t("microsoftBindHint")}
+            </Typography>
+          ) : (
+            <Typography sx={{ color: "text.secondary" }}>
+              {t("microsoftExchangeHint")}
+            </Typography>
+          )}
+
+          <Box sx={{ display: "flex", flexDirection: "column", alignItems: "flex-start", gap: 1 }}>
+            <Typography variant="caption" sx={{ color: "text.secondary", fontWeight: 700, letterSpacing: 0.4, textTransform: "uppercase" }}>
+              {actionLabel}
+            </Typography>
+            <Button variant="outlined" disabled={working} onClick={() => void handleSignIn()}>
+              {actionLabel}
+            </Button>
+          </Box>
+
+          <Box sx={{ display: "flex", alignItems: "center", gap: 2, flexWrap: "wrap" }}>
+            {signedIn ? (
+              <Button
+                variant="outlined"
+                onClick={() => {
+                  void api.post("/auth/logout").catch(() => undefined).finally(() => {
+                    clearAuthClientState();
+                    setMe(null);
+                    toast(t("signedOut"), "info");
+                  });
+                }}
+              >
+                {t("signOut")}
+              </Button>
+            ) : null}
+
+            {me?.provider === "local" && me.microsoftLink?.linked ? (
+              <Button
+                variant="outlined"
+                color="warning"
+                disabled={working}
+                onClick={async () => {
+                  try {
+                    await api.delete("/auth/microsoft/link");
+                    toast(t("microsoftUnlinked"), "info");
+                    await refreshMe();
+                  } catch (e: any) {
+                    const msg = e?.response?.data || e?.message || t("microsoftUnlinkFailed");
+                    toast(String(msg), "error");
+                  }
+                }}
+              >
+                {t("unlinkMicrosoft")}
+              </Button>
+            ) : null}
+          </Box>
+
+          {signedIn && me?.email ? (
+            <Typography variant="body2" sx={{ color: "text.secondary" }}>
+              {t("signedInAs", { name: signedInName })}
+            </Typography>
+          ) : null}
+        </Box>
+      )}
+    </Paper>
+  );
+}

job-tracker-ui/src/i18n/translations.ts

@@ -628,6 +628,26 @@ export const translations = {
     googleScriptLoadFailed: "Google auth script failed to load.",
     googleUnlinked: "Google account unlinked.",
     googleUnlinkFailed: "Failed to unlink Google account.",
+    microsoftAccountTitle: "Microsoft account",
+    microsoftSetupHint: "Set `REACT_APP_MICROSOFT_CLIENT_ID` in your UI environment to enable Microsoft sign-in and account linking.",
+    microsoftLinked: "Linked",
+    microsoftAvailableToLink: "Available to link",
+    microsoftLinkedDate: "Linked {date}",
+    microsoftSignInHint: "Sign in with a Microsoft account that has already been linked to your Jobbjakt user.",
+    continueWithMicrosoft: "Continue with Microsoft",
+    signInWithMicrosoft: "Sign in with Microsoft",
+    linkWithMicrosoft: "Link with Microsoft",
+    microsoftLinkedTo: "Linked to {email}.",
+    microsoftLinkedToYourAccount: "Linked to your Microsoft account.",
+    microsoftBindHint: "Bind a Microsoft account to this user so you can sign in with Microsoft and still keep your normal app roles and data.",
+    microsoftExchangeHint: "Exchange your Microsoft sign-in for a normal Jobbjakt session.",
+    microsoftSignedIn: "Signed in with Microsoft.",
+    microsoftLinkedSuccess: "Microsoft account linked.",
+    microsoftLinkedSuccessWithEmail: "Linked Microsoft account {email}.",
+    microsoftAuthFailed: "Microsoft authentication failed.",
+    microsoftUnlinked: "Microsoft account unlinked.",
+    microsoftUnlinkFailed: "Failed to unlink Microsoft account.",
+    unlinkMicrosoft: "Unlink Microsoft",
     signedOut: "Signed out.",
     signedInAs: "Signed in as {name}.",
     unlinkGoogle: "Unlink Google",
@@ -663,6 +683,7 @@ export const translations = {
     authOptional: "Authentication is optional in this environment.",
     emailAndPassword: "Email & password",
     google: "Google",
+    microsoft: "Microsoft",
     createAccount: "Create account",
     signedIn: "Signed in.",
     rememberMe: "Remember me",
@@ -1572,6 +1593,26 @@ export const translations = {
     googleScriptLoadFailed: "Kunne ikke laste Google-autentiseringsskriptet.",
     googleUnlinked: "Google-konto koblet fra.",
     googleUnlinkFailed: "Kunne ikke koble fra Google-kontoen.",
+    microsoftAccountTitle: "Microsoft-konto",
+    microsoftSetupHint: "Sett `REACT_APP_MICROSOFT_CLIENT_ID` i UI-miljøet ditt for å aktivere Microsoft-innlogging og kontokobling.",
+    microsoftLinked: "Koblet",
+    microsoftAvailableToLink: "Tilgjengelig for kobling",
+    microsoftLinkedDate: "Koblet {date}",
+    microsoftSignInHint: "Logg inn med en Microsoft-konto som allerede er koblet til Jobbjakt-brukeren din.",
+    continueWithMicrosoft: "Fortsett med Microsoft",
+    signInWithMicrosoft: "Logg inn med Microsoft",
+    linkWithMicrosoft: "Koble til med Microsoft",
+    microsoftLinkedTo: "Koblet til {email}.",
+    microsoftLinkedToYourAccount: "Koblet til Microsoft-kontoen din.",
+    microsoftBindHint: "Koble en Microsoft-konto til denne brukeren slik at du kan logge inn med Microsoft og fortsatt beholde vanlige approller og data.",
+    microsoftExchangeHint: "Bytt Microsoft-innloggingen din mot en vanlig Jobbjakt-økt.",
+    microsoftSignedIn: "Logget inn med Microsoft.",
+    microsoftLinkedSuccess: "Microsoft-konto koblet.",
+    microsoftLinkedSuccessWithEmail: "Koblet Microsoft-konto {email}.",
+    microsoftAuthFailed: "Microsoft-autentisering mislyktes.",
+    microsoftUnlinked: "Microsoft-konto koblet fra.",
+    microsoftUnlinkFailed: "Kunne ikke koble fra Microsoft-kontoen.",
+    unlinkMicrosoft: "Koble fra Microsoft",
     signedOut: "Logget ut.",
     signedInAs: "Logget inn som {name}.",
     unlinkGoogle: "Koble fra Google",
@@ -1607,6 +1648,7 @@ export const translations = {
     authOptional: "Autentisering er valgfri i dette miljøet.",
     emailAndPassword: "E-post og passord",
     google: "Google",
+    microsoft: "Microsoft",
     createAccount: "Opprett konto",
     signedIn: "Logget inn.",
     rememberMe: "Husk meg",

job-tracker-ui/src/pages/LoginPage.tsx

@@ -7,12 +7,14 @@ import { useLocation, useNavigate } from "react-router-dom";
 import { api, getApiErrorMessage } from "../api";
 import { getRememberMePref, setAuthPersistencePreference } from "../auth";
 import GoogleAuthCard from "../components/GoogleAuthCard";
+import MicrosoftAuthCard from "../components/MicrosoftAuthCard";
 import { useToast } from "../toast";
 import { useI18n } from "../i18n/I18nProvider";
 
 type AuthConfig = {
   requireAuth: boolean;
   googleEnabled: boolean;
+  microsoftEnabled: boolean;
   localEnabled: boolean;
   allowRegistration: boolean;
 };
@@ -81,6 +83,7 @@ export default function LoginPage() {
         <Tabs value={tab} onChange={(_, v) => setTab(v)} sx={{ mb: 2 }}>
           <Tab label={t("emailAndPassword")} />
           <Tab label={t("google")} />
+          <Tab label={t("microsoft")} />
         </Tabs>
 
         {tab === 0 && (
@@ -123,6 +126,7 @@ export default function LoginPage() {
         )}
 
         {tab === 1 && <GoogleAuthCard onSignedIn={() => { navigate(nextPath, { replace: true }); }} />}
+        {tab === 2 && <MicrosoftAuthCard onSignedIn={() => { navigate(nextPath, { replace: true }); }} />}
       </Paper>
     </Box>
   );

job-tracker-ui/src/pages/ProfilePage.tsx

@@ -9,6 +9,7 @@ import ZoomInOutlinedIcon from "@mui/icons-material/ZoomInOutlined";
 
 import { api, getApiErrorMessage } from "../api";
 import GoogleAuthCard from "../components/GoogleAuthCard";
+import MicrosoftAuthCard from "../components/MicrosoftAuthCard";
 import CropImageDialog from "../components/CropImageDialog";
 import { useToast } from "../toast";
 import { useI18n } from "../i18n/I18nProvider";
@@ -562,6 +563,7 @@ export default function ProfilePage() {
       </Box>
 
       <GoogleAuthCard />
+      <MicrosoftAuthCard />
 
       <Box sx={{ mt: 3, display: "grid", gridTemplateColumns: { xs: "1fr", md: "1fr 1fr" }, gap: 2 }}>
         <Box sx={{ gridColumn: "1 / -1" }}>

job-tracker-ui/src/setupTests.ts

@@ -29,12 +29,13 @@ jest.mock('./api', () => ({
 }));
 
 jest.mock('./components/GoogleAuthCard', () => () => null);
+jest.mock('./components/MicrosoftAuthCard', () => () => null);
 
 beforeEach(() => {
   const { api } = require('./api');
   api.get.mockImplementation((url: string) => {
     if (url === '/auth/config') {
-      return Promise.resolve({ data: { requireAuth: false, googleEnabled: false, localEnabled: true, allowRegistration: false } });
+      return Promise.resolve({ data: { requireAuth: false, googleEnabled: false, microsoftEnabled: false, localEnabled: true, allowRegistration: false } });
     }
     if (url === '/auth/me') {
       return Promise.resolve({ data: { roles: [], email: 'demo@example.com', userName: 'demo' } });