fix(auth): app passwords now sign in SMTP, IMAP and POP3

The webmail creates app passwords (shown once, stored hashed, with scopes) but the protocol servers only compared a login against mailboxes.password_hash, so an app password was always refused with 535 / authentication failed. They exist because mail clients cannot do a second factor. - port.MailboxAuth carries the mailbox's app passwords (newest 20) with their scopes; the Postgres repository loads them and stamps last_used_at on use - verifyCredential accepts the mailbox password or an app password that holds the scope of the protocol; SMTP, IMAP and POP3 use it. ManageSieve keeps the mailbox password only, as no default scope covers it - a malformed app password hash is skipped instead of failing the login; a malformed mailbox hash still surfaces as the server-side error it was Tests: unit cases for scopes and malformed hashes, the three entry points, repository tests against Postgres, and an end-to-end test on the real submission server that fails with 535 without the fix and passes with it. Full `go test ./...` with TEST_DATABASE_URL, go vet and lang-lint are clean.
2026-10-16 09:21:08 -03:00
1 parent 8e7c0abd0a
commit 110a240cd9
@@ -15,8 +15,29 @@ type MailboxAuth struct {
 	DomainName   string
 	// MaxRecipientsPerHour caps a compromised account's blast radius.
 	MaxRecipientsPerHour int
+	// AppPasswords are the per-client credentials the user generated in the
+	// webmail. Protocol clients cannot answer a second factor, so these are how
+	// a mail client signs in on an account that has one.
+	AppPasswords []AppPasswordAuth
 }

+// AppPasswordAuth is one app password as stored: a hash, never the secret.
+type AppPasswordAuth struct {
+	ID     uuid.UUID
+	Hash   string
+	Scopes []string
+}
+
+// AppPasswordUseRecorder is implemented by repositories that can note when an
+// app password was last used. It is optional: a fake in a test need not have it.
+type AppPasswordUseRecorder interface {
+	RecordAppPasswordUse(ctx context.Context, id uuid.UUID) error
+}
+
+// MaxAppPasswordsChecked bounds how many app passwords one login attempt is
+// compared against.
+const MaxAppPasswordsChecked = 20
+
 // AuthRepository resolves a login address to its stored credential.
 type AuthRepository interface {
 	// FindByAddress returns nil, nil (not an error) when no active mailbox
@@ -0,0 +1,68 @@
+package usecase
+
+import (
+	"context"
+	"log/slog"
+
+	"github.com/alexedwards/argon2id"
+
+	"lambdamail/protocols/internal/application/port"
+)
+
+// Scopes an app password can be limited to. They match the values of
+// app_passwords.scopes, whose default is {imap,pop3,smtp}.
+const (
+	ScopeSMTP = "smtp"
+	ScopeIMAP = "imap"
+	ScopePOP3 = "pop3"
+)
+
+// verifyCredential reports whether password unlocks the mailbox for a client
+// of the given protocol: either the mailbox's own password, or one of its app
+// passwords that holds the scope.
+//
+// Before this, every protocol compared only against the mailbox password, so
+// an app password - created in the webmail precisely because a mail client
+// cannot answer a second factor - never worked anywhere.
+//
+// An error is returned only when the mailbox's own stored hash is unreadable
+// (a server-side fault, reported as before) and no app password matched. A
+// broken app password hash is skipped: it must not take the good ones, or a
+// plain wrong-password answer, down with it.
+func verifyCredential(ctx context.Context, repo port.AuthRepository, rec *port.MailboxAuth, password, scope string) (bool, error) {
+	match, mainErr := argon2id.ComparePasswordAndHash(password, rec.PasswordHash)
+	if mainErr == nil && match {
+		return true, nil
+	}
+
+	for _, app := range rec.AppPasswords {
+		if !hasScope(app.Scopes, scope) {
+			continue
+		}
+		ok, err := argon2id.ComparePasswordAndHash(password, app.Hash)
+		if err != nil || !ok {
+			continue
+		}
+		if recorder, can := repo.(port.AppPasswordUseRecorder); can {
+			// Best effort: a failed timestamp must not fail a login that succeeded
+			if err := recorder.RecordAppPasswordUse(ctx, app.ID); err != nil {
+				slog.Warn("record app password use", "error", err)
+			}
+		}
+		return true, nil
+	}
+
+	if mainErr != nil {
+		return false, mainErr
+	}
+	return false, nil
+}
+
+func hasScope(scopes []string, scope string) bool {
+	for _, s := range scopes {
+		if s == scope {
+			return true
+		}
+	}
+	return false
+}
@@ -0,0 +1,218 @@
+package usecase
+
+import (
+	"context"
+	"errors"
+	"testing"
+
+	"github.com/alexedwards/argon2id"
+	"github.com/google/uuid"
+
+	"lambdamail/protocols/internal/application/port"
+)
+
+// Light parameters: the tests check logic, not the cost of a real hash.
+var testArgon = &argon2id.Params{Memory: 8 * 1024, Iterations: 1, Parallelism: 1, SaltLength: 16, KeyLength: 32}
+
+func mustHash(t *testing.T, password string) string {
+	t.Helper()
+	hash, err := argon2id.CreateHash(password, testArgon)
+	if err != nil {
+		t.Fatalf("create hash: %v", err)
+	}
+	return hash
+}
+
+// recordingAuthRepo is an AuthRepository that also records which app password
+// was used, like the Postgres one does.
+type recordingAuthRepo struct {
+	used []uuid.UUID
+}
+
+func (r *recordingAuthRepo) FindByAddress(context.Context, string) (*port.MailboxAuth, error) {
+	return nil, nil
+}
+
+func (r *recordingAuthRepo) RecordAppPasswordUse(_ context.Context, id uuid.UUID) error {
+	r.used = append(r.used, id)
+	return nil
+}
+
+func TestVerifyCredential(t *testing.T) {
+	appID := uuid.New()
+	rec := &port.MailboxAuth{
+		ID:           uuid.New(),
+		PasswordHash: mustHash(t, "main-password-123"),
+		AppPasswords: []port.AppPasswordAuth{
+			{ID: appID, Hash: mustHash(t, "app-password-abc"), Scopes: []string{ScopeSMTP, ScopeIMAP}},
+			{ID: uuid.New(), Hash: mustHash(t, "imap-only-xyz"), Scopes: []string{ScopeIMAP}},
+		},
+	}
+	repo := &recordingAuthRepo{}
+
+	cases := []struct {
+		name     string
+		password string
+		scope    string
+		want     bool
+	}{
+		{"main password works for smtp", "main-password-123", ScopeSMTP, true},
+		{"main password works for imap", "main-password-123", ScopeIMAP, true},
+		{"app password works in a scope it holds", "app-password-abc", ScopeSMTP, true},
+		{"app password works for imap too", "app-password-abc", ScopeIMAP, true},
+		{"app password is refused outside its scopes", "app-password-abc", ScopePOP3, false},
+		{"an imap-only app password cannot send", "imap-only-xyz", ScopeSMTP, false},
+		{"an imap-only app password can read", "imap-only-xyz", ScopeIMAP, true},
+		{"wrong password fails", "nope", ScopeSMTP, false},
+		{"empty password fails", "", ScopeSMTP, false},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			got, err := verifyCredential(context.Background(), repo, rec, tc.password, tc.scope)
+			if err != nil {
+				t.Fatalf("unexpected error: %v", err)
+			}
+			if got != tc.want {
+				t.Fatalf("verifyCredential = %v, want %v", got, tc.want)
+			}
+		})
+	}
+
+	// Only the successful app password logins were recorded, and only that one
+	for _, id := range repo.used {
+		if id == rec.ID {
+			t.Fatalf("recorded the mailbox id as an app password use")
+		}
+	}
+	if len(repo.used) == 0 {
+		t.Fatalf("expected app password use to be recorded")
+	}
+}
+
+func TestVerifyCredentialMainPasswordDoesNotRecordAppUse(t *testing.T) {
+	rec := &port.MailboxAuth{
+		ID:           uuid.New(),
+		PasswordHash: mustHash(t, "main-password-123"),
+		AppPasswords: []port.AppPasswordAuth{{ID: uuid.New(), Hash: mustHash(t, "app-password-abc"), Scopes: []string{ScopeSMTP}}},
+	}
+	repo := &recordingAuthRepo{}
+
+	ok, err := verifyCredential(context.Background(), repo, rec, "main-password-123", ScopeSMTP)
+	if err != nil || !ok {
+		t.Fatalf("main password: ok=%v err=%v", ok, err)
+	}
+	if len(repo.used) != 0 {
+		t.Fatalf("a main password login must not touch app passwords, recorded %v", repo.used)
+	}
+}
+
+func TestVerifyCredentialMalformedAppHashIsSkipped(t *testing.T) {
+	rec := &port.MailboxAuth{
+		ID:           uuid.New(),
+		PasswordHash: mustHash(t, "main-password-123"),
+		AppPasswords: []port.AppPasswordAuth{
+			{ID: uuid.New(), Hash: "not-a-phc-string", Scopes: []string{ScopeSMTP}},
+			{ID: uuid.New(), Hash: mustHash(t, "app-password-abc"), Scopes: []string{ScopeSMTP}},
+		},
+	}
+
+	ok, err := verifyCredential(context.Background(), &recordingAuthRepo{}, rec, "app-password-abc", ScopeSMTP)
+	if err != nil || !ok {
+		t.Fatalf("a good app password must still work next to a broken one: ok=%v err=%v", ok, err)
+	}
+
+	ok, err = verifyCredential(context.Background(), &recordingAuthRepo{}, rec, "wrong", ScopeSMTP)
+	if err != nil || ok {
+		t.Fatalf("a broken app hash must not turn a wrong password into an error: ok=%v err=%v", ok, err)
+	}
+}
+
+func TestVerifyCredentialMalformedMainHashKeepsReportingTheError(t *testing.T) {
+	rec := &port.MailboxAuth{ID: uuid.New(), PasswordHash: "garbage"}
+
+	ok, err := verifyCredential(context.Background(), &recordingAuthRepo{}, rec, "anything", ScopeSMTP)
+	if ok {
+		t.Fatalf("must not authenticate against a malformed hash")
+	}
+	if err == nil {
+		t.Fatalf("a malformed main hash is a server-side fault and must surface as an error, as before")
+	}
+}
+
+func TestVerifyCredentialMalformedMainHashStillAllowsAnAppPassword(t *testing.T) {
+	rec := &port.MailboxAuth{
+		ID:           uuid.New(),
+		PasswordHash: "garbage",
+		AppPasswords: []port.AppPasswordAuth{{ID: uuid.New(), Hash: mustHash(t, "app-password-abc"), Scopes: []string{ScopeSMTP}}},
+	}
+
+	ok, err := verifyCredential(context.Background(), &recordingAuthRepo{}, rec, "app-password-abc", ScopeSMTP)
+	if err != nil || !ok {
+		t.Fatalf("ok=%v err=%v", ok, err)
+	}
+}
+
+// The three protocol entry points, wired the way the servers wire them: an app
+// password signs in where its scopes allow, and only there.
+
+func appPasswordMailbox(t *testing.T, scopes ...string) (port.MailboxAuth, string) {
+	t.Helper()
+	const secret = "app-password-from-the-webmail"
+	return port.MailboxAuth{
+		ID:           uuid.New(),
+		PasswordHash: mustHash(t, "the-real-mailbox-password"),
+		AppPasswords: []port.AppPasswordAuth{{ID: uuid.New(), Hash: mustHash(t, secret), Scopes: scopes}},
+	}, secret
+}
+
+func TestSubmissionAuthenticate_AcceptsAnAppPasswordWithTheSmtpScope(t *testing.T) {
+	rec, secret := appPasswordMailbox(t, ScopeSMTP)
+	uc := NewProcessOutboundEmailUseCase(&fakeAuthRepo{record: &rec}, nil, nil, nil)
+
+	got, err := uc.Authenticate(context.Background(), "user@example.test", secret)
+	if err != nil || got == nil || got.ID != rec.ID {
+		t.Fatalf("Authenticate = %+v, %v; want the mailbox", got, err)
+	}
+}
+
+func TestSubmissionAuthenticate_RefusesAnAppPasswordWithoutTheSmtpScope(t *testing.T) {
+	rec, secret := appPasswordMailbox(t, ScopeIMAP)
+	uc := NewProcessOutboundEmailUseCase(&fakeAuthRepo{record: &rec}, nil, nil, nil)
+
+	if _, err := uc.Authenticate(context.Background(), "user@example.test", secret); !errors.Is(err, ErrSubmissionAuthFailed) {
+		t.Fatalf("error = %v, want ErrSubmissionAuthFailed", err)
+	}
+}
+
+func TestImapLogin_AcceptsAnAppPasswordWithTheImapScope(t *testing.T) {
+	rec, secret := appPasswordMailbox(t, ScopeIMAP)
+	auth := &fakeAuthRepository{byAddress: map[string]port.MailboxAuth{"user@example.test": rec}}
+	uc := NewImapSessionUseCase(auth, nil, nil, nil, nil, nil, nil)
+
+	id, err := uc.Login(context.Background(), "user@example.test", secret)
+	if err != nil || id != rec.ID.String() {
+		t.Fatalf("Login = %q, %v; want %q", id, err, rec.ID)
+	}
+}
+
+func TestImapLogin_RefusesAnAppPasswordWithoutTheImapScope(t *testing.T) {
+	rec, secret := appPasswordMailbox(t, ScopeSMTP)
+	auth := &fakeAuthRepository{byAddress: map[string]port.MailboxAuth{"user@example.test": rec}}
+	uc := NewImapSessionUseCase(auth, nil, nil, nil, nil, nil, nil)
+
+	if _, err := uc.Login(context.Background(), "user@example.test", secret); !errors.Is(err, ErrAuthFailed) {
+		t.Fatalf("error = %v, want ErrAuthFailed", err)
+	}
+}
+
+func TestPop3Login_AcceptsAnAppPasswordWithThePop3Scope(t *testing.T) {
+	rec, secret := appPasswordMailbox(t, ScopePOP3)
+	auth := &fakeAuthRepository{byAddress: map[string]port.MailboxAuth{"user@example.test": rec}}
+	uc := NewPop3SessionUseCase(auth, nil, nil, nil, nil)
+
+	id, err := uc.Login(context.Background(), "user@example.test", secret)
+	if err != nil || id != rec.ID.String() {
+		t.Fatalf("Login = %q, %v; want %q", id, err, rec.ID)
+	}
+}
@@ -4,7 +4,6 @@ import (
 	"context"
 	"errors"

-	"github.com/alexedwards/argon2id"
 	"github.com/google/uuid"

 	"lambdamail/protocols/internal/application/port"
@@ -64,7 +63,7 @@ func (uc *ImapSessionUseCase) Login(ctx context.Context, address, password strin
 	if rec == nil {
 		return "", ErrAuthFailed
 	}
-	match, err := argon2id.ComparePasswordAndHash(password, rec.PasswordHash)
+	match, err := verifyCredential(ctx, uc.auth, rec, password, ScopeIMAP)
 	if err != nil {
 		return "", err
 	}
@@ -4,7 +4,6 @@ import (
 	"context"
 	"fmt"

-	"github.com/alexedwards/argon2id"
 	"github.com/google/uuid"

 	"lambdamail/protocols/internal/application/port"
@@ -42,7 +41,7 @@ func (uc *Pop3SessionUseCase) Login(ctx context.Context, username, password stri
 	if rec == nil {
 		return "", ErrAuthFailed
 	}
-	match, err := argon2id.ComparePasswordAndHash(password, rec.PasswordHash)
+	match, err := verifyCredential(ctx, uc.authRepo, rec, password, ScopePOP3)
 	if err != nil {
 		return "", fmt.Errorf("verify password hash: %w", err)
 	}
@@ -82,7 +82,7 @@ func (uc *ProcessOutboundEmailUseCase) Authenticate(ctx context.Context, address
 		return nil, ErrSubmissionAuthFailed
 	}

-	match, err := argon2id.ComparePasswordAndHash(password, rec.PasswordHash)
+	match, err := verifyCredential(ctx, uc.auth, rec, password, ScopeSMTP)
 	if err != nil || !match {
 		return nil, ErrSubmissionAuthFailed
 	}
@@ -0,0 +1,119 @@
+package e2e
+
+import (
+	"context"
+	"crypto/tls"
+	"net"
+	"testing"
+	"time"
+
+	"github.com/alexedwards/argon2id"
+	embeddedpostgres "github.com/fergusstrange/embedded-postgres"
+	"github.com/google/uuid"
+
+	appusecase "lambdamail/protocols/internal/application/usecase"
+	"lambdamail/protocols/internal/infrastructure/diskstorage"
+	"lambdamail/protocols/internal/infrastructure/dkim"
+	"lambdamail/protocols/internal/infrastructure/postgres"
+	smtppresentation "lambdamail/protocols/internal/presentation/smtp"
+
+	gosmtp "github.com/emersion/go-smtp"
+)
+
+// TestSubmissionAcceptsAppPasswords drives the real submission server over
+// STARTTLS. An app password is what a mail client uses on an account that has a
+// second factor, and it used to be refused everywhere because the protocols
+// only compared against the mailbox password.
+func TestSubmissionAcceptsAppPasswords(t *testing.T) {
+	if testing.Short() {
+		t.Skip("e2e test skipped in -short mode")
+	}
+	ctx := context.Background()
+
+	pg := embeddedpostgres.NewDatabase(embeddedpostgres.DefaultConfig().
+		Port(15445).
+		RuntimePath(t.TempDir()).
+		StartTimeout(120 * time.Second))
+	if err := pg.Start(); err != nil {
+		t.Fatalf("start embedded postgres: %v", err)
+	}
+	defer pg.Stop()
+
+	pool, err := postgres.NewPool(ctx, "postgres://postgres:postgres@localhost:15445/postgres?sslmode=disable")
+	if err != nil {
+		t.Fatalf("connect pool: %v", err)
+	}
+	defer pool.Close()
+	applyMigrations(t, ctx, pool)
+
+	const (
+		address      = "plataforma@apppass.test"
+		mainPassword = "the main mailbox password"
+		sendSecret   = "app password that may send"
+		readSecret   = "app password for reading only"
+	)
+
+	hashOf := func(secret string) string {
+		hash, err := argon2id.CreateHash(secret, argon2id.DefaultParams)
+		if err != nil {
+			t.Fatalf("hash: %v", err)
+		}
+		return hash
+	}
+
+	domainID, mailboxID := uuid.New(), uuid.New()
+	pool.Exec(ctx, `INSERT INTO domains (id, name, punycode_name) VALUES ($1, 'apppass.test', 'apppass.test')`, domainID)
+	pool.Exec(ctx, `INSERT INTO mailboxes (id, domain_id, local_part, email_address, password_hash) VALUES ($1, $2, 'plataforma', $3, $4)`,
+		mailboxID, domainID, address, hashOf(mainPassword))
+	// Default scopes: imap, pop3, smtp
+	pool.Exec(ctx, `INSERT INTO app_passwords (mailbox_id, label, password_hash) VALUES ($1, 'ciberlab', $2)`, mailboxID, hashOf(sendSecret))
+	pool.Exec(ctx, `INSERT INTO app_passwords (mailbox_id, label, password_hash, scopes) VALUES ($1, 'reader', $2, '{imap}')`, mailboxID, hashOf(readSecret))
+
+	blobs := diskstorage.NewLocalDiskBlobStorage(pool, t.TempDir())
+	submissionUC := appusecase.NewProcessOutboundEmailUseCase(postgres.NewAuthRepository(pool), postgres.NewOutboundRepository(pool), blobs, dkim.NewSigner(nil))
+
+	server := gosmtp.NewServer(smtppresentation.NewSubmissionBackend(submissionUC))
+	server.Domain = "mail.apppass.test"
+	server.AllowInsecureAuth = false
+	server.TLSConfig = &tls.Config{Certificates: []tls.Certificate{selfSignedTLSCert(t)}}
+
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("listen: %v", err)
+	}
+	defer ln.Close()
+	go server.Serve(ln)
+
+	login := func(password string) error {
+		client, err := gosmtp.DialStartTLS(ln.Addr().String(), &tls.Config{InsecureSkipVerify: true})
+		if err != nil {
+			t.Fatalf("dial: %v", err)
+		}
+		defer client.Close()
+		return client.Auth(plainAuth(address, password))
+	}
+
+	if err := login(mainPassword); err != nil {
+		t.Errorf("the mailbox password must keep working: %v", err)
+	}
+	if err := login(sendSecret); err != nil {
+		t.Errorf("an app password with the smtp scope must sign in: %v", err)
+	}
+	if err := login(readSecret); err == nil {
+		t.Error("an imap-only app password must not be able to submit mail")
+	}
+	if err := login("not a password"); err == nil {
+		t.Error("a wrong password must still be refused")
+	}
+
+	var stamped bool
+	pool.QueryRow(ctx, `SELECT last_used_at IS NOT NULL FROM app_passwords WHERE label = 'ciberlab'`).Scan(&stamped)
+	if !stamped {
+		t.Error("using an app password must stamp last_used_at")
+	}
+	var untouched bool
+	pool.QueryRow(ctx, `SELECT last_used_at IS NULL FROM app_passwords WHERE label = 'reader'`).Scan(&untouched)
+	if !untouched {
+		t.Error("a refused app password must not be stamped as used")
+	}
+}
@@ -38,5 +38,37 @@ func (r *AuthRepository) FindByAddress(ctx context.Context, address string) (*po
 		return nil, err
 	}
 	rec.ID = id
+
+	// The newest few only: each one costs an Argon2 comparison on a failed login,
+	// so the number considered is bounded.
+	rows, err := r.pool.Query(ctx, `
+		SELECT id, password_hash, scopes
+		FROM app_passwords
+		WHERE mailbox_id = $1
+		ORDER BY created_at DESC
+		LIMIT $2
+	`, id, port.MaxAppPasswordsChecked)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+
+	for rows.Next() {
+		var app port.AppPasswordAuth
+		if err := rows.Scan(&app.ID, &app.Hash, &app.Scopes); err != nil {
+			return nil, err
+		}
+		rec.AppPasswords = append(rec.AppPasswords, app)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+
 	return &rec, nil
 }
+
+// RecordAppPasswordUse stamps the moment an app password last signed a client in.
+func (r *AuthRepository) RecordAppPasswordUse(ctx context.Context, id uuid.UUID) error {
+	_, err := r.pool.Exec(ctx, `UPDATE app_passwords SET last_used_at = NOW() WHERE id = $1`, id)
+	return err
+}
@@ -5,6 +5,9 @@ import (
 	"testing"

 	"github.com/google/uuid"
+	"github.com/jackc/pgx/v5/pgconn"
+
+	"lambdamail/protocols/internal/application/port"
 )

 func TestAuthRepository_FindByAddress_ReturnsHashForActiveMailbox(t *testing.T) {
@@ -56,3 +59,121 @@ func TestAuthRepository_FindByAddress_ReturnsNilForUnknownAddress(t *testing.T)
 		t.Errorf("rec = %+v, want nil", rec)
 	}
 }
+
+// seedAuthMailbox creates a throwaway domain and mailbox and returns the mailbox id
+// and address. Cleanup removes the domain, which cascades to the rest.
+func seedAuthMailbox(t *testing.T, pool interface {
+	Exec(context.Context, string, ...any) (pgconn.CommandTag, error)
+}) (uuid.UUID, string) {
+	t.Helper()
+	ctx := context.Background()
+
+	domainID := uuid.New()
+	domainName := "authrepo-app-" + domainID.String() + ".invalid"
+	if _, err := pool.Exec(ctx, `INSERT INTO domains (id, name, punycode_name) VALUES ($1, $2, $3)`, domainID, domainName, domainName); err != nil {
+		t.Fatalf("seed domain: %v", err)
+	}
+	t.Cleanup(func() { pool.Exec(ctx, `DELETE FROM domains WHERE id = $1`, domainID) })
+
+	mailboxID := uuid.New()
+	address := "user@" + domainName
+	if _, err := pool.Exec(ctx, `INSERT INTO mailboxes (id, domain_id, local_part, email_address, password_hash) VALUES ($1, $2, 'user', $3, 'main-hash')`,
+		mailboxID, domainID, address); err != nil {
+		t.Fatalf("seed mailbox: %v", err)
+	}
+	return mailboxID, address
+}
+
+func TestAuthRepository_FindByAddress_LoadsAppPasswordsWithTheirScopes(t *testing.T) {
+	pool := testPool(t)
+	defer pool.Close()
+	ctx := context.Background()
+
+	mailboxID, address := seedAuthMailbox(t, pool)
+
+	if _, err := pool.Exec(ctx, `INSERT INTO app_passwords (mailbox_id, label, password_hash) VALUES ($1, 'phone', 'hash-default-scopes')`, mailboxID); err != nil {
+		t.Fatalf("seed app password: %v", err)
+	}
+	if _, err := pool.Exec(ctx, `INSERT INTO app_passwords (mailbox_id, label, password_hash, scopes) VALUES ($1, 'reader', 'hash-imap-only', '{imap}')`, mailboxID); err != nil {
+		t.Fatalf("seed app password: %v", err)
+	}
+
+	rec, err := NewAuthRepository(pool).FindByAddress(ctx, address)
+	if err != nil || rec == nil {
+		t.Fatalf("FindByAddress: rec=%v err=%v", rec, err)
+	}
+	if len(rec.AppPasswords) != 2 {
+		t.Fatalf("AppPasswords = %d, want 2", len(rec.AppPasswords))
+	}
+
+	byHash := map[string][]string{}
+	for _, app := range rec.AppPasswords {
+		byHash[app.Hash] = app.Scopes
+	}
+	if got := byHash["hash-default-scopes"]; len(got) != 3 {
+		t.Errorf("default scopes = %v, want imap, pop3 and smtp", got)
+	}
+	if got := byHash["hash-imap-only"]; len(got) != 1 || got[0] != "imap" {
+		t.Errorf("imap-only scopes = %v, want [imap]", got)
+	}
+}
+
+func TestAuthRepository_FindByAddress_AMailboxWithoutAppPasswordsStillWorks(t *testing.T) {
+	pool := testPool(t)
+	defer pool.Close()
+
+	_, address := seedAuthMailbox(t, pool)
+
+	rec, err := NewAuthRepository(pool).FindByAddress(context.Background(), address)
+	if err != nil || rec == nil {
+		t.Fatalf("FindByAddress: rec=%v err=%v", rec, err)
+	}
+	if len(rec.AppPasswords) != 0 {
+		t.Errorf("AppPasswords = %v, want none", rec.AppPasswords)
+	}
+}
+
+func TestAuthRepository_FindByAddress_ReadsOnlyTheNewestAppPasswords(t *testing.T) {
+	pool := testPool(t)
+	defer pool.Close()
+	ctx := context.Background()
+
+	mailboxID, address := seedAuthMailbox(t, pool)
+
+	for i := 0; i < port.MaxAppPasswordsChecked+5; i++ {
+		if _, err := pool.Exec(ctx, `INSERT INTO app_passwords (mailbox_id, label, password_hash, created_at) VALUES ($1, $2, 'h', NOW() - make_interval(mins => $3))`,
+			mailboxID, "label", i); err != nil {
+			t.Fatalf("seed app password: %v", err)
+		}
+	}
+
+	rec, err := NewAuthRepository(pool).FindByAddress(ctx, address)
+	if err != nil || rec == nil {
+		t.Fatalf("FindByAddress: rec=%v err=%v", rec, err)
+	}
+	if len(rec.AppPasswords) != port.MaxAppPasswordsChecked {
+		t.Errorf("AppPasswords = %d, want the cap of %d", len(rec.AppPasswords), port.MaxAppPasswordsChecked)
+	}
+}
+
+func TestAuthRepository_RecordAppPasswordUse_StampsLastUsedAt(t *testing.T) {
+	pool := testPool(t)
+	defer pool.Close()
+	ctx := context.Background()
+
+	mailboxID, _ := seedAuthMailbox(t, pool)
+
+	var appID uuid.UUID
+	if err := pool.QueryRow(ctx, `INSERT INTO app_passwords (mailbox_id, label, password_hash) VALUES ($1, 'phone', 'h') RETURNING id`, mailboxID).Scan(&appID); err != nil {
+		t.Fatalf("seed app password: %v", err)
+	}
+
+	if err := NewAuthRepository(pool).RecordAppPasswordUse(ctx, appID); err != nil {
+		t.Fatalf("RecordAppPasswordUse: %v", err)
+	}
+
+	var stamped bool
+	if err := pool.QueryRow(ctx, `SELECT last_used_at IS NOT NULL FROM app_passwords WHERE id = $1`, appID).Scan(&stamped); err != nil || !stamped {
+		t.Fatalf("last_used_at not set: stamped=%v err=%v", stamped, err)
+	}
+}