fix(smtp): outlook smtp not authenticating when enterprise or educational accounts

app-thunderbird/src/debug/kotlin/net/thunderbird/android/auth/TbOAuthConfigurationFactory.kt

@@ -65,6 +65,7 @@ class TbOAuthConfigurationFactory : OAuthConfigurationFactory {
         ) to OAuthConfiguration(
             clientId = "e6f8716e-299d-4ed9-bbf3-453f192f44e5",
             scopes = listOf(
+                "profile",
                 "openid",
                 "email",
                 "https://outlook.office.com/IMAP.AccessAsUser.All",

legacy/common/src/main/java/com/fsck/k9/backends/RealOAuth2TokenProvider.kt

@@ -21,13 +21,33 @@ class RealOAuth2TokenProvider(
     private val authService = AuthorizationService(context)
     private var requestFreshToken = false
 
-    override val primaryEmail: String?
+    override val usernames: Set<String>
         get() {
-            return parseAuthState()
-                .parsedIdToken
-                ?.additionalClaims
-                ?.get("email")
-                ?.toString()
+            val idTokenClaims = parseAuthState().parsedIdToken?.additionalClaims.orEmpty()
+            return buildSet {
+                // https://learn.microsoft.com/en-us/entra/identity-platform/id-token-claims-reference#payload-claims
+                // https://docs.azure.cn/en-us/entra/identity-platform/optional-claims-reference
+                // requires profile scope
+                idTokenClaims["preferred_username"]?.let { add(it.toString()) }
+                // requires email scope
+                idTokenClaims["email"]?.let { add(it.toString()) }
+                // only present for v1.0 tokens
+                idTokenClaims["unique_name"]?.let { add(it.toString()) }
+                // requires profile scope
+                idTokenClaims["upn"]?.let { add(it.toString()) }
+                idTokenClaims["verified_primary_email"]?.let { verifiedPrimaryEmail ->
+                    when (verifiedPrimaryEmail) {
+                        is List<*> -> addAll(verifiedPrimaryEmail.map { it.toString() })
+                        else -> add(verifiedPrimaryEmail.toString())
+                    }
+                }
+                idTokenClaims["verified_secondary_email"]?.let { verifiedSecondaryEmail ->
+                    when (verifiedSecondaryEmail) {
+                        is List<*> -> addAll(verifiedSecondaryEmail.map { it.toString() })
+                        else -> add(verifiedSecondaryEmail.toString())
+                    }
+                }
+            }
         }
 
     @Suppress("TooGenericExceptionCaught")

mail/common/src/main/java/com/fsck/k9/mail/oauth/OAuth2TokenProvider.kt

@@ -11,15 +11,14 @@ interface OAuth2TokenProvider {
     }
 
     /**
-     * Fetch the primary email found in the id_token additional claims,
-     * if it is available.
+     * A set of usernames fetched from the `id_token`.
      *
      * > Some providers, like Microsoft, require this as they need the primary account email to be the username,
-     * not the email the user entered
+     * > not the email the user entered for SMTP authentication.
      *
-     * @return the primary email present in the id_token, otherwise null.
+     * @throws AuthenticationFailedException If no AuthState is available.
      */
-    val primaryEmail: String?
+    val usernames: Set<String>
         @Throws(AuthenticationFailedException::class)
         get
 

mail/protocols/imap/src/test/java/com/fsck/k9/mail/store/imap/ImapServerSettingsValidatorTest.kt

@@ -351,7 +351,7 @@ class ImapServerSettingsValidatorTest {
     }
 }
 
-class FakeOAuth2TokenProvider(override val primaryEmail: String? = null) : OAuth2TokenProvider {
+class FakeOAuth2TokenProvider(override val usernames: Set<String> = emptySet()) : OAuth2TokenProvider {
     override fun getToken(timeoutMillis: Long): String {
         return AUTHORIZATION_TOKEN
     }

mail/protocols/imap/src/test/java/com/fsck/k9/mail/store/imap/RealImapConnectionTest.kt

@@ -1273,7 +1273,7 @@ class RealImapConnectionTest {
     }
 }
 
-class TestTokenProvider(override val primaryEmail: String? = null) : OAuth2TokenProvider {
+class TestTokenProvider(override val usernames: Set<String> = emptySet()) : OAuth2TokenProvider {
     private var invalidationCount = 0
 
     override fun getToken(timeoutMillis: Long): String {

mail/protocols/smtp/src/main/java/com/fsck/k9/mail/transport/smtp/SmtpTransport.kt

@@ -155,6 +155,7 @@ class SmtpTransport(
                 AuthType.NONE -> {
                     // The outgoing server is configured to not use any authentication. So do nothing.
                 }
+
                 AuthType.PLAIN -> {
                     // try saslAuthPlain first, because it supports UTF-8 explicitly
                     if (authPlainSupported) {
@@ -165,13 +166,15 @@ class SmtpTransport(
                         throw MissingCapabilityException("AUTH PLAIN")
                     }
                 }
+
                 AuthType.CRAM_MD5 -> {
                     if (authCramMD5Supported) {
                         saslAuthCramMD5()
                     } else {
                         throw MissingCapabilityException("AUTH CRAM-MD5")
                     }
                 }
+
                 AuthType.XOAUTH2 -> {
                     if (oauthTokenProvider == null) {
                         throw MessagingException("No OAuth2TokenProvider available.")
@@ -183,13 +186,15 @@ class SmtpTransport(
                         throw MissingCapabilityException("AUTH OAUTHBEARER")
                     }
                 }
+
                 AuthType.EXTERNAL -> {
                     if (authExternalSupported) {
                         saslAuthExternal()
                     } else {
                         throw MissingCapabilityException("AUTH EXTERNAL")
                     }
                 }
+
                 else -> {
                     throw MessagingException("Unhandled authentication method found in server settings (bug).")
                 }
@@ -551,26 +556,68 @@ class SmtpTransport(
     private fun saslOAuth(method: OAuthMethod) {
         Log.d("saslOAuth() called with: method = $method")
         retryOAuthWithNewToken = true
+        checkNotNull(oauthTokenProvider) { "No OAuth2TokenProvider available." }
 
-        val primaryEmail = oauthTokenProvider?.primaryEmail
-        val primaryUsername = primaryEmail ?: username
+        val users = buildSet {
+            // add the given username to the list of users
+            add(username)
+            // add all the usernames we can fetch from the id_token to be used in case
+            // the given username fails to authenticate.
+            addAll(oauthTokenProvider.usernames)
+        }.toMutableSet()
 
-        try {
-            attempOAuth(method, primaryUsername)
-        } catch (negativeResponse: NegativeSmtpReplyException) {
-            Log.w(negativeResponse, "saslOAuth: failed to authenticate.")
-            if (negativeResponse.replyCode != SMTP_AUTHENTICATION_FAILURE_ERROR_CODE) {
-                throw negativeResponse
-            }
+        val negativeResponses = authenticateUsers(users, method)
 
-            oauthTokenProvider!!.invalidateToken()
+        if (negativeResponses.isNotEmpty()) {
+            Log.w("failed to authenticate with all discovered users.")
+            val (user, negativeResponse) = negativeResponses[username]?.let { username to it }
+                ?: negativeResponses.entries.first().toPair()
+
+            logger.log("invalidating current token")
+            oauthTokenProvider.invalidateToken()
 
             if (!retryOAuthWithNewToken) {
                 handlePermanentOAuthFailure(method, negativeResponse)
             } else {
-                handleTemporaryOAuthFailure(method, primaryUsername, negativeResponse)
+                handleTemporaryOAuthFailure(
+                    method = method,
+                    username = user,
+                    negativeResponseFromOldToken = negativeResponse,
+                )
+            }
+        }
+    }
+
+    private fun authenticateUsers(
+        users: MutableSet<String>,
+        method: OAuthMethod,
+    ): MutableMap<String, NegativeSmtpReplyException> {
+        val negativeResponses = mutableMapOf<String, NegativeSmtpReplyException>()
+        val sensitiveLog = "*sensitive*"
+        logger.log("users = ${users.takeIf { K9MailLib.isDebugSensitive() } ?: "[${users.size} emails found]"}")
+
+        val iterator = users.iterator()
+        while (iterator.hasNext()) {
+            val user = iterator.next()
+            try {
+                logger.log(
+                    "trying to authenticate with user '${
+                        user.takeIf { K9MailLib.isDebugSensitive() } ?: sensitiveLog
+                    }'",
+                )
+                attempOAuth(method, user)
+                negativeResponses.clear()
+                break
+            } catch (negativeResponse: NegativeSmtpReplyException) {
+                Log.w(negativeResponse, "saslOAuth: failed to authenticate.")
+                if (negativeResponse.replyCode != SMTP_AUTHENTICATION_FAILURE_ERROR_CODE) {
+                    throw negativeResponse
+                }
+                iterator.remove()
+                negativeResponses += user to negativeResponse
             }
         }
+        return negativeResponses
     }
 
     private fun handlePermanentOAuthFailure(

mail/protocols/smtp/src/test/java/com/fsck/k9/mail/transport/smtp/SmtpServerSettingsValidatorTest.kt

@@ -124,7 +124,7 @@ class SmtpServerSettingsValidatorTest {
             trustedSocketFactory = trustedSocketFactory,
             oAuth2TokenProviderFactory = { authStateStorage ->
                 assertThat(authStateStorage.getAuthorizationState()).isEqualTo(AUTHORIZATION_STATE)
-                FakeOAuth2TokenProvider(primaryEmail = expectedUser)
+                FakeOAuth2TokenProvider(usernames = setOf(expectedUser))
             },
         )
 
@@ -136,7 +136,14 @@ class SmtpServerSettingsValidatorTest {
             output("250-AUTH PLAIN LOGIN XOAUTH2")
             output("250 HELP")
 
-            val ouathBearer = "user=${expectedUser}\u0001auth=Bearer ${AUTHORIZATION_TOKEN}\u0001\u0001"
+            var ouathBearer = "user=${USERNAME}\u0001auth=Bearer ${AUTHORIZATION_TOKEN}\u0001\u0001"
+                .encodeUtf8()
+                .base64()
+
+            expect("AUTH XOAUTH2 $ouathBearer")
+            output("535 5.7.3 Authentication unsuccessful")
+
+            ouathBearer = "user=${expectedUser}\u0001auth=Bearer ${AUTHORIZATION_TOKEN}\u0001\u0001"
                 .encodeUtf8()
                 .base64()
 
@@ -397,7 +404,7 @@ class SmtpServerSettingsValidatorTest {
     }
 }
 
-class FakeOAuth2TokenProvider(override val primaryEmail: String? = null) : OAuth2TokenProvider {
+class FakeOAuth2TokenProvider(override val usernames: Set<String> = emptySet()) : OAuth2TokenProvider {
     override fun getToken(timeoutMillis: Long): String {
         return AUTHORIZATION_TOKEN
     }