diff --git a/app/core/src/main/java/com/fsck/k9/controller/MessagingController.java b/app/core/src/main/java/com/fsck/k9/controller/MessagingController.java
index 8b4b081dc..d988dd496 100644
--- a/app/core/src/main/java/com/fsck/k9/controller/MessagingController.java
+++ b/app/core/src/main/java/com/fsck/k9/controller/MessagingController.java
@@ -671,9 +671,21 @@ public class MessagingController {
     }
 
     public void handleAuthenticationFailure(Account account, boolean incoming) {
+        if (account.shouldMigrateToOAuth()) {
+            migrateAccountToOAuth(account);
+        }
+
         notificationController.showAuthenticationErrorNotification(account, incoming);
     }
 
+    private void migrateAccountToOAuth(Account account) {
+        account.setIncomingServerSettings(account.getIncomingServerSettings().newAuthenticationType(AuthType.XOAUTH2));
+        account.setOutgoingServerSettings(account.getOutgoingServerSettings().newAuthenticationType(AuthType.XOAUTH2));
+        account.setShouldMigrateToOAuth(false);
+
+        preferences.saveAccount(account);
+    }
+
     public void handleException(Account account, Exception exception) {
         if (exception instanceof AuthenticationFailedException) {
             handleAuthenticationFailure(account, true);
diff --git a/mail/common/src/main/java/com/fsck/k9/mail/ServerSettings.kt b/mail/common/src/main/java/com/fsck/k9/mail/ServerSettings.kt
index 492f83164..ca365fb4d 100644
--- a/mail/common/src/main/java/com/fsck/k9/mail/ServerSettings.kt
+++ b/mail/common/src/main/java/com/fsck/k9/mail/ServerSettings.kt
@@ -26,4 +26,8 @@ data class ServerSettings @JvmOverloads constructor(
     fun newPassword(newPassword: String?): ServerSettings {
         return this.copy(password = newPassword)
     }
+
+    fun newAuthenticationType(authType: AuthType): ServerSettings {
+        return this.copy(authenticationType = authType)
+    }
 }