I think you are on the right track, wp_cache_delete was what finally helped me get an auto-signup with auto-login plugin working… I have this from there:
wp_cache_delete($current_user->ID, 'users');
wp_cache_delete($current_user->user_login, 'userlogins');
Then see what roles you get after that with:
$current_user = wp_get_current_user();
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