This question has been answered by kjforsyth. See the first response.
It sounds like a cache issue. If you clear the site cache in the Manager after updating the fields, do they appear correctly in the web Context? If not, try manually deleting the files in the core/cache directory after saving the user (just for diagnostic purposes).
In theory, the user cache is refreshed when you save a user, but that may happen before the extra fields are saved.
Did you try the things I suggested to diagnose the problem?
Did you try the things I suggested to diagnose the problem?
Also, when you update the custom fields in the Manager, do they change in the MODX database
(views in PhpMyAdmin from cPanel)?