After the family went to bed and I started checking it out, I figured it out.
It installs "per user", I have it running as a non-privileged account since it auto-logs in.
Apparently it needs privileged permissions to install or update.
If you update(install) it as the non priv acccount and just enter admin creds when prompted, it will install the updated version under the admin account.
I elevated the non-priv account to admin and it successfully updated. This resolved the issue.
I suspect that this is the reason it has not auto-updated also even though I have it set to. (Although it is weird that it reports "up to date" when you check and the update tasks all report "successful).
Is it possible to update file/folder/registry permissions and run this as a non-priv account?