Hi Will,
I recall chatting to you on Reddit regarding the csrftoken on Sakai and login issues - while this may not be directly linked to your issue, I thought I should share.
We also use /direct and used to log users in using a POST to /direct/session. While this creates a session, it does not create a csrf token, allowing the user to access /direct as well as /portal tools, but doesn't allow users to submit forms on pages due to the missing csrf token.
As a workaround, we're currently using a POST to /portal/xlogin to log in users (which does create a token), and they have access to /direct - I opened a ticket on JIRA, but I'm relatively new to contributing to the project and from what I've seen on JIRA tickets can take a while.
Loading up a community master build and I'll continue poking around and.