Drawing flow charts

So I’ve started drawing some flows with more detail. First out is the login flow. We needed this because we started talking about what would happen if one User would need access to more than one Agency. With the decision based on Agencies Count, I got some UX design included in the architecture. We do not want to show a list of only one Agency, that’s typical bad UX.
The AuthenticationMiddleware intercepts all API calls, and checks if Authentication is required, and if so, it validates the Bearer token, and sets the claims to the Context.

The UserProvisioningMiddleware intercepts all API calls and, if we have Claims in the Context, makes sure the current users local Identifier is set to the Context, for use in calls to the database, for permission control.

One thing that I’m having a bit of trouble handling is that the development of the application is faster than my architectural work. This means there’s part of the application that has accidental architecture. The accidental architecture isn’t necessarily bad, but it lacks the comparison to the naive architecture, i.e. not scientifically proven.
I’m not sure if I should use the accidental architecture as the base line, but I guess I could do that.