Flask Session will not Persist
Problem was that I had the key static in my init which caused it to work in dev but in production in the .wsgi it was still dynmaic, I have changed this and all seems to be working now.
I have recently deployed my first Flask application (first web application ever actually), one problem I am running into and haven't had luck tracking down is related to sessions. 
What I am doing is when the user logs in I set session['user'] = user_id and what is happening is I occasionally get a key error when making a request involving that session key. If I try to make the request again the session key is there and the request works fine. I have done research and set the app.config['SERVER_NAME'] to my domain and made sure the secret_key was static, it was dynamic before. 
This does not happen when on my local development server so I am a bit stumped at this point.