What I'd imagine happening is this:
1. You're connecting on http, not https so...
2. The key isn't in the session, which will (correctly) raise an issue.

If you're doing https, I think you need to put Pyramid behind something 
(i'm not sure if pserve can handle https or not).

I run nginx on my macbook and proxypass back to pserve

so it looks like this:

    pyramid serves my project on port 5000
    nginx proxypass localhost http traffic (port 80) to port 5000
    nginx proxypass localhost https traffic (port 443) to port 5000

i believe the default nginx settings will convey the https status of the 
connection to wsgi (waitress/pserve)  

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