I've done a handful of side-by-side migrations or deployments.

I think you already identified the generally best approach IMHO:

    >  Conceptually the simplest would be to have a auth cookie that is 
valid in both, it could be set to only be created in one and honoured in 
the other.

However I recommend it with one caveat -- I would approach this 
functionality as if it were it's own authentication micro-service.  It can 
live in one of the two processes, it doesn't need a third, but I would 
structure the UX, tests and development as if it were totally independent 
-- so the cookie value would just contain login state the core account info 
needed for auth and permissions.  If either process needs to store other 
data in a cookie, use another cookie.

Reading Pyramid cookies in Flask is pretty simple, Pyramid sessions just 
automate loading webob cookies with defaults

* https://github.com/Pylons/pyramid/blob/master/src/pyramid/session.py
* https://github.com/Pylons/webob/blob/master/src/webob/cookies.py


In terms of Pyramid versions, if you need Python2 support - 1.10 is your 
only option.  Otherwise, just pay attention to the deprecations on Pyramid2 
and you should be able to transition from 1.10 to 2 very easily if you 
don't want to run the pre-release.  Michael Merickel is the expert on this, 
but I think he and his team have done a great job in planning the 2.0 
changes by offering a lot of "forward compatibility' options in 1.10 to 
prepare us for switching to 2.0.  I could be wrong, but I think almost 
every one of the 2.0 changes can be elected in 1.10.  The only difference I 
know of is the drastic change to authentication/authorization (which may be 
worth using the pre-release). 


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