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@null if its AWS-based check the dynamodb module
Is silverstripe going to update their webpack settings to support react 16?
I've come across the multi-server issue before, it's a scary one to troubleshoot 😄
I'm just assuming you've checked the former two :>
Anyway, in my experience your issue is generally caused by either something eating your sessions, the session timeout value is way too low, or there's a multi server setup that's hitting a different server (and sessions aren't shared).
albeit an older one than that