Very. The larger the site, the harder it becomes.
My co-worker Nick Craver just blogged about the multi-year journey to enable HTTPS at StackOverflow.com and all our sub-properties (spoiler alert: there is still more work to do!) It is probably the best detailed description of the process. If your boss ever asks you why HTTPS can't be enabled in just a few hours, this is a good resource.
https://nickcraver.com/blog/2017/05/22/https-on-stack-overflow/
Leave a comment