Provided that both the client subscribed and the server publishing the message retain the connection, is Redis guaranteed to always deliver the published message to the subscribed client eventually, even under situations where the client and/or server are massively stressed? Or should I plan for the possibility that Redis might ocasionally drop messages as things get "hot"?
Redis does absolutely not provide any guaranteed delivery for the publish-and-subscribe traffic. This mechanism is only based on sockets and event loops, there is no queue involved (even in memory). If a subscriber is not listening while a publication occurs, the event will be lost for this subscriber.
It is possible to implement some guaranteed delivery mechanisms on top of Redis, but not with the publish-and-subscribe API. The list data type in Redis can be used as a queue, and as the the foundation of more advanced queuing systems, but it does not provide multicast capabilities (so no publish-and-subscribe).
AFAIK, there is no obvious way to easily implement publish-and-subscribe and guaranteed delivery at the same time with Redis.