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Slack is the market leader in persistent group messaging, supporting millions of users daily, for hours each day. Slack's core messaging experience is connection-oriented, maintaining long-lived, stateful sessions to enable a low-latency, highly present user experience. Scaling a connection-oriented service presents challenges that differ from those of a typical, request-based web service. In this talk we'll explore the evolution to date of Slack's technical underpinnings, which have evolved from supporting teams of hundreds, to thousands, to hundreds of thousands of users. Since Slack is not done scaling, we'll also discuss some possible future directions.