Bots are estimated to account for well over half of all web traffic, yet they remain an understudied topic in HCI. In this paper we present the findings of an analysis of 2284 submissions across three discussion groups dedicated to the request, creation and discussion of bots on Reddit. We set out to examine the qualities and functionalities of bots and the practical and social challenges surrounding their creation and use. Our findings highlight the prevalence of misunderstandings around the capabilities of bots, misalignments in discourse between novices who request and more expert members who create them, and the prevalence of requests that are deemed to be inappropriate for the Reddit community. In discussing our findings, we suggest future directions for the design and development of tools that support more carefully guided and reflective approaches to bot development for novices, and tools to support exploring the consequences of contextually inappropriate bot ideas.