There is increasingly strong evidence that taxation can contribute to expanded government responsiveness and accountability. However, such positive connections are not guaranteed. Rather, they are shaped by the political and economic context and specific policies adopted by governments and civil society actors. Without an environment that enables tax bargaining, there is a risk that taxation will amount to little more than forceful extraction. We consider how such enabling environments may be fostered through two mixed methods case studies of tax transparency and taxpayer engagement in Sierra Leone and Ghana. We highlight two key sets of findings. First, tax transparency is only meaningful if it is accessible and easily understood by taxpayers and relates to their everyday experiences and priorities. In particular, we find that taxpayers do not just want basic information about tax obligations or aggregate revenue collected, but information about how much revenue should have been collected and how revenues were spent. At the same time, taxpayers do not want information to be shared with them through a one-way form of communication, but rather want to have spaces for dialogue and interaction with tax and government officials, including through public meetings and radio call-in programmes. Second, strategies to encourage taxpayer engagement are more likely to be effective where forums for engagement are perceived by taxpayers to be safe, secure, and sincere means through which to engage with government officials. This has been most successful where governments have visibly demonstrated responsiveness to citizen concerns, even on a small scale, while partnering with civil society to foster trust, dialogue and expanded knowledge. These findings have significant implications for how governments design taxpayer education and engagement programmes and how civil society actors and development partners can support more equitable and accountable tax systems. Our findings provide concrete lessons for how governments can ensure that information shared with taxpayers is meaningful and accessible. Moreover, we show that civil society actors can play important roles as translators of tax information, enablers of public forums and dialogues around tax issues, and trainers of taxpayers, supporting greater tax literacy and sustained citizen engagement.