After the Snowden revelations, interest in encrypted end-to-end communication has skyrocketed, even amongst ordinary users. However, today we still do not have widespread deployment of OpenPGP. Post-email messaging protocols such as OpenWhisper has around a million users. Poor usability has led users in sensitive situations to misunderstand or give up on encryption tools, putting them at risk. Why isn’t everyone encrypting their communications by now? This panel brings together speakers from software, protocol, and usability projects to reflect on current challenges to Encrypting All The Things, discuss what has worked and what hasn’t in FLOSS projects developing secure tools, and possibly develop strategies for the future.