The SecureDrop anonymous whistleblowing platform has become the journalism industry standard for communicating with anonymous sources and accepting high security leaks. The system was co-created by the late Aaron Swartz and first announced at HOPE four years ago. Each SecureDrop instance is physically hosted inside a news organization, and sources communicate with journalists by accessing a web application available over a Tor onion service. In the past two years, adoption has increased to include most major new organizations, including The Associated Press, USA Today, and The Wall Street Journal. This talk will cover the challenges SecureDrop administrators, journalists, and sources are facing, how SecureDrop has been scaled to more organizations, and progress in developing new tools for journalists to work with leaked documents, including a Qubes OS-based workstation. In the Trump era - during which the Department of Justice has issued a crackdown on whistleblowing in response to the current epidemic of leaks from the White House - secure communication tools like SecureDrop are more important than ever before.