From 1999 to 2006, Dolan served with the Marines in two deployments during the Iraq War where he worked as a data network specialist.
[2] In 2003, Dolan served with III Marine Expeditionary Force[citation needed] during the initial Iraq War.
In his second deployment, which was from September 2004 to March 2005,[2] Dolan served with 4th Civil Affairs Group in Fallujah,[citation needed] which was one of the centers of the conflict at that time.
[3] In 2012, as a side project to his IT job, Dolan helped develop the open source SecureDrop, initially known as DeadDrop.
[7][8][9] In 2015, Dolan moved to San Diego, California, to work as head of security at Classy, an American software company and an online fundraising platform designed for nonprofit organizations, a position he held at the time of his death.