Flag Day means a software change that is not backward-compatible, especially in a network system where upgrade is scheduled early and everybody must deploy upgrade at (before) the date, or the system will stop working. It came into use when a change was made to the definition of the ASCII character set during the development of Multics. The change was scheduled for Flag Day (a U.S. holiday, https://en.wikipedia.org/wiki/Flag_Day_(United_States) ), June 14, 1966.