Although the decade is not yet over, the 2000s have brought sweeping changes at Redwood, with advances in technology altering the classroom experience and major modernization of the school buildings.

The first unforgettable memory of the 2000s was the terrorist attacks in New York on September 11, 2001. The flag in front of Redwood stood at half-mast as students huddled around car radios and teachers suspended lesson plans for the day.
An assembly was held in lieu of a previously scheduled Spirit Rally to commemorate the tragedy and unify the Redwood community in light of this unprecedented attack. Afterwards, several students transformed the Spirit Ball into a memorial to those who died.
“I felt it was important to pull together as a student body and talk about how important it is… to become one community,” Principal Nancy Neu said in the Sept. 2001 issue of the Bark.. 
Over the next few years, technology became a larger part of student life as cell phones and iPods replaced pagers and CD-players.
In Oct. 2001, Computer Programming students created Nibbles, which soon evolved into a school-wide phenomenon.
“We must face the fact that Nibbles is taking over the school,” said Clay Shaw in an Oct. 2001 Bark  article.
According to Applied Technology department chair Dave Goldsmith, the game entertained 120-140 students per day. 
However, in Fall of 2007, a server change deleted Nibbles from school computers and Goldsmith decided not to reinstall it, bringing the six-year legacy to a close. 
Aside from Nibbles, another computer craze exploded through cyberspace.  MySpace and Facebook, websites that allow members to set up personal accounts and communicate with friends and strangers, became an integral part of student’s social lives.
According to a 2006 Bark  survey, 84% of females and 62% of males said they had MySpace accounts that they checked regularly.
Though MySpace helped students procrastinate, as a whole, standards at Redwood continued to increase.  This year, 25 honors and AP courses are offered at Redwood, while many colleges had the lowest admit rate in 27 years.
Attempted senior pranks in the 2000s have typically gone awry.
The 2006 senior prank left a scar of Redwood’s reputation when five seniors bought 32 chickens and released them in the world languages hallway.
The Marin Humane Society removed the chickens and filed felony charges that were later dropped against the students, who were not allowed to attend their graduation ceremony.
Less publicized, but still chaotic, was the senior prank in 2004 when the doors to the school were chained shut just before lunch, leaving everyone trapped inside. Students, thinking there might be a gunman trying to keep everyone inside, panicked and some even climbed out the windows of classrooms and poured out the back doors to the counseling office.
Another dark moment in Redwood’s past was in Spring 2007, when the boys’ varsity lacrosse team was stripped of their MCAL title. Following Redwood’s victory in the championship game against Marin Catholic, two Redwood players were deemed ineligible by MCAL rules due to incomplete paperwork regarding their transfer from Marin Catholic to Redwood.  The team was forced to forfeit their near-perfect season, leading Redwood students to question Marin Catholic’s motives.
Back at Redwood, however, construction was a constant presence.  Though the $33,088,500 modernization project was estimated to be finished by November 2005, a new lunch area is currently being built, as well as a new pool and practice gym.