On the eve of the new millennium, everyone — except Dilbert — is making New Year's plans. While assuring everyone that the company is prepared for Y2K, Dilbert discovers that the computer mainframe's main processor isn't Y2K-compatible and all the company's systems will crash if it isn't fixed. Dilbert is rewarded for discovering this by being assigned to fix it, and he discovers that the system's original programmer was Wally. But have years of drudgework dulled his brain too much to be able to tackle this crucial task?

Dilbert loses "the knack" for technology when he gets management DNA from accidentally drinking from the Boss's cup. His resulting mis-steps send the world back to the Dark Ages.

Dilbert is tasked with naming a product that hasn't even been designed yet, and the stress (brought on by a recurring nightmare) makes Dilbert think he's turning into a chicken.

Dilbert and Wally become majority shareholders of their company after Dogbert manipulates the stock market.

Dilbert is forced to be a charity coordinator for the "Associated Way" charity drive.

Dilbert and Alice must work together to stop a rival team led by the legendary "Lena" from stealing their ideas and presenting them to the Boss as her own.

The Gruntmaster 6000 prototype is put to the test by an evil masked test engineer named Bob Bastard.

Dilbert discovers that the office is inhabited by a race of former employees who have been "downsized" (literally shrunken down to size after they've been laid off) after finding all of his belongings used, the dry-erase markers disappearing, and X-rated websites on his computer.

The pre-production—non-lab-tested—Gruntmaster 6000 is scheduled to be tested by a Texan family.

Dilbert, Alice, Wally, Dogbert, and the Pointy-Haired Boss take a business trip to Elbonia. Alice and Dilbert attempt to free the Elbonian people (Alice adopts an Elbonian baby while Dilbert introduces the workers to human rights) while Wally becomes a prophet.

The repetitive passing-on of the same cold strain in Dilbert's office causes it to mutate and turns the coworkers into monsters. Rather than eliminate the virus, the company decides to start fresh by moving everyone to a new office, which Dilbert is tasked with designing.

Dilbert thinks there are too many time-wasting holidays; Dogbert concurrently convinces Congress to abandon all holidays in favor of a National Dogbert Day.

Dilbert is fired from his job when he is suspected of being a spy for a rival company (which was a rumor cooked up by Dogbert's online newsletter) and gets hired at a company that actually treats their workers like people.