Air date: 4/21/99

Dilbert loses "the knack" for technology when he drinks from the Boss's cup by mistake and gets management DNA. His following goof-ups send the world back to the Dark Ages.

Y2K

Air date: 5/3/99

It's the eve of the new millenium, and everyone is making new years plans, except for Dilbert that is. While everyone celebrates the new age, they also get caught up in Y2K hysteria, and while assuring everyone that the company is prepared, Dilbert discovers that the computer mainframe's main processor isn't Y2K-compatible, and all of the company's systems will crash if it isn't fixed. Dilbert is assigned the job of correcting the crucial mistake, which can only be fixed by the system's original programmer, Wally.

Charity

Air date: 5/10/99

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

Holiday

Air date: 5/17/99

Dilbert is annoyed at the amount of holidays because he believes it to be a waste of time. Dogbert concurrently convinces Congress to abandon all holidays in favor of a National Dogbert Day.

The Infomercial

Air date: 5/24/99

The pre-production Gruntmaster 6000 is scheduled to be tested by a Texan family, despite not being tested in the lab first.

Tower of Babel

Air date: 5/22/99

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