Milo Pressman is an independent technological contractor, brought in to CTU to work on a key card that was left by now dead agent Richard Walsh. The key card contains information regarding the assassination plot against Senator David Palmer.

When first introduced, Milo joins CTU to break into the keycard, but before he can do so, Jack Bauer is forced to switch the key card with a fake one for villain Ira Gaines. Milo then figures out that he has been working with a different key card, and he suspects that Jack may have switched it when he came to his desk. After Jamey Farrell is revealed as a mole, agent Nina Myers has Milo research Gaines’ identity, putting Milo in charge of all Jamey’s projects. Although Milo has narrowed the missing Teri Bauer's location down, it is still too large of an area to pinpoint the exact spot.

Agent Tony Almeida finds an encrypted email on Jamey's computer and has Milo decode it. Milo then looks to find the remaining shooters. At CTU, Milo briefs Jack about the three possible shooters he uncovered. One of them is Alexis, Victor Drazen's son who had been trained in Belgrade’s special forces. Milo forwards the photos of the suspected assassins to the Secret Service, and Agent Pierce shows them to the assembled Palmer campaign team. When Jack becomes suspicious of another mole being in CTU, he asks Milo to watch the servers for any classified information being leaked. Milo's last act for the day was notifying Jack that Robert Ellis (the connection between Bauer and Palmer to Operation Nightfall) was found murdered in New Orleans.