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In The Matrix films, when someone wants to connect into the Matrix, it requires three things:

  • To find somewhere to link in the real work (they can't just connect from anywhere, they must find someplace to connect the ship)
  • An Operator to guide those who are connected (every time someone wanted to log off the Matrix, they called the Operator to find an exit)
  • Someone to insert the plug and remove it

At some point, Cypher needed those three things to log into the Matrix and talk to Smith at the restaurant scene. How did Cypher connect without an Operator?

Even without an Operator, if someone showed up while Cypher was connected and looked at the screen, wouldn't they know Cypher was talking to an agent?

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Per my answer here on Scifi:SE, According to the Wachowskis, Neo interrupts Cypher writing a script (some kind of automated operator) that will enable him to enter and leave the Matrix without a human operator present.

WachowskiBros: Cypher, at the beginning of this scene, is setting up an automated system to allow him to go meet with Agent Smith.

As to how he got the jack into his head, we're left to assume that he simply reached behind himself.

  • I guess the main question is: how did he remove the plug, as by convention you are not in control of your physical body when inside the Matrix. – Juha Untinen Jun 5 '18 at 13:00
  • @JuhaUntinen He probably wouldn't need to physically remove the cable, he would be electrically disconnected and would then wake up. I believe the operator is there to get you out of trouble, which Cypher wouldn't need because he was colluding with the Agents. – James Hollis Jun 5 '18 at 14:50
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I always assumed he didn't really need to jack in -- after all, he's the one who stated that

All I see now is blonde, brunette, redhead.

so I just assumed he was just sitting at his terminal, appearing to be busy as usual.

(I realize this is a very late addition, but a different angle nonetheless.)

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