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Then you have an outdated, pirated, translated or edited game version. I don't know what to tell you - the code is extremely simple and literally cannot bug out in this instance.

Outdated:  Make sure you've downloaded the latest version. When you open your game, the first screen will have a version number on it. Make sure it matches the version number listed in the files above.

Pirated:  If you got the game from anywhere other than Patreon, Subscribestar or Itch then it's not official and will very likely contain bugs, malicious code and errors not present in the official versions.

Translated:  If you are using a translated version, or patch, then your version is not official and any bugs need to be reported to the person who made the translation.

Edited:  If you, or someone with access to your computer/game/saves has edited anything in the game then there's a very good chance the entire game will break. There's no way to fix this except by reverting back to a save prior to the editing or starting again.

Other than the above reasons, there's no way for the event you're talking about to break. CK is a hard-coded visual novel and makes no realtime changes, so if one person is getting a code-related bug then everyone will. It's not case by case.

The only other thing I can think of is that you're at the wrong stage of the quest. You don't get Samantha's key the first time you meet Jackie (when she's in her Zero Suit cosplay and tied up) - you get it later on, when you revisit her and she's randomly either "Jackie?" or "Jackie".