: Protagonist knows things which the reader doesn't know/story starts in the middle. How do I tell them? when I say "reader", in the context of my particular scenario, I actually mean

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Never ever tell unless it is absolutely necessary. Nobody wants to read a chapter that's talking about history or backstory.
Instead, try to show your reader. For example:
If for a thousand years there has been a war going on between dragons and humans, then let the reader know this information by having people talk about a battle plan, how one has failed a long time ago, open up to a fight scene, have someone watch the battle from a distance, etc.
Never start a book saying:

For a thousand years there has been war with dragons and humans, it started when blah blah blah.

No one wants to read that.

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From a storytelling perspective it's fine to start in the middle - many novels and films do it successfully. Video games are a bit different because of the degree of interactivity, but it’s still possible if you’re careful in your execution.
I love the Portal games, and while the sense of disorientation and lack of initial knowledge is key to the atmosphere of those games, there’s no reason your approach can’t work in a similar setting. It will probably just have a slightly different feel if Kate and David already know a lot about their surrounds.
Assuming your audience is likely to be Portal fans, they will already be familiar with sentient technology. To me, David mentioning his admin rights or referring to previous activities shouldn’t be a problem - I would quickly realise that David knows what’s happening and his tone and reaction to me would show that he is friendly.
However, I cannot know everything that Kate knows if I haven’t been given that information, so you need to give me access to Kate’s prior knowledge. There are plenty of ways to do this that are common in games - journal entries, computer records, books, maps, a friendly robot, a voiceover. You would need to consider pacing - as with novels, an infodump can be boring and difficult to absorb, so you’ll need to figure out what information to provide automatically, what the player can request as and when they’re ready for it, and what to drip-feed throughout the game.
Alternatively, you could find a reason why Kate is having to figure out things she should already know, e.g. she was injured or drugged and can’t remember anything, she’s never used a portal gun before, or been to this section of the building.
In addition to knowledge, there is also the physical aspect to consider. If you read a book written in the first person, and it says ‘I fire the gun,’ then you as a reader assume you know how to fire that type of gun. Maybe the author gives some backstory or leaves you to imagine it, but either way, you’ve been told you do it, so you know you can.
However, at the start of a video game the player doesn’t even know what they can interact with, let alone how to use the items. At some point, they need to learn the controls and gameplay logic (usually through a tutorial unless the gameplay is incredibly simple). In many games, the player starts at the beginning of the character’s journey because it makes logical sense that the player figures out the gameplay while the character figures out their surroundings: the player and character grow in step with each other. Starting in the middle of the story, you’ll need to be sensitive with your tutorial to allow the player to pick up gameplay and potentially large amounts of knowledge alongside each other.

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