Looking for an AI That Actually Has Context on You?
At some point most people using AI tools hit the same wall: the model is smart, but it doesn't...
At some point most people using AI tools hit the same wall: the model is smart, but it doesn't know anything about you. Every answer is built for a generic average person, so you spend the first half of every conversation supplying context before you get anything useful. If you're searching for an AI that actually has context on you and your work, here's the honest landscape — and why the answer might not be a different AI.
Why doesn't AI have context on you by default?
Because the models are built to be general, and being general is the opposite of knowing you specifically. A language model is trained on the world's text, not your life. Out of the box it has no idea what you do, what you're working on, or how you like things — and at the start of each conversation, it knows only what's in front of it right now.
So "the AI doesn't have context on me" isn't a flaw in a particular tool. It's the default state of every general AI. The tools that feel like they know you are the ones with something extra layered on top — and that layer is exactly where the differences (and the limits) live.
Do any AI tools actually have context on you?
They have features that try. The major tools all added some form of it:
- Memory (ChatGPT, Claude, Gemini) — accumulates facts and preferences from your conversations over time. Helps, but it's reactive (starts empty, fills in slowly) and stays inside that one tool.
- Custom instructions / preferences — a field where you write standing context. Better, because you control it — but you maintain it by hand, and it's per-tool.
- Connectors — let an AI reach into your Gmail, Drive, or Notion. Useful for retrieval, but giving a tool access to a source isn't the same as it understanding who you are.
Each helps. None fully solves it, and all of them share one trait: the context lives inside that specific tool. Which leads to the trap.
Why switching AIs won't fix it
Because the wall isn't the AI — it's where the context lives. If you leave ChatGPT for Claude because Claude "gets you" better, you set up Claude's memory and preferences, and it does get better. Then you try Cursor for coding, or a new tool launches, and you're cold again — re-explaining yourself from scratch, rebuilding context you already built elsewhere.
You can do this forever. Every tool you adopt starts not knowing you, and every tool's context stays trapped in that tool. The search for "an AI that has context on me" turns into a loop of re-onboarding yourself to each new AI. The problem was never which model you picked.
The actual fix: context that lives outside the tool
What gives any AI context on you is a layer that holds your context and serves it to whatever tool you're using. Instead of each AI building its own partial, siloed picture, you maintain one structured context — who you are, how you work, what you're doing now — extracted from your real sources, owned by you, and delivered to any AI through MCP.
That flips the model. The AI doesn't need to slowly learn you; it receives your context at the start of the session. Switch tools, try the new thing, use three AIs at once — they all draw on the same accurate context, because the context isn't trapped in any of them. You stop shopping for an AI that knows you and start owning the context that makes every AI know you.
So if you're looking for an AI that has context on you, the more useful question is: where does your context live? Put it in a layer that travels, and the tool becomes a choice you can change freely — without starting over each time.
→ Why this happens: Why Doesn't AI Remember Me?
→ What that context layer is: What Is Personal Context for AI?
→ Give every AI context on you — Unabyss →
