The third question I get is a complaint: “I have to explain who I am every single time.” That’s true, and it’s also exactly the difference you pay for with most of these tools: whether the assistant knows you the moment you open a new chat.
This is part 3 of 6. Part 1 covered free versus paid, part 2 covered search. This part is about four ways an assistant can get to know you, and which of them are free.
Four ways to be known
The first is memory: the assistant remembers things from earlier conversations on its own. ChatGPT, Claude and Grok have it, Gemini has it if you use a personal account and keep the activity setting on, and Perplexity has it and lets you switch it off separately from your search history. At Claude it’s on by default on every personal plan, free included; searching old chats is paid only.
The second is a standing instruction: a text you write once that goes along with every chat. “I write about wine, keep it plain, no dashes.” ChatGPT gives you 1,500 characters for that on free and 5,000 on paid. Claude, Gemini and Grok have it too. At Perplexity it only exists inside a project, up to 8,000 characters, and whether you can create such a project for free the help page doesn’t say.
The third is a project: a folder with its own instructions and its own files, so the assistant already knows your brand brief or your case file for everything you ask inside it. ChatGPT allows five files per project on free, twenty-five or forty on paid. Claude allows five projects on free, unlimited on paid. Perplexity recently started calling its spaces projects too, and Gemini has Gems, small assistant variants with a fixed brief.
The fourth is a connection to your own stuff: your mail, your files, your calendar, or a tool of your own through MCP, an open standard for hooking an assistant up to your own files or apps. This is where the paywall is sharpest. At Perplexity the Gmail, Drive and Dropbox connections are Pro and Max only. At Claude the standard connections are free and you may add one custom connection for free. At ChatGPT it depends on the app and your plan. At Grok the documentation says connections are for all users. Gemini connects to Gmail and Drive through its Workspace app, and that only works while you keep your activity saved.
The table
Checked on 6 September 2026, from the makers’ own help pages.
| Memory | Standing instruction | Project | Connections | |
|---|---|---|---|---|
| ChatGPT | Yes, limited on free; on or off under Settings, Personalization | 1,500 characters free, 5,000 paid | 5 files free, 25 or 40 paid; building your own GPTs isn’t possible on any personal plan | Per app, depending on your plan |
| Claude | Yes, on by default on every personal plan; searching old chats paid only | Yes, per account | 5 free, unlimited paid; skills on every plan | Standard connections free, one custom MCP connection free |
| Gemini | Yes, given a personal account, age 18, activity saving on | Yes, “saved info” | Gems, on the same conditions | Gmail and Drive through the Workspace app; the proactive variant isn’t available in the EEA, the EU plus Norway, Iceland and Liechtenstein |
| Grok | Yes, “memory across chats” | Yes | Not found as a separate feature | “Available to all users” according to the documentation |
| Perplexity | Yes, can be switched off separately from search history; the self-improving memory is Max only | Yes, up to 8,000 characters per project | Yes | Gmail, Drive, Dropbox on Pro and Max only |
Where the pages contradict each other
This is the part that took me longest, and it’s worth knowing before you subscribe. At two of the five, the pricing page and the help page say different things.
ChatGPT: the pricing page puts projects at Plus and up, the help page says they’re available on every plan, free included, with five files. And the pricing page says you can build your own GPTs on Plus, while the help page says creating and publishing GPTs isn’t possible on any personal account, Plus and Pro included.
Claude: one help page says free users can create five projects, and three paragraphs further down that project instructions are for paid plans only. The pricing page puts projects on every plan.
I couldn’t resolve either by asking. What I can say: don’t subscribe on the strength of one page. Try the feature on free and you’ll know within a minute.
What I see myself
Claude is where I’ve set up the most: projects with my brand brief in them, skills for recurring work, connections to the tools I publish with, and memory. How I learned it is less exciting than it sounds: mostly watching a lot of tutorials and following the instructions from the Claude team. The Claude Code team and the Design team often share valuable tips and tricks too.
In Gemini I made a Gem and switched saved info on, and it pulls in things from my Gmail and Drive without being asked. That’s useful, and it’s also the subject of the next part.
Free ChatGPT: no memory that I notice. Perplexity and Grok I haven’t set up for this.
Caveat: what it knows about you goes somewhere
Everything in this part is one movement: you give more of yourself, the assistant gets more useful. Your name, your job, your files, your mail. The better it knows you, the less you want to switch, because none of that setup comes with you. That’s the lock-in that came up in part 1, and here it’s concrete.
The second point is that “free” at Gemini doesn’t hang on a plan but on a setting: memory, Gems and the Gmail connection only work while you keep your activity saved. And saved activity, according to Google’s own privacy page, is also used to train its models. The price of a personal assistant at Google isn’t an amount. Part 4 is about that.
What to do tomorrow
Write one standing instruction of three sentences and put it in the assistant you use now: who you are, what you use it for, and one thing it should never do. That takes two minutes and saves you every chat after it.
Frequently asked questions
Do I have to pay to make an AI remember me?
No. Memory is in the free tier at all five, a standing instruction at four; at Perplexity it lives inside a project, and whether that’s free isn’t confirmed. Paying buys you more room, more files per project, and the connections to your mail and files.
Why does ChatGPT forget what I said in another chat?
Because memory is limited on free and can be on or off. Look under Settings, Personalization, Memory. A temporary chat never creates memories anyway.
Sources: memory in ChatGPT, custom instructions in ChatGPT, projects in ChatGPT, memory in Claude, projects in Claude, custom connectors in Claude, memory in Gemini, Gemini Apps Privacy Hub, Grok, Grok connectors, memory in Perplexity, projects in Perplexity. Checked 6 September 2026.