A client of mine has run her business on the same CRM for fifteen years. When we sat down to connect it to ChatGPT Work, it was missing from the plugin directory. Fine, second option: connect by API key. We looked it up and found that her plan, the original model she signed up on all those years ago, had no API key at all. She had to migrate to the vendor's newest platform version, and once she did, the agent connected in seconds.
That hour taught her more about her tech stack than any audit. The tools your business depends on are either doors the agent can open or walls it has to climb, and you find out which by connecting everything and watching what resists.
Where Plugins Live and How They Work
In the new ChatGPT app, click Plugins in the left sidebar. You will find the directory: Gmail, Google Drive, Google Calendar, Notion, Slack, HubSpot, Dropbox, Canva, Zoom, GitHub, Cloudflare, the Outlook family for Microsoft users, and around eighty more behind the See all link. There are far more today than there were three months ago, and the direction is one-way: software that wants to survive is becoming agent-connectable.
Each plugin signs in with its own account approval, the same way you approve any app. Once connected, you call a tool by typing @ and its name in a request, like @gmail.
Connect everything relevant in one sitting. If you connect half your apps and then ask the agent to audit your business, it audits half a business. Ask "are we undercharging based on what we deliver?" without your meeting recorder connected, and it answers from contracts alone: no client conversations, no scope creep visible, no emotion in the room. The answer will be generic, and generic answers are what owners complain about right before I find out the agent was working blind.
The Connections That Earn Their Place
| Connection | Why it matters |
|---|---|
| Gmail + Google Calendar + Google Drive | The core three. Google's infrastructure is very agent-friendly, and if you are a Gmail business, you start with an advantage. Email is how the agent acts on your behalf; Drive is where your business's memory lives. |
| Outlook, Teams | The Microsoft equivalents, all present in the directory. Connect whichever family you actually live in. |
| Notion | Very future-forward and agent-friendly. No CRM? The agent can run a simple one in Notion, plus content calendars and SOPs, without you maintaining any of it. |
| GitHub | Just get it. Free account. It will be critical once you or your team start building anything, because it is where agents keep versioned, recoverable work. |
| Cloudflare | Trust me on this one. Free to start, and the moment you take websites or custom tools seriously, you will need it. GitHub plus Cloudflare is the must-have pair. |
| Dropbox | If your company runs on it, connect it. I spoke with a construction company carrying twenty years of project files in Dropbox; humans were spending hours a week filing and retrieving. That is the lowest-hanging fruit an agent can take over, once the structure is organized for agents and not just humans. |
| Zoom / Fireflies | Your call recordings are the richest context your business produces: pricing signals, scope creep, client emotions, onboarding gaps. A business that records conversations hands its agent all of that. A business that does not is at a serious disadvantage to one that does. |
| HubSpot | If you are entrenched in HubSpot, stay. Agents work well inside it, and ripping out a working CRM is rarely the move for established businesses. |
| Stripe | Very agent-friendly. I run mine through the API key rather than the plugin. "Send this client an invoice for the deal we closed today" becomes one sentence instead of ten clicks. |
| Canva | Optional, and I say this with love to the Canva loyalists: the app's built-in image generation now covers most thumbnails, posters, and social designs. Connect it if your workflows live there. |
Do Not Trust the Connection. Confirm It.
A connected plugin can still be read-only, and read-only means the agent can see your emails but never draft or send one. So after you connect everything, run this before your first real task:
Paste into Work mode
Please confirm the plugins that you have read and write access to. List each connected tool and state whether you can only read from it or also create, edit, and send. Flag any connection where you expect to be blocked from doing real work.
Mine came back confirming read and write on Gmail, Google Calendar, Google Drive, Notion, GitHub, Slack, Zoom, Canva, and Fireflies. Now I know what it can act on, instead of hoping.
When the Plugin Is Too Small for the Job
Plugins expose a fixed menu of permissions, and sooner or later the agent will tell you it cannot do something through one. My Cloudflare plugin does plenty, and I still keep a Cloudflare API token with broader permissions because I want more than the plugin's menu.
When you hit the wall, do what I do: have an attitude of curiosity. Ask why. Ask "are you sure?" Then ask this:
When the agent says it can't
How could you do that? Help me. I am not technical and not a coder. Use the browser and computer use to walk me through exactly what I need to get you the access you need, step by step, and tell me when to click.
That prompt has walked my clients through getting API keys they did not know existed, from tools they had used for a decade.
The Software Verdict Nobody Wants
Sometimes the connection exercise delivers a verdict about your stack. My own website ran on Kajabi for years, and Kajabi has no plugin here. Invoicing through it meant the agent clicking around a human interface with computer use: slow, token-hungry, fragile. I stopped fighting it, rebuilt the entire site on GitHub and Cloudflare, and now the agent updates, deploys, and invoices in seconds through connections built for it. (If your business is heavily dependent on a tool that only connects well to a different AI, that is worth weighing too; Kajabi, for instance, shipped its integration for Claude first.)
The test is simple. If a core tool blocks the agent at every step, forces computer use for basic operations, and has no API on your plan, you are paying for that tool twice: once in subscription, once in everything your agent cannot do. Software will adapt as this becomes the norm. The question is whether you wait for your vendor or move to tools that are already agent-ready.
Common Questions
Which plugin should I connect first? Whichever tool holds your business's context: email, Drive, and your meeting recorder. Then connect the rest in the same sitting.
Is it safe to connect my email? Set the posture first: the agent drafts, you send. The setup tutorial covers permissions in plain language.
My tool isn't in the directory. Now what? Connect by API key. If your plan has no API, that is your sign the software is aging out of the agent era.
Do I need GitHub and Cloudflare if I'm not technical? Yes, free accounts on both, created with your main business email. You will not use them directly; your agent will.
What does connecting everything cost? Connections are free. The work the agent does across them is metered, covered in the pricing guide.
Bottom Line
Your agent's ceiling is your stack's openness. Connect everything, confirm read and write, and let what resists tell you what to replace.