I Let ChatGPT Sign Into My Web Accounts for Me, and It Was More Trouble Than It’s Worth

AI agents are becoming more capable over time, and the latest ability rolled out to ChatGPT Work (that's the agentic bit of ChatGPT) is being able to sign into websites—and in theory, taking even more of your workload off you. The official examples of how you might want to use this include setting up utilities for a new apartment, organizing an appointment with a doctor, and canceling tickets for a rescheduled trip. "If it's something you’d normally have to open a browser and click through yourself, try asking ChatGPT Work to do it," says the sales pitch.

I'm all for saving time on admin, but handing over my login credentials to ChatGPT feels like a bold step. Can I trust ChatGPT to keep my details safe and secure? And what are the chances of it going haywire once it's in my accounts? In the interests of finding out, I let it log into some of my less important accounts to see what it could do.

This feature is rolling out now in the web and mobile apps for those on ChatGPT Plus, Pro, and Business accounts.

Will ChatGPT store your usernames and passwords?

According to the ChatGPT release notes for August 25, 2026, "ChatGPT cannot see your username or password, and they are never seen by the model or used in model training. ChatGPT does not store your username or passwords." So how does it work if your usernames or passwords are never stored? The most basic option here is to simply sign in through ChatGPT when prompted by a site or app (and clear any two-factor authentication challenges at the same time), and then have the AI stay logged in for future tasks.

The more advanced version, which is where you save a more significant chunk of time, is to give ChatGPT permission to interface with a third-party password manager. ChatGPT doesn't specify a list of supported password managers, but as far as I can tell, this is just for mobile: Any password manager on your phone can pop up when ChatGPT needs it and supply the relevant credentials.

Browser data can be managed inside ChatGPT. Credit: Lifehacker

Underpinning all this is an actual browser, built into ChatGPT, that it can access and operate itself. Your accounts will see it as a new sign in (like they would if you signed in from a new device), and some websites and apps will let you mark ChatGPT as a "trusted" operator that can log in again in the future,

You can control the data held by this browser: From ChatGPT on the web, click your profile icon (bottom left), then Settings > Cloud browser. You can delete stored cookies from here, for example, which will effectively kick the AI out of any sites it has access to. As per ChatGPT support: "You stay in control of which websites ChatGPT Work can access, and it will always ask for confirmation before consequential actions, such as completing a reservation or payment." Exactly how it can tell when it's about to do something consequential, however, isn't clear.

Here's what happened when I gave ChatGPT some tasks to do for me

If you want to make use of this inside ChatGPT on the web, click Work at the top of the screen to switch to agent mode, then tell the AI what you want to do: Something like "sign into my eBay account and tell me how my auctions are doing" or "sign into my accounting app and submit these invoices."

I gave the eBay one a go first—the process proved to be incredibly slow for whatever reason, and I could've signed in multiple times in the normal way by the time ChatGPT got around to gaining access. There are also problems where the ChatGPT conversation tends to obfuscate what's going on: It asked for a verification code, and I didn't know where to check for it.

You can, at any point, switch to the ChatGPT browser itself, which I eventually did to get through the verification code stage (it was sent over text). The AI was then able to correctly tell me what the current auction prices were on the items I was bidding on, after initially stumbling through several wrong pages—there's a thumbnail of the live browser in the corner of the screen, so you can see what's happening.

The built-in web browser can be opened or hidden. Credit: Lifehacker

Next up, I tasked ChatGPT with getting into my Airbnb account and finding some great spots close to Santa Cruz, Calif., within a certain price range. Again, I had to switch to the actual browser view to sign in (I was told the Airbnb site wasn't cooperating), but once I had given the AI access, it worked smoothly enough, looking up properties and giving me a rundown of prices.

At the moment, the sign-in flows are just too finicky. Sites seem suspicious of the AI browser, everything is really slow, and you run into complications with verification codes, passkeys, and the like. You'll often have to manually sign in as you would anyway in order to get ChatGPT up and running on a site.

ChatGPT can retrieve information okay, but tends to take its time. Credit: Lifehacker

Once that's done, though, everything works reasonably impressively, as long as you're giving commands that are fairly easy to interpret and carry out. ChatGPT on Airbnb seems competent with dates and locations, but I'm not sure it could filter through places based on the view or the general vibe of the decor.

Perhaps most importantly, I still don't trust the AI to do these jobs better than I can, even if it can (eventually) do it more quickly. I want to see for myself what an Airbnb looks like, or who's bidding on an eBay auction, or what the available time slots are for an appointment to get my car serviced—if I left it to ChatGPT, I'd be too worried about it missing something (I have the same reservations about letting friends and family do things for me as well, but that's another issue).

In my testing, ChatGPT didn't fail in any of the tasks I gave it once it had gained access to these sites, or give me any inaccurate answers, but that would always be at the back of my mind if I switched over to this completely. For now, I'm going to stick to these online admin tasks myself.