I Allowed ChatGPT to Automatically Log Me Into My Web Accounts and It Caused Me More Trouble Than It Was Worth.
Artificial intelligence is becoming increasingly sophisticated, and the latest feature added to ChatGPT Work (the agent portion of ChatGPT) is the ability to log into websites , which, in theory, makes your job even easier. Official use cases include connecting utilities to a new apartment, arranging a doctor’s appointment, and canceling tickets for a rescheduled trip. “If you usually have to open a browser and click links yourself, try asking ChatGPT Work to do it for you,” the promotional text says.
I’m all for saving time on administration, but handing over my login credentials to ChatGPT seems like a bold move. Can I trust ChatGPT to keep my data safe? And what’s the likelihood that the system will crash if it gains access to my accounts? To find out, I allowed it to log into some of my less important accounts to see what it could do.
This feature is already rolling out to the web and mobile apps for ChatGPT Plus, Pro, and Business account users.
Will ChatGPT store your usernames and passwords?
According to the ChatGPT release notes from August 25, 2026, “ChatGPT doesn’t see your username or password, and they are never visible to the model or used in the model training process. ChatGPT does not store your usernames or passwords.” So how does this work if your usernames or passwords are never stored? The simplest option is to simply log in through ChatGPT when a website or app prompts you to do so (while simultaneously resetting all two-factor authentication requests), and then allow the AI to remain logged in for future tasks.
A more advanced option that can save you a lot of time is to grant ChatGPT permission to interact with a third-party password manager. ChatGPT doesn’t list supported password managers, but as far as I understand, this only applies to mobile devices: any password manager on your phone can appear when ChatGPT requires it and provide the necessary credentials.
At the core of all this is ChatGPT’s built-in browser, which the system can access and manage independently. Your accounts will treat this as a new login (as if you were logging in from a new device), and some websites and apps will allow you to mark ChatGPT as a “trusted” operator, allowing you to log in again in the future.
You can control the data stored in this browser: in the web version of ChatGPT, click your profile icon (bottom left), then “Settings” > “Cloud Browser.” Here, you can, for example, delete stored cookies, which will effectively log the AI out of all websites it has access to. As ChatGPT support states, “You retain control over which websites ChatGPT Work can access, and it will always ask for confirmation before important actions, such as completing a booking or payment.” However, how exactly it determines when it’s about to perform something important is unclear.
Here’s what happened when I gave ChatGPT some tasks.
If you want to use this feature in the web version of ChatGPT, click “Work” at the top of the screen to switch to agent mode, then tell the AI what you want to do: for example, “log in to my eBay account and tell me how my auctions are going” or “log in to my accounting app and send these invoices.”
I tried eBay first—the process was incredibly slow for some reason, and I had to log in regularly several times before ChatGPT finally allowed access. Another problem is that the ChatGPT conversation obscures what’s going on: it asked for a verification code, and I didn’t know where to find it.
At any time, you can switch to the ChatGPT browser itself, which is what I eventually did to complete the code verification step (it was sent via text message). After that, the AI was able to correctly determine the current auction prices for the items I bid on, after several attempts at incorrectly selecting pages failed. There’s a thumbnail of the running browser in the corner of the screen, so you can see what’s going on.
Next, I instructed ChatGPT to log into my Airbnb account and find some great places to stay near Santa Cruz, California, within a certain price range. Again, I had to switch to a regular browser to log in (I was told the Airbnb website was down), but once I granted the AI access, everything worked quite well: it searched for properties and provided me with a list of prices.
Currently, the authorization process is too inconvenient. Websites are wary of an AI-powered browser, everything works very slowly, and there are difficulties with confirmation codes, passwords, and the like. Often, you have to log in manually, as before, to launch ChatGPT on the website.
However, after that, everything works quite impressively, as long as you issue commands that are easy enough to understand and execute. ChatGPT on Airbnb seems to handle dates and locations well, but I’m not sure it can filter places by view or overall ambiance.
Perhaps most importantly, I still don’t trust AI to handle these tasks better than I can myself, even if it can (eventually) do them faster. I want to see for myself what Airbnb looks like, who’s bidding on eBay, or what time slots are available for car maintenance—if I trusted ChatGPT to do that, I’d be too worried about it missing something (I have similar concerns about letting friends and family do things for me, but that’s a different issue).
During my tests, ChatGPT didn’t fail any of the tasks assigned to it after accessing these sites and didn’t provide any inaccurate answers, but I’ll always keep this in mind if I fully transition to this system. For now, I’ll be performing these online administration tasks myself.