[BUG] Claude tries multiple times to create pop-up larger than Safari Maximum popup size

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

I have a Safari pop-up for an extensions settings in a modal window. I asked Claude to add features to the pop-up and to add more buttons, and then buttons begin to get cut off so I request the popup window be made larger. Claude will continue multiple times and waste a lot of tokens and hours trying to make the window larger and the size of the pop-up modal will never change.

The sizing is enforced by Safari and from what I know, the maximum height is 600 pixels. However, instead of downsizing buttons or icons in the Settings modal, Claude will try to extend the window each time by 50 pixels to make things fit, though the max is 600px Claude will keep trying and with mine it was trying up to 850px.

Claude is then going around in circles, and the problem is never solved until the user mentions something like:

"Is there a maximum size for these popups? Should you maybe try and resize the content in the window?"

Once Claude begins to resize the icons and everything else, then the content fits, and the window doesn't need to be extended. Claude needs to be trained on the maximum size of these popups it can create.

What Should Happen?

This shouldn't be allowed to happen, Claude needs to be trained to know those values so in the future, he can do things quicker. If modal windows are only allowed to be a maximum of 600px high, then that needs to be in the model.

Error Messages/Logs

There are no error messages while this is happening, and Claude has no clue why it's not working.

Steps to Reproduce

I guess you would create a Safari extension and have a window and fill it with content. Fill it with a square that's 595 pixels. Then begin typing lines underneath, and you will see them go off the edge of the window. This proves that there is a maximum height for that window. Then ask Claude to adjust the window because you can't see your text at the bottom of your 595 pixel square. Explain how the text is cut off, and you need to be able to see it. Claude will then begin to slowly add 50px increments or 100px increments and we'll keep telling you to quit and restart Safari. And we'll tell you it should work now. And Claude will also blame things on the cache version, etc. It has nothing to do with that. It's a Safari maximum pop-up window size which is 600 pixels in height.

Claude Model

Opus

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

2.0.69

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

NA