Is it possible to attach the Web Inspector to the Captive Portal Assistant Dropdown?

I don’t know of any special magic to enable this. If the standard approach doesn’t work (and I presume you tried that before posting), my recommendation is that you file an enhancement request for a way to enable this.

Please post your bug number, just for the record.

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—
Quinn “The Eskimo!”
Apple Developer Relations, Developer Technical Support, Core OS/Hardware

let myEmail = "eskimo" + "1" + "@apple.com"

I made a few stabs at the bundle identifier, but I don't know if I used the wrong one or if it doesn't work.

So, yes I tried, but I don't know if I tried well...

I made a few stabs at the bundle identifier, but I don't know if I used the wrong one or if it doesn't work.

I’m confused as to why the bundle identifier would matter. My understanding is that web views that you can ‘connect to’ show up in the Develop menu in Safari. If the web sheets now showing up there, how else might you connect to it?

Share and Enjoy
—
Quinn “The Eskimo!”
Apple Developer Relations, Developer Technical Support, Core OS/Hardware

let myEmail = "eskimo" + "1" + "@apple.com"

Sorry, I was looking at the docs here https://developer.apple.com/library/content/documentation/AppleApplications/Conceptual/Safari_Developer_Guide/GettingStarted/GettingStarted.html

Since it didn't show up under the menu, this was my best guess to enable it. Reading further on the iOS section of that guide, that doesn't seem likely and I will follow your advice and enter an enhancement request.

WebKit-based Apps

To enable the developer tools in a WebKit-based application other than Safari, enter the following into the Terminal:

defaults write com.bundle.identifier WebKitDeveloperExtras -bool true

Replace

com.bundle.identifier