Autofill with sudo fails in Terminal.app and iTerm.app

Hello @brentward! 👋

I'm sorry that you're unable to fill your Mac admin password into the Terminal when using certain sudo commands. You mentioned the following:

I don't see the special password cursor when I run a sudo command

Do you mean that you don't see the key icon which looks like this:

Is it possible to temporarily turn off the policy plug-ins that your organization uses to narrow down the cause of the issue? If it isn't then can you ask your organization's IT department why the password icon (cursor) isn't appearing when you run certain sudo commands? This will likely point us in the right direction.

I look forward to hearing from you. 🙂

-Dave