For those of us who struggle to have Voiceover read a password as you type it into a secure text field. I found a work-around to read aloud my password, as I type it
Open a new Apple note, type in your password, which VoiceOver will read out loud as you type your password, then open the Voiceover rotor to use Text Selection to select only your password, make sure that only your password is selected and that nothing else, is selected, including any spaces before and after your typed password, then copy the selected text.
Now go to your web page that is requiring your password, and paste your password into the secured text field box; Make sure Voiceover cursor is inside text field box, then paste your password into it.
I have already tried it and it is working for me. Unfortunately, Voiceover will not read, or even announce, the keyboard keys as you type. in any secure text field, which can be a real challenge. So I found a way around this and hope other Voiceover users will find this helpful. It would be great if Apple would allow an radio button to click on in Voiceover's Settings that would allow users to choose for themselves if they want voiceover to read aloud passwords as they type. It would be very helpful and appreciated if they did.