1Password problems generating new passwords and updating websites

Hey Derek,
Thanks for taking the time to describe your issue in such a detailed manner.

The Safari extension works a bit differently than in other browsers, and we hope to indeed improve things in the next iteration of 1Password which is currently under development.

First, I'd like to point out that whenever you apply a new password on a website, whether by selecting the suggested password or by clicking on "Save & Copy" in the generator, the new password will automatically be saved in your 1Password 7 app under the "Passwords" category of your default vault for saving. So if you ever find yourself in a situation where the new password is lost:

1. Open your 1Password 7 desktop app.
2. Switch to your default vault (or switch to "All Vaults" if you're not sure which one is the default).
3. Click the "Passwords" category on the left sidebar and find the password there, stored as a "Password" item (an item with a grey key icon).

If you encounter a website where filling a new password into the "New Password" field and sending the form does not trigger the save/update prompt, you can trigger that prompt manually by clicking the 1Password extension icon in Safari's toolbar, then selecting the grey gear icon on the top right area of 1Password's window and choose "New Login". That will trigger the save/update prompt on the spot.

When you copy a password from 1Password, it will remain in your clipboard for a certain amount of time and then it will be wiped out from the clipboard, which is a security mechanism that you can adjust in the desktop app's preferences -> Security tab. Simply adjust the time in seconds to keep things in the clipboard before removing them, so that you may still paste the same password you have in the clipboard beyond the default 30-60 seconds.

If you'd like to try something new that might significantly improve your experience, I'd recommend you give 1Password 8 beta a try, alongside the new "1Password for Safari":

1. Install 1Password 8 beta: https://1password.community/discussion/122136
2. Go to the App Store and download "1Password for Safari".
3. Give your Mac a restart for good measures, then test and see how things work then.

With the new 1Password for Safari, when you select a new suggested password, it will immediately trigger the save/update prompt. Not only that, you can also set the default suggestions in the extension's generator and it will apply on the inline menu's suggestions when you visit websites.

I hope you'll find this helpful :)