To sign a financial grant form in PDF, I was required to download Adobe Reader and sign up for an AdobeID account that gives certified digital signatures on PDF’s. Since then, I can’t send an email without this message popping up and requiring me to enter my admin password TWICE. Can’t find any Mail preference to undo it. If I deny the access it won't send my email.
MacBook Pro 16", macOS 10.15
Eureka, I found two possible solutions.
The permanent solution: Open Keychain Access on your Mac. Select Login from the upper left menu and select MyCertificates from the lower left menu. On the right, you'll be able to see any certificates saved in your keychain. Find the offending certificate. Click the arrow to expand folder content. Right click to delete it from your Keychain. If you're nervous about deleting the certificate, you could export a copy to your downloads folder first as back up. Now that I've deleted the Adobe certificate, Mail has returned to normal behaviour.
There is also a less permanent workaround in Mail. If encription is turned on in Mail via login keychain settings, there will be a blue star icon below the subject line when you compose a new email. Click that star. It will grey out with a x mark. Mails will send normally, however this might inadvertantly disable any other digital mail signing that you actually do want or need attached to outgoing emails.
Eureka, I found two possible solutions.
The permanent solution: Open Keychain Access on your Mac. Select Login from the upper left menu and select MyCertificates from the lower left menu. On the right, you'll be able to see any certificates saved in your keychain. Find the offending certificate. Click the arrow to expand folder content. Right click to delete it from your Keychain. If you're nervous about deleting the certificate, you could export a copy to your downloads folder first as back up. Now that I've deleted the Adobe certificate, Mail has returned to normal behaviour.
There is also a less permanent workaround in Mail. If encription is turned on in Mail via login keychain settings, there will be a blue star icon below the subject line when you compose a new email. Click that star. It will grey out with a x mark. Mails will send normally, however this might inadvertantly disable any other digital mail signing that you actually do want or need attached to outgoing emails.
Hi blazedj420,
Welcome to Apple Support Communities. I understand you're seeing a consistent pop up notification of the login keychain for the Mail app on your computer.
I know how important it is to seamless experience on your Mac. I'll be happy to help.
To help troubleshoot this behavior, I recommend to follow the steps outlined in this helpful article: If your Mac keeps asking for the login keychain password This can help resolve the issue you're experiencing.
Cheers.
blazedj420,
Thanks for getting back to us and for letting us know.
To help isolate this behavior further, I suggest to restart your Mac in safe mode: How to use safe mode on your Mac In addition, you want to make sure that you have permission to update the keychain under your user account. Here's a helpful article with the proper steps: Change permissions for files, folders, or disks on Mac
From there, see if you can follow the steps in the article that was previously advised: If your Mac keeps asking for the login keychain password
Please let us know if that helps.
Kind regards.
Tried to follow the directions in the above link, but when I select 'login' and and go up to the edit menu bar, the 'change password for keychain 'login'' is there in the dropdown, but it's not highlighted highlightable and not selectable.
I have this problem to. It only started after being forced to create an Adobe certificate. This advice from Apple doesn't solve this specific problem.
I had the same issue once before a couple of years ago, but can't remember how I resolved it. There was something that needed deleting deep in a library somewhere. Help! I can't send emails at all at the moment.
Mail asking for 'privateKey' password after installing Adobe Reader
