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System keychain prompt when sending email.

I have a certificate associated with one of my Mail accounts. When I send an email using this account, I am repeatedly prompted to enter my username and password. The dialogue box says "Mail wants to make changes. Enter an administrator's name and password to allow this. Mail wants to use the System keychain." This prompt occurs periodically while I am composing the email and exactly three times in succession after selecting send.


I've dealt with this for years under many versions of MacOS, tried most of the the recommendations I could find online, and done several trouble calls with Apple support. There was a recent post with what seems like the same issue to which the accepted response was "remove the certificate or reinstall with the correct permissions." Removal is not an option for me and I'm not sure what would be needed to reinstall with the "correct" permissions.


Any help is appreciated. Thank you.

Posted on Apr 7, 2023 4:38 PM

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Posted on Apr 9, 2023 11:28 AM

Sounds like the certificate is in the System Keychain when it should be in the Login Keychain in My Certificates. Whenever something accesses the System Keychain you will be prompted for authentication but not in the Login Keychain.


Can you copy or move the certificate you use to encrypt your Mail account to the Login Keychain -> My Certificates? That is the proper location where it should be stored.





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Apr 9, 2023 11:28 AM in response to shawn.kern

Sounds like the certificate is in the System Keychain when it should be in the Login Keychain in My Certificates. Whenever something accesses the System Keychain you will be prompted for authentication but not in the Login Keychain.


Can you copy or move the certificate you use to encrypt your Mail account to the Login Keychain -> My Certificates? That is the proper location where it should be stored.





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May 12, 2023 4:45 PM in response to shawn.kern

I was able to overcome this issue. Originally, when double clicking the certificate, the Keychain Access Add Certificate dialog box did not include a keychain selection option. I reset my default keychains (Keychain Access > Settings) and the Add Certificate dialog box, after the reset, included a keychain selection. I selected the login keychain for the import. This has resolved the repeated password prompts I was seeing before.

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System keychain prompt when sending email.

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