keychain password problem

Inexplicably, I am unable to send messages on my iMac using one of my two email accounts. When i try to send the message I am told "Mail wants to sign using key 'privateKey' in your keychain," and that "To allow this, enter the 'login' keychain password." Forgive my cluelessness, but I have no idea what this means, nor how to proceed.

iMac 21.5″, macOS 10.13

Posted on Mar 23, 2023 10:38 AM

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Posted on Mar 23, 2023 10:59 AM

It sounds like that particular e-mail account is configured to automatically digitally-sign your outgoing e-mails. (This is a “normal” setup, albeit not always requirement on many systems)


To “sign” an e-mail, your private key must be accessed from your keychain by your e-mailing software.


Since private keys are quite “security-sensitive” you are receiving the alert.


The password being requested is most likely your Apple ID password. (alternatively, it could possibly be the local password you use to startup your Mac’s account)


Your available options then are:


Stop signing the emails. (Usually a configuration option in your email’s settings)


Enter your password each time.

2 replies
Question marked as Top-ranking reply

Mar 23, 2023 10:59 AM in response to coffeyfromnull

It sounds like that particular e-mail account is configured to automatically digitally-sign your outgoing e-mails. (This is a “normal” setup, albeit not always requirement on many systems)


To “sign” an e-mail, your private key must be accessed from your keychain by your e-mailing software.


Since private keys are quite “security-sensitive” you are receiving the alert.


The password being requested is most likely your Apple ID password. (alternatively, it could possibly be the local password you use to startup your Mac’s account)


Your available options then are:


Stop signing the emails. (Usually a configuration option in your email’s settings)


Enter your password each time.

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keychain password problem

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