I quite accidentally created a private key when e signing a document. Now Mac mail will not let me send anything at all or even accept my keychain log in to allow or deny. I have followed instructions and deleted all certificates but I’m still hitting a wall and cannot send e mail. Any suggestions?
iMac 27″, macOS 12.6
Hey there kellyfromeverett,
Thanks for reaching out to the Apple Support Communities.
Just to confirm, from the information you've provided it sounds like you may have encrypted an email, does that sound correct? More details about encrypting emails can be found at this link here: Sign or encrypt emails in Mail on Mac - Apple Support
If you've removed the digital certificates, your private key may be missing from keychain. Check out the steps in these next resources below that can provide more information on decrypting emails, and help with obtaining and using personal certificates in the Mail app:
If Mail on your Mac can’t decrypt emails - Apple Support
If you receive an email message that the Mail appon your Mac can’t decrypt, it’s possible your digital certificate or its private key is missing from a keychain. Try these suggestions.
- If you have a backup of your keychain (created when you export your digital certificate and private key), import the Personal Information Exchange (.p12) file. See Import and export keychain items.
- If your digital certificate and private key are stored on a Common Access Card (“smart card”), insert the card in your Mac, then try again.
- If you no longer have your digital certificate or its private key, obtain a new certificate. See Use personal certificates.
Use personal certificates in Mail on Mac - Apple Support
If you want to send and receive signed and encrypted messages in the Mail app
Step 1: Obtain a certificate
For each email address you want to use to send signed messages and receive encrypted messages, you must get a certificate from a certificate authority (CA). See Request a certificate from a certificate authority.
Step 2: Import the certificate
To import the certificate into Keychain Access, double-click the certificate file you received from the CA. Once you import your certificate, it should be listed in the My Certificates category in Keychain Access.
The certificate file must have a file extension that indicates it contains certificates—such as .cer, .crt, .p12, or .p7c—or Keychain Access can’t import it.
If Keychain Access can’t import the certificate, try dragging the file onto the Keychain Access icon in the Finder. If that doesn’t work, contact the CA to ask if the certificate is expired or invalid.
Step 3: Use the certificate
Open your certificate in Keychain Access and make sure its trust setting is Use System Defaults or Always Trust. Now you can use the certificate to send and receive signed and encrypted messages.
Note: If for some reason your certificate isn’t associated with your email address, or you want to use the certificate with a different email address, Control-click the certificate in Keychain Access, choose New Identity Preference, and provide the requested information.
To use your certificate on another Mac, import the certificate into Keychain Access on that Mac.
Let us know if that's able to help.
Take care!
Hey there kellyfromeverett,
Thanks for reaching out to the Apple Support Communities.
Just to confirm, from the information you've provided it sounds like you may have encrypted an email, does that sound correct? More details about encrypting emails can be found at this link here: Sign or encrypt emails in Mail on Mac - Apple Support
If you've removed the digital certificates, your private key may be missing from keychain. Check out the steps in these next resources below that can provide more information on decrypting emails, and help with obtaining and using personal certificates in the Mail app:
If Mail on your Mac can’t decrypt emails - Apple Support
If you receive an email message that the Mail app
- If you have a backup of your keychain (created when you export your digital certificate and private key), import the Personal Information Exchange (.p12) file. See Import and export keychain items.
- If your digital certificate and private key are stored on a Common Access Card (“smart card”), insert the card in your Mac, then try again.
- If you no longer have your digital certificate or its private key, obtain a new certificate. See Use personal certificates.
Use personal certificates in Mail on Mac - Apple Support
If you want to send and receive signed and encrypted messages in the Mail app
Step 1: Obtain a certificate
For each email address you want to use to send signed messages and receive encrypted messages, you must get a certificate from a certificate authority (CA). See Request a certificate from a certificate authority.
Step 2: Import the certificate
To import the certificate into Keychain Access, double-click the certificate file you received from the CA. Once you import your certificate, it should be listed in the My Certificates category in Keychain Access.
The certificate file must have a file extension that indicates it contains certificates—such as .cer, .crt, .p12, or .p7c—or Keychain Access can’t import it.
If Keychain Access can’t import the certificate, try dragging the file onto the Keychain Access icon in the Finder. If that doesn’t work, contact the CA to ask if the certificate is expired or invalid.
Step 3: Use the certificate
Open your certificate in Keychain Access and make sure its trust setting is Use System Defaults or Always Trust. Now you can use the certificate to send and receive signed and encrypted messages.
Note: If for some reason your certificate isn’t associated with your email address, or you want to use the certificate with a different email address, Control-click the certificate in Keychain Access, choose New Identity Preference, and provide the requested information.
To use your certificate on another Mac, import the certificate into Keychain Access on that Mac.
Let us know if that's able to help.
Take care!
Private key Mac mail not working
