When sending encrypted mails using Apple Mail, how can I enable "encrypt to self"?

Question

Level 1

9 points

When sending encrypted mails using Apple Mail, how can I enable "encrypt to self"?

When sending encrypted mails using Apple Mail, how can I enable "encrypt to self" in order to be able to read what I sent later from within my "Sent" folder?

I'm looking for a toggle option similar to this:

https://gpgtools.tenderapp.com/kb/gpgmail-faq/gpgmail-hidden-settings#disable-en cryption-to-self

When testing I noticed that even if I send an encrypted mail to myself, I can't read that and just receive the smime.p7m attachment, the same that I get in all encrypted mails that I send). So the workaround of adding myself as bcc for all encrypted mails don't work either.

I would be willing to use the GPG Suite, but only if Apple Mail does not have such a feature out of the box.

Any hints are appreciated.

MacBook Pro, macOS High Sierra (10.13.3)

Posted on Mar 1, 2018 3:49 AM

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Answer 1

MoonJ.

Community Specialist

Mar 1, 2018 4:13 PM in response to oIiver

Hi oIiver,

Thanks for reaching out in Apple Support Communities. I understand that you're unable to read encrypted messages you send to yourself and you're unable to see the contents of encrypted messages you've sent. I know this is an important feature to use; I'd like to help. To begin I'd recommend reviewing the information below:

If you receive an email that Mail 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. For more information, 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. For more information, see Use personal certificates in Mail.

If Mail can’t decrypt messages

You may also want to check that your email address is properly associated with your certificate:

Note: If for some reason your certificate isn’t associated with your email address, or if you want to use your certificate with a different email address, Control-click the certificate in Keychain Access, choose New Identity Preference, and provide the requested information.

Sign or encrypt messages for increased security

Let me know what you find.

Best Regards.

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Answer 2

Leanne_68

Community Specialist

Mar 2, 2018 9:28 AM in response to oIiver

Hi oIiver,

Thank you for clarifying that. Based on the information you've provided, at this point I'd recommend reaching out to Apple for further assistance: Contact Apple Support

Best Regards.

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Answer 3

oIiver Author

Level 1

9 points

Mar 1, 2018 11:12 PM in response to MoonJ.

Thanks for trying to help MoonJ.

There is nothing wrong with my digital certificate or private key.

The problem is, that my own public key is not added (in addition to the one for the receipient) when I send out encrypted mails. This feature is commonly called "encrypt to self" and is apparently disabled by default in Apple Mail. Enabling it would allow me (in addition to the receipient) to read the content of encrypted mails I send out.

My hope is, that someone knows the commandline switch required to enable the "encrypt to self" feature in Apple Mail.

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Answer 4

oIiver Author

Level 1

9 points

Mar 3, 2018 12:39 AM in response to Encryptor5000

Hi Encryptor5000

I'm using the Apple Mail built-in feature (S/MIME variant) with a certificate and private key.

I might have added to the confusion when talking about "my public key" in my response to MoonJ. The correct term would have been "certificate".

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Answer 5

Mar 2, 2018 2:49 PM in response to oIiver

Hi Oliver,

What cryptosystem are you using for Mail? Are you using S/MIME (which relies on certificates & private keys) or PGP (which relies on public keys and private keys, not built into Mail)?

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Answer 6

oIiver Author

Level 1

9 points

Mar 3, 2018 12:30 AM in response to Leanne_68

Thanks Starr.C

I will reach out to Apple Support should I not get anything useful from the community within a week or two.

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When sending encrypted mails using Apple Mail, how can I enable "encrypt to self"?

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