Can't encrypt email. "Identity could not be found"

Question

Level 1

55 points

Can't encrypt email. "Identity could not be found"

iPad Air 2,iOS 9.1

and iPhone 6, iOS 9.1

Mail will not allow me to ecrypt an email to myself. I have installed my certificate and able to sign messages. When I attempt to encrypt, I get this:

Unable to Encrypt: You can't send encrypted messages because an encryption identity for the address [From:] could not be found. Go to the advanced settings for the account to choose an identity.

When I go to those settings, my certificate is already selected. I've rebooted both devices to no effect.

I foolishly took this to an Apple Support Chat, where the rep told me to add my account as an Outlook or Exchange account, rather than Other, among other idiotic suggestions. Any ideas? I really, really, really don't want to remove and reinstall this email account.

Thank you,

Aaron

iPad Air 2 Wi-Fi, iOS 9.1

Posted on Nov 14, 2015 12:26 AM

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Answer 1

Nov 18, 2015 2:59 PM in response to Fvutvutvtuv

I also have this issue. iPhone 6 iOS 9.1. It also happens if I try to encrypt email to others whose certificates I have added into my phone. I have tried re-adding the account and the same error still occurs.

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Answer 2

Nov 18, 2015 3:18 PM in response to JoeGomez17

After struggling with this for a while I managed to fix it.

Even though I exported the certificates as a package from my computer including my public cert, intermediate certs, root cert, and private key, and imported that into my phone, the iPhone fails to install the private key.

Here is what I did:

-Export your private key *only*

-Email it to yourself or get it to your iPhone in some way

-Install your private key

-Restart your iPhone / restart your mail application.

I can now sign and encrypt email.

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Answer 3

Fvutvutvtuv Author

Level 1

55 points

Nov 18, 2015 10:25 PM in response to JoeGomez17

I have a pfx certificate, which I understand is a package containing my public and private keys. How do I extract my private key only in a compatible format? I have found OpenSSL but it only exports in .pem format, which iOS doesn't support.

I've figured out the iPGMail app. It's not pretty, and it requires manual copying of messages to and from the mail app, but it works which is more than I can say about Mail and Apple's support for the CA certificate on which I wasted $25.

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Answer 4

Nov 19, 2015 12:14 PM in response to Fvutvutvtuv

Alright, if that wasn't working then try this - I wiped out my phone and completely tried again and ran into the same error.

-I added my mail account

-I imported my certificate .pfx

-I then went to Settings > Mail Contacts Calendar > My Mail Acct > Account > Advanced Settings > Signing > Set signing to Enable

-I was able to sign an email, but when I tried to encrypt one it would say Unable to Encrypt: You can't send encrypted messages because an encryption identity for the address [From:] could not be found. Go to the advanced settings for the account to choose an identity.

Instead of doing certificate funkiness, I did this:

-Went back into Settings > Mail Contacts Calendar > My Mail Acct > Account > Advanced Settings > Encrypt by default

-I set the "Encrypt by Default" to On and chose my cert. Even though I don't want it to encrypt by default.

Then I closed and opened Mail. I could now send encrypted mail.

I then went back and disabled the Encrypt by Default and Encrypting mail still worked, but was not forced to try and encrypt to everyone I was sending to.

Keep in mind that in order to send someone encrypted mail you need to (one time):

-Have them send you a signed email

-Click on their name with the checkmark by it in the signed email

-Click on View Certificate

-Click install

That will install their public key/cert to your iOS device and let you encrypt to it.

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Answer 5

Fvutvutvtuv Author

Level 1

55 points

Nov 19, 2015 1:47 PM in response to JoeGomez17

Now it can't find my certificate even to sign.

I had already uninstalled my certificate last night before oowering off my phone. I reinstalled the cert, turned on signing, but now I can't sign or encrypt.

Are you testing this on a non-exchange account? I'm using an IMAP config for an account at Runbox.com.

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Answer 6

Nov 19, 2015 7:03 PM in response to Fvutvutvtuv

I have two accounts on my iPhone and iPad now that use S/MIME, one is connected to a Zimbra server but is setup as "Exchange" on the iPhone, and the other is setup as Google (gmail).

Maybe try to export your certificate and private key again. I had that same problem once and I went to my computer and made sure I exported everything.

Also try to delete any bad profiles first in Settings > General > Profiles.

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