strange S/MIME behavior

Question

strange S/MIME behavior

I've generated several self-signed certificates to use with my various email accounts and transferred them to my iPhone using the iPhone configuration utility.

One of the accounts is set up such that I can choose from different identities.

To check whether everything works ok I tested a few possibilities using the same accounts to sent and receive emails (i.e. user1@mymail.com to user1@mymail.com). The following three work as they should.

- encrypted mail sent from the iPhone and read on a MBP OK

- encrypted mail sent from the iPhone and read on the iPhone OK

- encrypted mail sent from the MBP and read on a MBP OK

Now the fun starts:

- encrypted mail sent from the MBP and read on the iPhone FAILS

It fails with the following message: Decryption Error. This message is encrypted. Install a profile containing your encryption identity to decrypt this message"

Sending messages from different accounts to the affected account (i.e. user2@myothermail.com to user1@mymail.com) works flawlessly.

Any hints will be appreciated.

TIA

Posted on Oct 11, 2012 7:30 AM

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Answer 1

jrc-__

Level 1

4 points

Jan 12, 2013 11:33 PM in response to macuser222222

I think I found the problem: the sender's public certificate isn't getting automatically installed in iOS 6.

On the iPhone, go to a signed email and tap the sender's name (which has the little blue "signed" checkmark seal). It should say "Signed - The sender signed this message with a trusted certificate". Tap the [View Certificate] button immediately under that. The certificate should say "Trusted". Tap the [Install] button. Nothing happens; the button simply toggles between Install and Remove. But that's the trick. Now you should be able to decrypt encrypted messages and also send encrypted messages to that same contact.

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Answer 2

Feb 9, 2013 6:38 AM in response to jrc-__

You are right, the certificates are not automatically installed.

However I did what you described when I installed the certificates. The issue still exists. It would be nice if there were a way to see what certificates are installed on the iPhone. I could then try to check and/or remove these certificates.

I do have the feeling that the iPhone's mailer cannot handle multiple identities connected to the same account thouroghly even if there is only a single identity that uses encryption.

Another weird thing on the iPhone is that whenever you pass a link (or website) from Safari or Opera to the mailer there is no way to encrypt or sign the message. This is only possible if you create a mail from inside the mailer.

As a work around for the first problem I simply use a different mail address but this is not really satisfactory.

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