Encrypted email

Question

Level 1

7 points

Encrypted email

Hi guys,

I ran into a problem with signed and encrypted emails on my iPhone (iOS 10.3.2). So I downloaded 3 Comodo certificates : 2 for work email addresses and 1 for my personal email address. Those certificates have been generated in exactly the same way.

From both work email addresses (Outlook clients) I can perfectly send encrypted emails to each other, and to my phone. So, no issue there.

However, from my iPhone (personal email) I can only send encrypted and signed emails to one of the 2 work addresses. I did install both public keys on my phone though (the incoming email addresses appear with a blue circle so I know they work). Already closed and re-opened the Mail app and rebooted my phone a few times. Also on my phone, I uninstalled/reinstalled the certificate for the email address that it refuses to send encrypted emails to. Afaik, all 3 mail servers are Exchange, but probably different versions.

In my Mail preferences (on iPhone) I enabled S/MIME, "always sign" and "always encrypt"
Any ideas on how I can send encrypted emails to that second work email address?

Thx !

iPhone 6s, iOS 10.3.2

Posted on Jun 23, 2017 12:50 AM

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Answer 1

anonyme4321

Level 6

17,269 points

Jun 23, 2017 1:43 AM in response to gstoelen

Go to Settings - General and then About.
Select Certificate Trust Settings.
Each root that has been installed via a profile will be listed below the heading Enable Full Trust For Root Certificates. You should be able to toggle on/off trust for each root.

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Answer 2

gstoelen Author

Level 1

7 points

Jun 23, 2017 1:38 AM in response to anonyme4321

Hi,

That's what I did initially, to get the certificate installed on the phone.. It does recognize the certificate because of the tick in the circle next to the source email address. When I check the properties, it says "Trusted" with a green tick. So I presume this is fine. The same goes for the other, working email address.

I'm just not sure about the certificate that is installed on the iPhone though. When I check the certificate status in Settings - General - Profile - <name of profile>, it states "Not Verified" in red..

That still doesn't explain why it allows me to send encrypted mails to one address, but not to the other though.

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Answer 3

gstoelen Author

Level 1

7 points

Jun 23, 2017 2:57 AM in response to anonyme4321

I removed the profile, then rebooted the phone. Then I installed the new certificate.

Still the same behavior though... I can perfectly receive and send encrypted mails to one of both email addresses, but right now I can't decrypt the problematic email address either. Getting the error "This message is encrypted. Install a profile containing your encryption identity to decrypt this message". I did already remove and reinstall the problematic email address' certificate on the phone though...

Not sure what to try next 😕

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Answer 4

gstoelen Author

Level 1

7 points

Jun 23, 2017 3:00 AM in response to anonyme4321

Oh yes - when I use webmail (using my phone's email address), I can read the encrypted email sent from the "problematic email address"... Both certificates are installed on that laptop though. Which leads me to believe that for some reason, the iPhone is not able to import the problematic email certificate ?

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Answer 5

gstoelen Author

Level 1

7 points

Jun 23, 2017 3:19 AM in response to anonyme4321

That's what I did. But now I can't decrypt emails on the phone that are coming from both other addresses 😁

I removed the senders' certificates on the phone, then sent a signed email from both addresses to the iPhone so I could reinstall the certificates again, but I'm not able to decrypt their messages on the phone. Puzzling..