Signed and encrypted message replies and forwards sent by iOS 5 do not appear signed and encrypted

Question

Signed and encrypted message replies and forwards sent by iOS 5 do not appear signed and encrypted

Hello there,

I have a new iPad with iOS 5.1.1, The answer on this problem is update to iOS 5.1 or higher, however the problem is still here. When I send out digitally signed message from the default mail client of iPad to an Exchange 2010 recipient. The recipient side with Outlook 2010 doesn't recognize it as a signature, just the attachement appears as an unknown file (smime.p7s).

If I use my Outlook 2010 client to send out mail with the digital signature it is appearing properly (with the red ribbon) at the recipient Exchange 2010 mailbox. Do we have a real resolution or workaround for this?

Thanks,

Csaba

iPad (3rd gen) Wi-Fi + Cellular, iOS 5.1.1

Posted on Jun 28, 2012 9:33 AM

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Answer 1

Jun 28, 2012 9:43 AM in response to ProximaCentauri

This may provide some assistance:

http://support.apple.com/kb/HT4977?viewlocale=en_US&locale=en_US

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Answer 2

Jun 28, 2012 10:38 AM in response to Kilgore-Trout

The steps described at the above link don't work at all. That was the first thing I checked. It seems to be for me iOS does't send out the signature correctly. I'm using my gmail account as Exchange mailbox configured on the iPad and turned on Smime and signature. The cert and the chain installed correctly. If I send out a mail with the same certificate to another exchange mailbox with Outlook 2010 on my notebook, it's fine. If I send it out from the iPad, Outlook desn't recognize it, just shows the attachment like any client which dosn't support Smime. Something is really wrong here. :-(

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Answer 3

Jun 28, 2012 2:38 PM in response to ProximaCentauri

Hi Folks,

I've made some other tests:

1. Gmail account configured as Exchange mailbox on the iPad (the only reason for this config is to able to sync contacts as well)

2. Certificate installed, SMIME and digital signature turned on

3. Sending out a digitally signed mail to exchange recipient

4. Recipient client (Outlook 2010) cannot recognize the mail as a signed message, an attachment appears with name smime.p7s

5. Sending out digitally signed mail and read it on an iOS device

6. Same behavior as in point 4.

7. Configuring gmail account as Gmail mailbox on iPad (no option to sync contacts)

8. Turn SMIME and Sign on at the above mailbox on iPad

9. Send out a digitally signed mail to iOS and Outlook 2010 clients.

10. Everything is fine, the mail recognized as a signed message on both type of clients

This seems to be a bug with SMIME support on iOS 5.x.x when configuring gmail account as Exchange mailbox. Does anyone know how to address this to Apple to fix?

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