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S\MIME Encryption on Outlook

Posted on 2016-08-14
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Last Modified: 2016-09-24
hello,

We have enabled S\MIME encryption on outlook for some users but we are facing issue once we send signed message or encrypted that it is received as attachment. can we solve this ?

Regards,
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Question by:fadyaz
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Expert Comment

by:Alexei Kuznetsov
ID: 41755584
What email clients are on the recipient side?
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Author Comment

by:fadyaz
ID: 41755587
Outllok on windows

It is happened with all clients recipients on windows or phone.
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Expert Comment

by:David Johnson, CD, MVP
ID: 41758733
have you exchanged public keys? The recipient must have your public key
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Assisted Solution

by:btan
btan earned 250 total points (awarded by participants)
ID: 41763995
On mobile check
Enable S/MIME on the device

From the Windows Phone device perform the following steps:

Open the company email account.

Tap the … to open the menu window.

Tap settings.

Tap sync settings.

To sign messages with S/MIME, slide the Sign with S/MIME bar to the On position.

To encrypt messages with S/MIME, slide the Encrypt with S/MIME bar to the On position.

Tap the Check mark to save the sync settings.
https://msdn.microsoft.com/en-us/library/dn643699.aspx

Also check the EAS setting

Exchange ActiveSync mailbox policies let you apply a common set of policy or security settings to a user or group of users.

Enable S/MIME for Exchange ActiveSync following these steps:

Open the Exchange Management Shell
Run the command Get-Mobile

Verify that the policy settings in the following table are configured:
....
see any specific exchange errors and see if the user can to themselves to test as well.
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by:noci
noci earned 125 total points (awarded by participants)
ID: 41764211
Before you can encrypt you need to exchange public keys. And all devices you want to transmit from needs the private key for the mail address.

Be careful with hosted services, the SMTP sending device needs the keys, with hosted services the device is owned by the hoster (so it conectent is accessible to the hoster) , that hoster can disguise as you indistinguishable from you. So there is never security there, for some things like confidentiality the cloud, as such, is not a solution.
IMHO Windows 10 devices count as hosted devices as Microsoft reserved the right to upload anything from your device, that might include the private keys needed for encryption.
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Assisted Solution

by:btan
btan earned 250 total points (awarded by participants)
ID: 41764250
Do ensure the below certificate are installed e.g.
- Trusted root CA certificate (Computer certificate store - Root)
- User certificate (Include email address in subject name, Email address, User principal name (UPN)) stated in the cert and for your account cert store in the Certificates – Current User)

As a whole you need to setup the digital ID, based on how you get the certificate, you can provision SMIME as per the link

http://searchexchange.techtarget.com/tutorial/Using-S-MIME-in-Microsoft-Outlook
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Assisted Solution

by:David Johnson, CD, MVP
David Johnson, CD, MVP earned 125 total points (awarded by participants)
ID: 41764483
The easiest way to exchange keys is for each user in the conversation to send a signed message and each recipient double clicks the certificate and installs it.
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Author Comment

by:fadyaz
ID: 41782461
is this working on mac also?
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Assisted Solution

by:noci
noci earned 125 total points (awarded by participants)
ID: 41784379
If S/MIME is supported by your mail package Yes.
After the association of the email address with a public key (using a signed message)
Encryption can be used.  Note that your private key should always be with you, and never be uploaded to some web-based service unless you control (have physical owner ship & posession) of the system the service is placed on.
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Accepted Solution

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btan earned 250 total points (awarded by participants)
ID: 41784510
Mac outlook client support SMIME as long as you import the certificate (PFX for containing private key) into the Mac Keyring.

https://technet.microsoft.com/en-us/library/jj984223(v=office.16).aspx
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Expert Comment

by:btan
ID: 41813551
As shared and advised in the post.
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