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Applies to
Windows 10
Windows 10 Mobile
S/MIME stands for Secure/Multipurpose Internet Mail Extensions, and provides an added layer of security for email sent to and from an Exchange ActiveSync (EAS) account. In Windows 10, S/MIME lets users encrypt outgoing messages and attachments so that only intended recipients who have a digital identification (ID), also known as a certificate, can read them. Users can digitally sign a message, which provides the recipients with a way to verify the identity of the sender and that the message hasn't been tampered with.
About message encryption
Users can send encrypted message to people in their organization and people outside their organization if they have their encryption certificates. However, users using Windows 10 Mail app can only read encrypted messages if the message is received on their Exchange account and they have corresponding decryption keys.
Encrypted messages can be read only by recipients who have a certificate. If you try to send an encrypted message to recipient(s) whose encryption certificate are not available, the app will prompt you to remove these recipients before sending the email.
About digital signatures
A digitally signed message reassures the recipient that the message hasn't been tampered with and verifies the identity of the sender. Recipients can only verify the digital signature if they’re using an email client that supports S/MIME.
Prerequisites
S/MIME is enabled for Exchange accounts (on-premises and Office 365). Users can’t use S/MIME signing and encryption with a personal account such as Outlook.com.
Valid Personal Information Exchange (PFX) certificates are installed on the device.
Choose S/MIME settings
On the device, perform the following steps: (add select certificate)
Open the Mail app. (In Windows 10 Mobile, the app is Outlook Mail.)
Open Settings by tapping the gear icon on a PC, or the ellipsis (...) and then the gear icon on a phone.
Tap Email security.
In Select an account, select the account for which you want to configure S/MIME options.
Make a certificate selection for digital signature and encryption.
Select Automatically to let the app choose the certificate.
Select Manually to specify the certificate yourself from the list of valid certificates on the device.
(Optional) Select Always sign with S/MIME, Always encrypt with S/MIME, or both, to automatically digitally sign or encrypt all outgoing messages.
Note: The option to sign or encrypt can be changed for individual messages, unless EAS policies prevent it.
Tap the back arrow.
Encrypt or sign individual messages
While composing a message, choose Options from the ribbon. On phone, Options can be accessed by tapping the ellipsis (...).
Use Sign and Encrypt icons to turn on digital signature and encryption for this message.
Read signed or encrypted messages
When you receive an encrypted message, the mail app will check whether there is a certificate available on your computer. If there is a certificate available, the message will be decrypted when you open it. If your certificate is stored on a smartcard, you will be prompted to insert the smartcard to read the message. Your smartcard may also require a PIN to access the certificate.
Install certificates from a received message
When you receive a signed email, the app provide feature to install corresponding encryption certificate on your device if the certificate is available. This certificate can then be used to send encrypted email to this person.
Open a signed email.
Tap or click the digital signature icon in the reading pane.
Tap Install.
Email security become major issue as a lot of viruses, spam, fishing attempts use this method as major platform to attack individual and organization, one way is to sign & encrypt you emails so the receiving part can be 100% sure you are the sender and the email content can be trusted . S/MIME stands for Secure/Multipurpose Internet Mail Extensions . The best way is to buy certificate from trusted authority or try getting one for free valid for one year from here : https://www.actalis.it/products/certificates-for-secure-electronic-mail.aspx
However in this tutorial I will Show how to create self-signed certificate with self Authority .Lets begin.
First you will need to install OpenSSL on windows, and you can download it from here : https://slproweb.com/products/Win32OpenSSL.html or from here : http://gnuwin32.sourceforge.net/packages/openssl.htm
all the command you should run from command prompt under the installation directory in BIN folder. Lets say you have install it to :
So run the command from :
First lets create Private key for our Authority :
enter password for the key. Next Lets create self-sign certificate for our private authority valid for 3650 (10 years) :
Fill al the information in the wizard in order to create the certificate using the password you have selected before for the private key .
Next lets create an RSA Private Key for the Personal E-Mail Certificate, again you will have to create password for the private key :
We should create a file called smime.cnf in C:OpenSSL-Win64bin , Create text file->change its name to smime.cnf and enter this content as template for the certificate :
Now we are ready to create CSR; Certificate Signing Request :
We now ready to create Certificate signed with our Private authority :
Now you have created self signed certificate with the Private authority, Although outlook and outher email client use p12 certificate style, Lets create this kind of certificate :
Enter the password you have created for the private key before . Now you have all the certificates you will need. in order to trust those certificates you will need to install them on the computer.
First install the ca.crt under Trusted Root Certificate authority as this will give the certificate validation, to do so :
Now Expand certificate and with the left mouse key import ca.crt to Trusted Root Certificate authority -> import smime_test_user.p12 under personal -> make sure the certificate is valid without errors
You shoud do it for both side computer, sender & receiver , is you have created self-signed on the receiver side this certificates should be install on all side (cert exchange) .
Installing the certificate on outlook as describe very nicely at https://www.ssl.com/how-to/installing-an-s-mime-certificate-and-sending-secure-email-with-outlook-on-windows-10 :
1. In Outlook, select File from the main menu, then click Options.
2. Select Trust Center at the bottom of the menu on the left side of the Outlook Options window.
3. Click Trust Center Settings.
4. Select Email Security from the left-hand menu of the Trust Center window.
5. Click Import/Export.
6. Make sure Import existing Digital ID from a file is checked, then click Browse…
7. Navigate to the PKCS#12 file, then click Open. The filename extension should be .p12.
8. Enter the password you used when downloading the PKCS#12 file, then click OK.
9. Click OK on the security dialog box that pops up.
10. Click Settings.
11. Enter a name for your security settings.
12. Click Choose, next to Signing Certificate. If you have only installed one certificate (as shown here), you can click OK on the Confirm Certificate dialog box that pops up. Otherwise, you will have to choose one from a list of installed certificates.
13. Click Choose, next to Encryption Certificate, and click OK on the Confirm Certificate dialog box. Again, if you have more than one certificate, select the same one you chose for Signing Certificate.
14. Click OK to close the Change Security Settings window.
15. Set your desired default options for S/MIME email via the four checkboxes under Encrypted email, then click OK to close the Trust Center Window.
The certificate is now installed and you can use it to digitally sign and encrypt messages in Outlook.
To send secure email in Outlook:
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1. Begin composing a new email message in Outlook. Under Options, you can toggle the encryption and/or digital signature settings for the message.
2. After sending, click Allow in the Windows Security dialog box that appears, allowing Outlook to use your private key.
3. Note that if you attempt to send encrypted email and do not have your recipient’s public key, you will get an error message giving the option to send the message unencrypted.
When trying to send encryped email you might get error : valid certificate :
To Fix this you can import the certificate smime_test_user.p12 :
You can import again from there again the certificate