Before you begin
We've shown how to create digital signatures in Preview, but there's a similar feature in Mail. When Mac OS X Yosemite launched back in 2014, Mail gained the ability to sign documents, such as PDF. How to Electronically Sign a PDF Using Preview on Mac. A program that comes preinstalled on every Mac running OS X Lion or later. If you are using the trackpad to create your electronic.
You can use S/MIME certificates, also called 'S/MIME Certs' or 'Personal Certificates', with most email clients to digitally sign and/or encrypt email messages. At Indiana University, S/MIME certificates are provided by the InCommon Certificate Service. For instructions on getting a certificate, see Get an S/MIME certificate for digital email signatures at IU.
When you receive your certificate from InCommon, it will be encrypted in the PKCS 12 format (
.p12
or .pfx
), using the strong passphrase ('PIN') you created for it at the time of request. You will need this passphrase to install the certificate.Also, for details about potential issues with various devices and applications when using digital signatures, be sure to refer to Known issues with digitally signed email at IU.
View a video about using digital signatures in Apple Mail and Outlook for macOS.
Install in macOS
- Double-click the file downloaded from the InCommon Certificate Manager.
- Keychain Access will prompt you for the certificate passphrase; use the second, 'PIN' passphrase, not the first 'request' passphrase.
The certificate will be installed on your Mac and will appear in the 'My Certificates' section of Keychain Access. The certificate is now available for Apple Mail, Outlook, and other applications that can use client certificates.
Your certificate is only available on the computer and user account where you install it. If you want your personal certificate on other computers or devices, you will need to import it on those devices also.
Use your certificate with Apple Mail
Use these instructions to enable Apple Mail to use client certificates to digitally sign and encrypt email.
Enable digital signing and encryption
- If you have just installed your certificate on your Mac, close Mail and then restart it.
- Begin composing an email message. You should see the 'Signed' icon () in the lower right of the message header (this indicates the message will be signed). If you don't see the 'Signed' icon, select Customize (in the lower left of the message header), and add the 'Lock' and 'Signed' icons.
Sign email
To send a signed message, verify that the 'Signed' icon has a checkmark (
✔
) in it . If the 'Signed' icon has an x
instead, your message will not be signed.You may not want to sign messages to mailing lists, because S/MIME digital signatures are attachments, which some lists do not accept.
Encrypt email
If you have the public certificate for the user or users to whom the messages is addressed, you will be able to encrypt the email message: In the lower right of the message header, click the open lock icon to lock it; when the icon is locked, your email message will be encrypted.
If you do not have certificates for everyone to whom the message is addressed, you will be prompted to send the message unencrypted.
Use your certificate with Outlook for macOS
Use these instructions to enable Outlook to use client certificates to digitally sign and encrypt email.
Enable digital signing and encryption
- If you have just installed your certificate on your Mac, close Outlook and then restart it.
- From the Outlook menu, select Preferences > Accounts. Select your IU email account, click Advanced, and then select the Security tab.
- In the 'Digital signing' section, select your certificate from the drop-down menu.
- For 'Signing algorithm', the default value of SHA-256 is appropriate for most situations.
- For the best usability, enable the following options:
- Sign outgoing messages
- Send digitally signed messages as clear text
- Include my certificates in signed messages
- In the 'Encryption' section, select your certificate from the drop-down menu.
- For 'Encryption algorithm', ASE-256 is the best option. It is not necessary to check Encrypt outgoing messages; each email message can be optionally encrypted when you compose it.
- IU does not currently use the 'Certificate authentication' options, so do not set this.
- Click OK to save your changes and exit Outlook Preferences.
Sign email
By default, your email messages will be digitally signed. To indicate signing, a lock icon with the text 'This message will be digitally signed' will appear in the lower left of the message header when you compose an email message:
If you do not want to sign a message, from the Options tab of the mail message, click Sign so that it is not selected.
You may not want to sign messages to mailing lists, because S/MIME digital signatures are attachments, which some lists do not accept.
Encrypt email
Address and compose your email message. From the Options tab of the mail message, click Encrypt so that it is selected.
If Outlook is unable to find certificates for everyone to whom the message is addressed, you will be prompted to search the IU Active Directory for user certificates. If Outlook is still unable to find certificates for all addressees, you will be prompted to send the message unencrypted.
Use a group account certificate
To use an S/MIME certificate with a group account, install and enable the certificate as you would for a standard account.
- If the profile you are using in your email client is the group account, there should be no issues.
- If the profile you are using in your email client is your personal account and you want to send email from the group account, in your email message, open the 'From' field and enter the group account address. If your personal account has 'send as' rights for the group account, there should be no issues. If you are unsure whether you have 'send as' rights, contact your IT Pro.
When you receive a PDF document by email that you must sign, the process of printing out the file, signing on the dotted line with a pen, scanning the signed document and sending it back can be a rather tedious task. Fortunately, Apple has added the ability to electronically sign a PDF document using Preview, a program that comes preinstalled on every Mac running OS X Lion or later.
The steps involved to electronically sign a PDF using Preview on Mac are quite simple and will save you valuable time, especially if you have multiple documents, contracts, forms or other paperwork to sign. If you are worried that your virtual signature will look bad, rest assured that you can create your signature by using the trackpad or holding up your signature on paper to a Mac's built-in iSight camera.
Steps to Electronically Sign a PDF Using Trackpad
- Open the PDF file you need to sign in Preview.
- Click on the Markup icon () and then the signature () icon.
- Click on Create Signature >Click Here to Begin. Draw your signature on the trackpad. Click any key when finished. Click Done.
- Click on the signature created to insert it into the PDF document. The signature can be moved or resized like a regular image.
Steps to Electronically Sign a PDF Using Camera
- Open the PDF file you need to sign in Preview.
- Click on the Markup icon () and then the signature () icon.
- Click on Create Signature >Camera. Sign your name on white paper and hold it to be visible to the camera. Preview will draw a virtual signature. Click Done.
- Click on the signature created to insert it into the PDF document. The signature can be moved or resized like a regular image.
Tips
- If you are using the trackpad to create your electronic signature, it is recommended that you look at Preview and go slow and steady with your finger to achieve the best result. For an even more precise signature, you can use an iPhone or iPad stylus, preferably one with a fine-tipped ending, to draw your signature on the trackpad.
- Signing a piece of white paper and holding it up to the camera is the easiest way of creating an electronic signature in Preview, although this method does not always yield the best results. The signature will appear inverted when you hold it up to your Mac's camera, but Preview will automatically ensure that it reads properly from left to right.
- You can create an electronic signature in Preview by following steps above even if you do not have a PDF document opened. By default, all electronic signatures that you create are automatically stored in a list on Preview so that you can insert them into future PDFs documents and other files without needing to repeat these steps. Preview can store multiple signatures at once.
- Apple also provides markup tools in the Mail app in macOS to create electronic signatures that can be directly inserted into your emails.
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