If you're using an IMAP or POP3 account, such as a Yahoo or Google Gmail account, go to Send automatic Out of Office replies from Outlook for Mac and follow the steps under “View this if you have a Hotmail, Gmail, Yahoo! or other POP or IMAP account. If you're using a Microsoft Exchange account, go to Send automatic Out of Office replies from Outlook for Mac and follow the steps under “View this if you have an Exchange or account.” Your certificate is used to encrypt the copy that is saved to. Note: When you send an encrypted message, your recipient's certificate is used to encrypt his or her copy of the message. Finish composing your message, and then click Send. Then, on the left pane of the Accounts box, select the email account. In an email message, select Options > Security > Encrypt Message. To see which type of Outlook email account you have, open Outlook, and in the menu bar select Tools > Accounts.
This has worked for all Mac-related Office software, except when applied to individual emails on Outlook 2019.
The steps you'll follow will depend on whether you have a Microsoft Exchange Outlook email account (if you have email through an organization, such as the place where you work) or an IMAP or POP3 account (if you have an individual email account such as Yahoo or Gmail). According to Apple, control+click on any message to get the context menu available. Before you set up an out of office or automatic reply in Outlook, you'll need to know your Outlook account type.
