Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello,
Outlook 2019 is not too old. Yahoo works fine in it, but you must use a Yahoo app password and set the account up as IMAP. The Add Account window will not show a Yahoo button, that is expected. Do this once and it will sync normally.
First create a Yahoo app password. In a web browser sign in to your Yahoo Mail account. Open Account Info > Security. Turn on two-step verification if Yahoo asks for it, then click Generate app password. Choose Outlook Desktop, copy the 16 character code, and keep that page open so you can copy it again if needed.
Now add the account in Outlook 2019. Open Outlook. Go to File > Account Settings > Account Settings > New. Choose Manual setup or additional server types. Pick POP or IMAP, then choose IMAP. Enter your name and your full Yahoo email address. For Incoming mail server type imap.mail.yahoo.com. For Outgoing mail server type smtp.mail.yahoo.com. For Password paste the Yahoo app password you generated, not your normal Yahoo sign in password.
Before finishing, click More Settings. On the Outgoing Server tab check My outgoing server requires authentication and leave Use same settings as my incoming mail server selected. On the Advanced tab set Incoming server (IMAP) to 993 and use SSL/TLS. Set Outgoing server (SMTP) to 465 and use SSL/TLS. Click OK, then Next, let Outlook test the settings, and Finish.
If you must use POP instead of IMAP, use
pop.mail.yahoo.comon port995withSSL/TLSfor Incoming, keepsmtp.mail.yahoo.comfor Outgoing, and keep the app password. IMAP is recommended because it keeps mail and folders in sync across devices like your iPhone.
If the test fails, the most common cause is accidentally using your normal Yahoo password. It has to be the special app password. Try the steps again and let me know exactly where it fails and what error you see, and I will tailor the next steps.