Hello Ginger,
Thank you for posting to the Microsoft Q&A forum.
To better understand the issue, could you please clarify the following?
- What type of account are you using in Classic Outlook: Outlook.com, Gmail, Yahoo, or another email provider?
- When you set a different address in “Options” > “Direct Replies To”, do recipients receive your message successfully and then reply to the original sender address instead?
- Does this happen with all recipients or only specific recipients?
- What version of Classic Outlook are you using? (Go to “File” > “Office Account” > “About Outlook”.)
As an initial test, please create a new email, select “Options” > “Direct Replies To”, enter the alternate reply address, send the message to a second email account that you own, and then use “Reply” from the received message. Let me know which address Outlook automatically fills in as the recipient of the reply.
Looking forward to your update.