Options Fields NOT Working

Question

Options Fields NOT Working

Ginger 0

Classic Outlook: The "Direct Replies to" under Options does NOT work

Ginger 0 Reputation points

2026-10-08T04:58:24.9366667+00:00

1.      MS Outlook for M 365 MSO version 26092.      I am using AT&T / Yahoo mail.

3.      I have tested using good email addresses that I can send to UNLESS I type any address into the “Direct Replies To” field.

4.      No one receives entries when I use the "Direct Replies To" field. The email address I SEND TO does not ever get the email so there is no way anyone can reply because no one gets an email if I populate the “Direct Replies To” field. Instead, I get Sys Admin undeliverable message:

       Subject:     test

      Sent: 10/3/2026 11:02 PM

The following recipient(s) cannot be reached:

      “The email address I entered in the “TO” field shows here '' on 10/3/2026 11:02 PM

            550 Request failed; Mailbox unavailable

It is a good address, and I can send to the exact same address IF AND ONLY IF I don’t use “Direct Replies To: field.

5.      II do understand the steps to take to use the “Direct Replies To” field.

6.      I have tried this using my PC as well as my husband’s PC (all same as far as versions, 365, etc.) It used to work for him but no longer – he has same issue as me.

7.      I have done an update of MSOffice products and tried again but same issue.

8.      Only test NOT done yet = safe mode (as of 10/7/26)Additional Info :
Emma1-N 13,685 Reputation points Microsoft External Staff Moderator

2026-10-09T00:56:37.7333333+00:00
Hello Ginger,

Thank you for the detailed clarification. Since normal sending works and the failure occurs only when “Direct Replies To” is populated, please complete the remaining Safe Mode test:

Close Outlook.

Press Windows + R, type outlook /safe, and press Enter.

Send a test message using “Direct Replies To”.

If the message sends successfully in Safe Mode, an Outlook add-in may be involved. If you still receive the same 550 error, please let me know.
Emma1-N 13,685 Reputation points Microsoft External Staff Moderator

2026-10-10T08:40:50.3266667+00:00

Hello Ginger,

Is there any update from you? Please let me know, I will be here to assist you.

2 answers

Your answer

Ginger 0 Reputation points

2026-10-08T04:58:24.9366667+00:00

1. MS Outlook for M 365 MSO version 26092. I am using AT&T / Yahoo mail.

3. I have tested using good email addresses that I can send to UNLESS I type any address into the “Direct Replies To” field.

4. No one receives entries when I use the "Direct Replies To" field. The email address I SEND TO does not ever get the email so there is no way anyone can reply because no one gets an email if I populate the “Direct Replies To” field. Instead, I get Sys Admin undeliverable message:

Subject: test

Sent: 10/3/2026 11:02 PM

The following recipient(s) cannot be reached:

“The email address I entered in the “TO” field shows here '' on 10/3/2026 11:02 PM

550 Request failed; Mailbox unavailable

It is a good address, and I can send to the exact same address IF AND ONLY IF I don’t use “Direct Replies To: field.

5. II do understand the steps to take to use the “Direct Replies To” field.

6. I have tried this using my PC as well as my husband’s PC (all same as far as versions, 365, etc.) It used to work for him but no longer – he has same issue as me.

7. I have done an update of MSOffice products and tried again but same issue.

8. Only test NOT done yet = safe mode (as of 10/7/26)Additional Info :
Emma1-N 13,685 Reputation points Microsoft External Staff Moderator

2026-10-09T00:56:37.7333333+00:00

Hello Ginger,

Thank you for the detailed clarification. Since normal sending works and the failure occurs only when “Direct Replies To” is populated, please complete the remaining Safe Mode test:

Close Outlook.

Press Windows + R, type outlook /safe, and press Enter.

Send a test message using “Direct Replies To”.

If the message sends successfully in Safe Mode, an Outlook add-in may be involved. If you still receive the same 550 error, please let me know.
Emma1-N 13,685 Reputation points Microsoft External Staff Moderator

2026-10-10T08:40:50.3266667+00:00

Hello Ginger,

Is there any update from you? Please let me know, I will be here to assist you.

Answer 1

Hornblower409 16,580

@Ginger

It's not Outlook, it's Yahoo. I just tested using my Classic Outlook and my ATT/Yahoo IMAP account. All the email addresses involved are valid. Anything with a Reply To (other than your own email) gets bounced.

User's image

To make the Reply-To work you have to:

1 -- Add the Reply-To address to your ATT account as a "Send-only email address"

See the "Add a new reply-to address" section in
[External Non-Microsoft Site] https://help.yahoo.com/kb/att/SLN28884.html

User's image

2 -- And you MUST go thru the steps to verify the address. Once it is verified, the "Not verified" flag is removed.

User's image

Now you can use that address in an Outlook Reply-To. It will be delivered and any replies will use the Reply-To address like it is suppose to.

User's image

Ginger 0 Reputation points

2026-10-08T05:38:19.62+00:00

You are AWESOME. Thanks for determining Yahoo as the culprit. And thanks for working on when/why Yahoo changed the rules. I look forward to hearing from you.

Thanks again,

Ginger
Hornblower409 16,580 Reputation points

2026-10-08T05:43:50.3433333+00:00

[2026-10-08 - Removed by author]
Hornblower409 16,580 Reputation points

2026-10-08T06:34:55.53+00:00

[2026-10-08 - Content moved into the Answer above by author]

Answer 2

Emma1-N 13,685 Microsoft External Staff Moderator

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.

Emma1-N 13,685 Reputation points Microsoft External Staff Moderator

2026-10-03T06:38:54.1933333+00:00

Hello Ginger,

I just wanted to check if my previous response addressed your question correctly. If there is anything I may have misunderstood, I would truly appreciate it if you could provide a bit more detail to help me better understand your needs.
Ginger 0 Reputation points

2026-10-03T17:21:22.4066667+00:00

thanks for looking into this.

AT&T / Yahoo mail.

No one receives entries from "Direct Replies To" I- not even the Send to person nor either of the Replies To addresses. Instead, get Sys Admin undeliverable es

It doesn't work at all.

MS Outlook for M 365 MSO version 2609
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Ginger 0 Reputation points

2026-10-04T05:22:51.2866667+00:00

No matter what mailbox I try to send to when using the Options/Send Replies To field, I get a System Admin undeliverable error: 550 Request failed; Mailbox unavailable. I have tested using all the email addresses I own with Microsoft/bellsouth/yahoo. These are email addresses I use frequently. Nothing works. This SEND REPLIES TO feature is NOT working! Please provide fix...
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This comment has been deleted due to a violation of our Code of Conduct. The comment was manually reported or identified through automated detection before action was taken. Please refer to our Code of Conduct for more information.
Hornblower409 16,580 Reputation points

2026-10-06T05:27:09.1566667+00:00

@Ginger said

No matter what mailbox I try to send to when using the Options/Send Replies To field, I get a System Admin undeliverable error: 550

I have just tested and it works OK for me.

Sending:

Receive and Reply

I have tested using all the email addresses I own with Microsoft/bellsouth/yahoo.

Assume you have already tried manually changing the "To" on the Reply to a know good address, but it still fails to deliver?
Ginger 0 Reputation points

2026-10-06T06:28:52.3833333+00:00

Yes. I followed all the same steps - on 2 different computers using only addresses I own. It fails every time. It used to work. No longer. Not sure if AT&T blocking or Yahoo (used by AT&T) or what is wrong.

Thank you for taking time to go through all the steps; wish it worked consistently for everyone.
Hornblower409 16,580 Reputation points

2026-10-06T06:49:15.8833333+00:00

?) Do I understand correctly, the problem is when you send the original? Not when you reply to it?

All I can suggest at this point are the The Usual Suspects (what you try when you really don't know what's wrong).

Office Outlook Repair
https://support.microsoft.com/en-us/office/lifecycle/repair-an-office-application

Outlook in Safe Mode
https://support.microsoft.com/en-us/office/open-outlook-in-safe-mode-f394c2ee-b2af-e97a-64ee-35cd24414811
Emma1-N 13,685 Reputation points Microsoft External Staff Moderator

2026-10-06T07:01:50.73+00:00
Hello Ginger,

Could you please share the complete 550 NDR (Non-Delivery Report) message, with any personal information removed? The exact wording can help identify which mail server is rejecting the message.

Also, as a quick test, please try sending the message with Outlook running in Safe Mode:

Press Windows + R

Type: outlook.exe/safe

Test the "Direct Replies To" feature again.
Ginger 0 Reputation points

2026-10-06T15:54:28.43+00:00

The email NEVER gets to anyone. I get Sys Admin undeliverable message: I removed email address in the below..

       Subject:     test

      Sent: 10/3/2026 11:02 PM

The following recipient(s) cannot be reached:

       '' on 10/3/2026 11:02 PM

            550 Request failed; Mailbox unavailable
Ginger 0 Reputation points

2026-10-06T16:22:48.6433333+00:00

I will try repair and safe modes tonight/tomorrow; thanks.
Hornblower409 16,580 Reputation points

2026-10-06T20:25:34.43+00:00

@Ginger

Just to be sure :

1 -- Can you send to that recipient if it does not have any "Direct Replies To" value? i.e. Just a plain send.

2 -- Can you send to that recipient if the "Direct Replies To" value is your own address? i.e. It has a "Direct Replies To" value, but it's the same as what a normal Reply would use.

3 -- Can you send to any other recipient (e.g. yourself) with a "Direct Replies To" value?
Emma1-N 13,685 Reputation points Microsoft External Staff Moderator

2026-10-07T06:37:35.48+00:00
Hello Ginger,

Run Outlook in Safe Mode (outlook.exe/safe) and test again.

If the issue persists, perform an Office Quick Repair:

Open Control Panel > Programs and Features

Select Microsoft 365 > Change

Choose Quick Repair

Let try it and let me know the result.
Ginger 0 Reputation points

2026-10-07T20:34:01.3266667+00:00

already tried; doesn't work at all - sys admin reply - no one at any address gets my email when use direct repines to
Hornblower409 16,580 Reputation points

2026-10-07T22:44:40.3866667+00:00
@Ginger said

already tried; doesn't work at all

If you would please, it might help to look at the "raw" email that is being sent. It's possible, that by adding a "Reply To:", it is causing Outlook to mess up the "To:" line.

Open one of the bad emails from your Sent Items folder and examine the email header.
https://support.microsoft.com/en-us/outlook/view-internet-message-headers-in-outlook

After all the gibberish, you should see a human readable section. A normal email header, with a Reply To, will have this kind of layout in that section:

From: Name <email>

Sender: {From email}

Reply-To: {Reply To email}

To: {Original To email list}

Subject: XXXXX

Has Outlook messed up the "To: " line? So it's not what you used when composing.
Does the "Reply-To: " address look correct?
Ginger 0 Reputation points

2026-10-08T04:57:16.9+00:00

I cannot reply because it never sends. I will add answers to your questions - will try to add next to my original post
Ginger 0 Reputation points

2026-10-08T05:02:25.5833333+00:00

I cannot reply because when I use the "Direct Replies To" field, the email NEVER gets to the "TO" address (which is a good address I own). Please note: I added a comment to my original post about the issue to hopefully answer other questions.
Hornblower409 16,580 Reputation points

2026-10-08T05:06:04.8766667+00:00

@Ginger said

I cannot reply because it never sends

Do I understand correctly? The original (the one you sent) is not in your Sent Items folder? That is where I need to you look at the "raw" message.
Hornblower409 16,580 Reputation points

2026-10-08T05:13:07.7766667+00:00

@Ginger

NIX NIX. My mistake. You can not View Message Headers for an item in the Sent Items folder. I will work up an alternative and advise.