Outlook 2016 sends email with a cryptic reply to address

I have an Office 365 account through which I have an email account on Outlook.com. I have installed MS Office 2016 on my computer, with the latest updates. When I use the Outlook 2016 program to send an email, the return address is no longer my *** Email address is removed for privacy ***. instead, it is a cryptic address like: *** Email address is removed for privacy ***.

If someone tries replying to my message, the reply is bounced back with this message:

A message that you sent could not be delivered to one or more of its recipients. This is a permanent error. The following address(es)

failed: 

*** Email address is removed for privacy ***:

SMTP error from remote server for RCPT TO command, host: mx3.hotmail.com (65.55.92.168) reason: 550 Requested action not taken: mailbox unavailable

I have set an alias as my reply to address and it overcomes this problem, but then the messages show "Sent from my personal email address in the name of *** Email address is removed for privacy ***," Which 1) doesn´t look professional, and 2) when I click reply, it still tries to reply to the cryptic address above.

How can I change either the account on outlook.com OR the account settings on Outlook 2016 so that sending messages shows the correct sending address and if someone clicks the reply button, it replies to the correct address, not the cryptic one?

BTW: when I have searched for this problem on the MS support and community forums, all I find are, "This question was answered at ...," which it was not. So please don´t point me to a solution that matches the search heading, but doesn´t actually tell me how to fix the problem.

Thanks

***Post moved by the moderator to the appropriate forum category.***

Hi,

To better assist you with this concern, kindly answer the following:

  • Any changes made prior to this concern?
  • What are the troubleshooting steps have you done so far?
  • Which version of Windows are you currently using?

In the meantime, we suggest that you remove and re-add your account in Outlook 2016. If it doesn't work, let's create a test account and add it to your Outlook 2016. Once done, try sending an email to any of your other email account and check if you will still experience the same problem. This test will let us isolate the problem if this is only happening on a specific account.

Let us know the result.

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I have the same exact issue, but even though outlook.com in a browser.    When an email goes out, it sends as from *** Email address is removed for privacy ***
I tried sending an email from a gmail account to the outlook_xxxxxxxxxxxxxx@

he response from the remote server was:

550 5.7.66 Requested action not taken: mailbox unavailable [BN3NAM04FT046.eop-NAM04.prod.]

Final-Recipient: rfc822; outlook_XXXXXXXXXXXXXX@
Action: failed
Status: 5.7.66
Remote-MTA: dns; outlook-com.olc.protection.. (104.47.46.33, the
 server for the domain outlook.com.)
Diagnostic-Code: smtp; 550 5.7.66 Requested action not taken: mailbox unavailable [BN3NAM04FT046.eop-NAM04.prod.]
Last-Attempt-Date: Wed, 20 Sep 2017 11:28:11 -0700 (PDT)


---------- Forwarded message ----------
From: ME <*** Email address is removed for privacy ***>
To: ME <*** Email address is removed for privacy ***>
Date: Wed, 20 Sep 2017 13:27:55 -0500
Subject: test to outlook cryptic address
outlook_XXXXXXXXXXXXXXXX@

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Please have a look at the Outlook.com email account appears as "outlook_[long series of letters and numbers]@outlook.com" in Outlook for Windows [WORKAROUND] section in the Outlook issues after connecting Outlook to Outlook.com portion of this article, it may be involved:

Fixes or workarounds for recent issues on Outlook.com

Hal Hostetler, CPBE
Broadcast Engineer/IT Pro
MVP-Outlook - WA7BGX
www.rolandschorr.com

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Last updated September 30, 2021 Views 854 Applies to: