Share via

Reply with the same alias email address that email was received on

C. Meyer 0 Reputation points
2025-04-30T09:03:32.3+00:00

Hello support team,

I am opening a new ticket here, since the environment I am working on is Hybrid. Please check the following topic that I previously opened on the Outlook Community: https://answers.microsoft.com/en-us/outlook_com/forum/outlk_win-outtop_new-outsub_ofb/reply-with-the-same-alias-email-address-that-email/5e4b3bbf-d0bb-4373-8849-58b28b320568?messageId=df13fbf3-5257-41d1-abf6-7697efb33130

Here is my use case:
There are two aliases set on my Outlook mailbox: Alias A (related to topic A) and Alias B (related to topic B). I would like to be able to reply with the same alias email address that the email was received on.

With this mailbox, I am able to receive emails sent either to Alias A and to Alias B, and to organize the emails using rules. I would like to be able to answer by sending emails from Alias A or from Alias B depending on the topic.

When trying to answer from Alias B, I am receiving the following error message: "This message could not be sent. You do not have the permission to send the message on behalf of the specified user. ".

How to change the configuration of Alias B in order to be able to send emails from this address?

Please note that I am using the New Outlook for Windows, on a hybrid setup with enterprise licence.

Thank you,

Best regards,

C. Meyer

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
5,850 questions
0 comments

1 answer

Sort by: Most helpful
Most helpful Newest Oldest
  1. Hien-L 1,910 Reputation points Microsoft External Staff
    2025-05-01T05:51:59.77+00:00

    Hi C. Meyer,

    To resolve the issue where you cannot send emails from Alias B in your hybrid Exchange setup, follow these steps:

    1. Verify Alias Configuration in Exchange
    • Admin Action: Ensure Alias B is correctly added as a secondary SMTP address on your mailbox. This is typically done in the Exchange Admin Center (EAC) or via PowerShell:

    Set-Mailbox "YourPrimaryEmail" -EmailAddresses @{Add="******@domain.com"}

    In a hybrid setup, confirm synchronization between on-premises Exchange and Exchange Online (use Azure AD Connect).

    1. Grant "Send As" Permissions
    • Admin Action: Explicitly grant "Send As" permissions for Alias B (even though it’s your own alias). This can be done via Exchange Admin Center or PowerShell:

    Add-RecipientPermission "******@domain.com" -Trustee "YourUserAccount" -AccessRights SendAs

    • Wait for permissions to sync in hybrid environments (may take time or require manual sync).
    1. Configure Outlook to Use Alias B
    • User Action:
    1. In New Outlook for Windows, go to Settings (gear icon) > Accounts.
    2. Select your account > Email aliases.
    3. Ensure Alias B is listed. If not, manually add it under "Send from another address".
    4. When replying, click the From field and select Alias B.

    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

    Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

    0 comments

Your answer

Answers can be marked as Accepted Answers by the question author, which helps users to know the answer solved the author's problem.