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felixtech's avatar
felixtech
Copper Contributor
Jul 04, 2023

Proxy addresses broken after enabling Azure AD Connect

Hi everyone,   we were using Exchange Online with built-in authentication. Each user has 2 SMTP e-mail address types configured as well as multiple shared mailboxes open. When creating a new e-mail...
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Dan_Snape's avatar
Dan_Snape
Bronze Contributor
Jul 05, 2023
Are the mailboxes located in Exchange Online? I believe the functionality to select the sending SMTP alias that is used is still in preview (https://techcommunity.microsoft.com/t5/exchange-team-blog/sending-from-email-aliases-public-preview/ba-p/3070501).
With delegate access, are the two mailboxes located in the same location (both on-prem or both in EXO). I always recommend having the delegates in the same location, even though it is supposed to work when they are not.
  • felixtech's avatar
    felixtech
    Copper Contributor
    Jul 05, 2023

    All mailboxes are EXO only. The whole system started as EXO only - there has never been an On-Prem install.
    The basic feature to SendAs and SendOnBehalf has worked for me forever and if that wouldn't work that would completely invalidate mailbox delegations.
    The menu point as described in the blog article doesn't even exist for me anymore. Since activating AD sync all options for this have disappeared even though they existed forever before. Also disabling AD sync didn't revert the breakdown.

     

    Edit:

    After a further test I found out that I can SendAs a shared mailbox by manually typing the From address in Outlook Desktop (dropdown is missing). But I cannot SendOnBehalf a shared mailbox and I cannot send as my second proxy address.

    • Dan_Snape's avatar
      Dan_Snape
      Bronze Contributor
      Jul 10, 2023
      Sorry, your initial post didn't indicate you were using SendAs and SendOnBehalf. I had though you were just trying to send as an alias SMTP address.
      Do you see the From field at all? You can turn it on by opening a new message and going to Options -> From
      Is this working from Outlook on the Web?
      • felixtech's avatar
        felixtech
        Copper Contributor
        Jul 10, 2023

        Dan_SnapeWhat I expect is that I click New E-Mail and then click the From dropdown and then I should be able to select my own proxy addresses as well as the addresses of the shared mailboxes I'm allowed to SendAs and/or SendOnBehalf.

        Per default I do not see the From field. When I manually enable it in the settings then I see only my own primary address to choose from. My proxy address and the shared mailboxes are missing completely.

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