Need help fixing Microsoft's bizarre organization of sent messages

Question

A few days ago, our organization switched our email accounts from a "regular" email server company to Microsoft.  This has wreaked havoc on the organization of sent emails for people on Mac.  Before the switch, sent messages were like they've been with every company I've used in the past -- one place for sent messages, with the name showing in the list being the person who the message was sent to.

With our switch to Microsoft, it has created a bizarre organization of sent messages.  It has put occasional and random messages in Sent Items, properly showing who they were sent to.  However, nearly all sent messages have instead been put into a subfolder of the Inbox, and worst of all, the name on all the messages in the list is the SENDER'S name, not who the message is being sent to, making the list useless.  This organization appears in Apple Mail, desktop Outlook for Mac, and even Outlook online.

In a meeting today with our Windows teammates, I discovered that Microsoft is not doing this to them.  THEY have normal Sent Items boxes, where all the sent mail is in one place and the list shows who the messages were sent to.

I have looked and looked on the web for a solution to this, but I am finding nothing.  This is a big deal because not being able to see who messages were sent to in my sent list destroys productivity.  How can we make Microsoft organize our sent messages in the normal way for those of us on Macs?

Answer 1

It turns out that this was related to something about the way the email was migrated from our previous email company to Microsoft, and the during the transition, both were operational.  It only affected Apple Mail users.  To make the sent messages go where they should (Sent Items), the previous vendor had to be completely removed from Apple Mail.

In all Apple Mail users, during the transition, sent messages were going to a subfolder of Exchange's inbox.  In Big Sur Apple Mail, the sent-to names were showing in that list, as one would expect in a sent mail list.  In Apple Mail versions before Big Sur, the sender's names were showing in the list, making the list of no practical value.  At any rate, once the previous vendor email account was deleted from Apple Mail, Exchange started putting messages in Sent Items, where they belong, with the sent-to name showing in the list.

Answer 2

Hello SA Principal,

Thanks for update and sorry for late response. Sure, you can share your details via Private Message. Once we received your details, we will check and assist you further.

Regards,

Ankita Vaidya

Answer 3

Thank you for your reply.

1. In Rules, it says, "You haven't created any rules yet."
2. "...switched our email accounts..."  Previously, we have used IMAP accounts from providers such as GoDaddy, InMotion, MacHighway, etc.
3. License: Office 365 A3 for faculty
4. Yes, other Mac users are having the same issue. Windows users are not.
5. To show you what I'm talking about by posting an image, it would have sender's names.  I don't want to put that in a public place. I can provide a screenshot privately if you let me know where to submit it.

Answer 4

Hello SA Principal,

Thanks for your post in this community.

Based on your post, seems the sent emails are listed in Inbox, so would like to confirm is there any Inbox rule is set on your account? You can check this by open Outlook from mac or Outlook web app, then go to the Tools/settings menu and select Rules to view it. If any unknown rule found, please kindly disable it and check if it makes any difference.

Further to narrow down the issue, we have to collect some information from your end, so request you to please kindly share with us.

• Detail information about “switched our email accounts from a "regular" email server company to Microsoft.”
• Which Microsoft365 subscription is assigned to you.
• Detail screenshot of the issue.
• Does the other users in your organization are facing this issue?

Once we received the above requested information, we will check and assist you further. Your kind understanding and co-operation will be highly appreciated.

Thanks you so much for your precious time. Stay safe and healthy.

Regards,

Ankita Vaidya