I have lost emails after reverting to Legacy Outlook on my Mac

Question

I have lost emails after reverting to Legacy Outlook on my Mac

Jon Strong 20

I migrated to New Outlook on my Mac not realising I would loose the rules. I have reverted back to legacy Outlook on my Mac because I need the rules.

I seem to have lost all my sent items and my historic email prior to the original migration including any emails in folders. The folders have come over.

How to I recover all my emails?

The only .olm file i see is from 2020 and was last modified then so I don't believe the emails I sent yesterday will be in in that.

This is an appallingly bad conversion reversion process. It is not minimum viable product level in my view.

Regards,

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Answer 1

Victor1-V 13,025 Microsoft External Staff Moderator

Hello Jon Strong,

I understand how worrying it is to see Sent Items and older folder emails missing after switching back to Legacy Outlook for Mac. Please note that this is a user-to-user forum, so contributors here cannot access or restore mailbox data directly.

Please first sign in through webmail, such as Outlook.com or your email provider’s webmail, and check whether the missing emails are still there. If they appear online, the messages are still on the server, and Legacy Outlook may only need time to sync, or the account may need to be added again.

If the missing emails were stored under “On My Computer,” they may only exist in the local Outlook profile or a local backup. In Legacy Outlook, go to Outlook > Settings > General, then clear Hide On My Computer folders and check those folders again.

If the only .olm file available is from 2020, it would not contain emails sent yesterday unless a newer export was created. In that case, please check whether you have a Time Machine backup from before the switch or reversion. You may also temporarily switch back to the new Outlook view to see whether the missing items are still visible there.

If they are still missing from webmail, On My Computer, and there is no recent .olm or Time Machine backup, please contact Outlook for Mac support from Help > Contact Support for account/profile-specific assistance. Reference: Contact support within Outlook for Mac | Microsoft Support.

You can also contact Microsoft Support from the contact page with below steps:

Visit the Microsoft Support contact page: Contact - Microsoft Support
In the search bar provided on the page, type "Outlook issue" and press Enter.
Click on the "Get Help" button that appears.
Scroll down the page until you see and click on the "Contact Support" option.
When prompted to select your product or service, choose "Other Products".
For the category, choose "Outlook".
Look for and click on "Chat with a support agent in your web browser".
Confirm your personal email when prompted - this is the email Microsoft will use to communicate with you during and after the support session.
Explain your situation clearly: Be concise but provide all the relevant details.

I hope this helps you confirm whether the emails are still on the server or recoverable only from the local Outlook profile or backup.

Jon Strong 20 Reputation points

2026-06-23T10:37:39.3633333+00:00

The solution that worked for me, partially, is to revert back to New Outlook. There seem to be some gaps in the conversion / reversion processes. Firstly, the conversion process to New Outlook doesn't make clear that Rules will be lost. Second the reversion process doesn't make clear that a .olm backup of one's entire mailbox needs to be taken for import back into legacy.

I had two different experiences with Microsoft Support. The webchat experience was appalling. My Net Promoter Score (NPS) rating would have been 1. The agent just got to a point in the script where it said the problem was with my webmail provider. I thought I would try the phone contact. That was an experience I'd give a 9 for my NPS rating. The phone agent's script was obviously different or she was listening and applying her intelligence and knowledge to the problem. She made the recommendation to revert to New Outlook. She had the patience to wait to confirm that it had worked.

I give the solution as partial for me as I do not trust the process of taking a .olm backup, reverting to Legacy and then importing the .olm. It seems better to me to find an email client with rules and then archive my MS Outlook mailbox.

I also need a new hard drive so that my Time Machine backups function! Apparently my Airport Time Capsule no longer works with the latest MacOS.
Victor1-V 13,025 Reputation points Microsoft External Staff Moderator

2026-06-23T14:48:31.0466667+00:00

Thank you for sharing the update. I am glad to hear that reverting to New Outlook helped restore access at least partially.

Based on what you described, keeping the mailbox in the Outlook version where the messages are currently visible is the safest approach for now. I also agree that importing an older .olm file would not be useful for recent emails, and any further export, import, or profile change should only be done after creating a current backup of the Outlook data and checking whether the messages are visible in webmail or only in the local Outlook profile.

For the rules, they may need to be recreated in the Outlook version you decide to continue using. If you still need account or profile-specific recovery help, the best route is to continue with Outlook for Mac in-app support through Help > Contact Support, since support can review Outlook logs and the local client behavior more closely.

I hope your update helps other users understand the backup and New Outlook/Legacy Outlook transition risks more clearly.
Jon Strong 20 Reputation points

2026-06-23T15:33:54.4666667+00:00

Thanks for your help Victor1-V
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Victor1-V 13,025 Reputation points Microsoft External Staff Moderator

2026-06-24T06:17:50.2333333+00:00

You are welcome, Jon!