Recovering Deleted Emails Through Apple Mail

Question

In apple mail I have set a rule incorrectly and it's deleted all my emails. They seem to be permanently deleted - is there a way I can recover them through outlook?

Answer 1

Have you tried the instruction here? https://support.microsoft.com/en-us/office/recover-and-restore-deleted-items-in-outlook-49e81f3c-c8f4-4426-a0b9-c0fd751d48ce#picktab=web

It must be done on the web in order to find the option referenced.

In outlook.com via web browser, go to Deleted items, see if you still have the "recover deleted items from this folder" option to recover. If not, then it is not recoverable beyond this point.

However, if this is a work/school account, it might be recoverable, depending on each organization's retention policy. Reach out to your organization's IT support team, they would know what the retention policy is for your organization and can recover for you if it is still within the defined retention period.

Answer 2

If Apple Mail has permanently deleted the messages from the server (for example, emptied Trash or purged an IMAP folder), Outlook cannot recover them independently. Recovery depends entirely on whether the messages still exist in a recoverable location on the mail server or in a local data file.

Use these approaches, depending on the account type and server behavior:

1. If the account is Exchange/Outlook.com and supports “Recoverable Items”
   • Sign in to Outlook on the web (or use classic Outlook on Windows if available) with the same account Apple Mail uses.
   • In Outlook on the web:
     1. Open the Deleted Items folder.
     2. At the top of the message list, select Recover items deleted from this folder.
     3. Select the items to recover and choose Restore.
        • Restored messages go back to their original folders when possible; otherwise they go to Inbox, Calendar, Contacts, or Tasks as appropriate.
   • In classic Outlook (Windows) with an Exchange/Outlook.com account:
     1. Go to the Deleted Items folder.
     2. On the Home tab, select Recover Deleted Items From Server.
     3. Select the items and choose Restore Selected Items, then OK.
   If the messages are not present in the Recoverable Items view, they have likely been permanently removed and cannot be restored by Outlook.
2. If the account is IMAP (e.g., Gmail, ISP mail)
   • Some IMAP servers keep deleted items in a Trash/Deleted folder for a retention period. Sign in to the provider’s webmail and check Trash/Deleted/Archive folders.
   • If the server has already purged them, Outlook cannot recover them.
3. If there is an Outlook data file backup (.pst)
   • If Outlook was previously used with this account and a .pst backup exists (for example, from another computer or older setup), open it in Outlook and recover mail from there.
   • Without such a backup, Outlook for Mac cannot reconstruct messages that the server and clients have permanently deleted.

If none of the above locations (Deleted Items, Recoverable Items, server Trash, or a backup .pst) contain the messages, they are considered permanently deleted and are not recoverable through Outlook.

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References:

• Recover and restore deleted items in Outlook
• Recover email that's been removed from your Deleted Items folder
• Recover an item that's no longer in your Deleted Items folder in classic Outlook
• Restore deleted messages when using an IMAP account