This is Outlook Deleted Items recovery at its simplest, with no server step and no extra software. Some accounts show this folder as Trash instead of Deleted Items. Note which name yours uses. It matters in the section on a missing button.

To find deleted items in Outlook when the folder holds hundreds of messages, type the sender's name or a word from the subject into search box while Deleted Items is selected. You can also drag the message straight onto Inbox in the folder pane. In new Outlook, tick the box next to the email and click Move on the Home tab, or right-click it and choose Restore. Check Junk Email too if a message never showed up at all.
A whole folder you deleted by mistake usually lands inside Deleted Items as a subfolder. Expand Deleted Items and drag it back into your folder list. Every message inside comes back with it.

Undo it with Ctrl+Z if you deleted it a moment ago:

The fastest Outlook undelete email shortcut is Ctrl+Z. Press it right after the delete and the email returns to the folder it came from. This only works within the same Outlook session. Close Outlook and the undo history is gone.

Which Outlook account do you have: POP, IMAP or Exchange?

Check the account type in classic Outlook:

Go to File > Account Settings > Account Settings and open the Email tab. The Type column shows POP/SMTP, IMAP/SMTP or Microsoft Exchange for each mailbox. A work or school address on Microsoft 365 shows as Exchange. An @outlook.com or @hotmail.com address also uses the server route.

What the type means for you:

• Exchange or Microsoft 365: deleted mail moves to the Recoverable Items folder on the server, and Recover Deleted Items From Server brings it back.
• Outlook.com: the same server folder, opened from the web or new Outlook.
• IMAP (Gmail, Yahoo, many hosting plans): Outlook mirrors the server, so emptying Deleted Items usually deletes the server copy as well.
• POP: mail was downloaded into a .pst on your PC. The server copy may be long gone, and the .pst is where the deleted records still sit.

Once Deleted Items is emptied, Outlook cannot get the mail back from a POP account. The .pst file on disk may still contain it.

Microsoft's own walkthrough for recovering deleted items in Outlook for Windows covers the same dialog. The same window also lets you purge items for good, so read the option name twice before you click OK.

How to restore deleted emails in Outlook on the web and in new Outlook

In Outlook on the web, look for the link at the top of the Deleted Items list, above the messages. In the new Outlook app, after you tick the emails, select Restore on the Home ribbon and then Go back to deleted items to see them in the folder again. From there, move them to Inbox.

Microsoft notes that mobile browsers cannot open the Recoverable Items folder, so do this step from a PC or Mac. On Outlook.com, under Settings > Message handling, the option "Empty my deleted items folder" clears Deleted Items every time you sign out. Turn it off if you want a few days of grace before mail moves to the server folder.

How long can you recover permanently deleted emails?

14 days

Source

"Permanently deleted" means you emptied Deleted Items or pressed Shift+Delete on a message anywhere in the mailbox. Both send the email to the Deletions part of the Recoverable Items folder in Exchange Online, and the clock starts then, not when you first deleted it.

This route to deleted email recovery in Outlook fits the POP and IMAP cases where the server has nothing left and you still have the data file. Deep scan has to be chosen by hand. The default Automatic mode opens a healthy file the way Outlook does and leaves deleted mail hidden, because it only goes deeper when it sees damage.

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That result comes from a test file with little written after the deletion. A mailbox that kept receiving mail for weeks gives back less, and bodies go first. Outlook reuses body blocks early, so many recovered emails arrive with headers and a [partial] tag. For a client asking "who sent what, and when", that can be enough to find the thread again.

Run Deep scan on a copy of the file:

Open the copy of your .pst or .ost in PST Repair Tool. Outlook does not need to be installed on the PC. In the scan depth list, pick Deep scan instead of Automatic or Quick only, and start the scan. Before it begins, the tool checks that the target drive has room for about three times the file size.

When the scan ends, browse the folders in the preview and open the messages you were after. Save them as a new PST, or as MSG, EML, MBOX, PDF or HTML files. The report counts messages found and written, and the ones tagged [partial]. What could not be recovered is listed too. The trial shows every recovered message in the preview, so you can see what survived before you buy. Saving the results needs a license.

The wizard asks how to handle duplicates and where to put the items. Pick a separate folder rather than Import items into the current folder, so a three-month-old backup does not mix with today's Inbox. Microsoft's guide to importing email from an Outlook .pst file lists every screen of the wizard.

If you need only a few emails, open the backup as a second data file. Classic Outlook does it through File > Open & Export > Open Outlook Data File, and new Outlook through the Add file button in its data file settings, which works only with classic Outlook installed and a Microsoft 365 subscription. The backup shows up as its own folder tree, and you drag back only what you lost. No Outlook on the machine? You can still open a PST file without Outlook and read it with a free PST viewer.

If File History or a similar tool covers the folder where the .pst lives, right-click the file in File Explorer and check Properties > Previous Versions for an older copy. Restore it to a different folder, never over the live file.

How to recover sent emails in Outlook when they go missing

Before you assume a delete, confirm Outlook saves sent mail at all. In classic Outlook, go to File > Options > Mail and check that "Save copies of messages in the Sent Items folder" is ticked. Then search with the scope set to all mailboxes, since IMAP profiles sometimes file sent mail under a second folder with similar name.

A bulk delete on IMAP can remove the server copy after Deleted Items is emptied. On Microsoft's Q&A forum, the answer to exactly this case was short. The messages were deleted from the IMAP server and will not be recoverable there. What remains is the local cache file on the PC, if Outlook has not overwritten it yet, or a backup.

How to stop losing Outlook emails next time

Schedule a reminder to back up Outlook emails to a .pst and keep the last few copies on a different drive. Ask your IT team how long your mailbox keeps deleted items, and get the number in writing. Stop emptying Deleted Items on autopilot and let it hold a few weeks of mail.

If you are on POP, treat your .pst as the only copy of your mail. A failing drive takes the deleted emails and everything else with it.

Sources

• Change how long permanently deleted items are kept (Microsoft Learn)
• Recover deleted emails in Outlook (IONOS Digital Guide)