I can't seem to delete old or new emails in Outlook.

First reconnect classic Outlook to the mail server and test deletion in webmail; this determines whether the problem is limited to the Windows application or exists in the mailbox itself.

1. Check Outlook’s connection

1. Look at the status bar at the bottom of Outlook.
2. If it says Working Offline, select Send/Receive > Work Offline once. The button should no longer be highlighted and the offline status should disappear.
3. If it says Disconnected, sign in to the account through its webmail site and try deleting one message there.

If deletion works in webmail, the mailbox is functioning and the issue is local to classic Outlook. If it also fails in webmail, contact the email provider because client repairs will not correct a server-side mailbox problem. Microsoft notes that offline or conflicting client/server actions can also cause deleted messages to reappear after synchronization.^1^

2. Test without Outlook add-ins

If webmail works:

1. Close Outlook.
2. Press Windows key + R.
3. Enter outlook.exe /safe, then select OK.
4. Open the normal mail folder and try deleting a message.

If deletion works in safe mode, disable the add-ins:

1. Select File > Options > Add-ins.
2. Beside Manage, select COM Add-ins > Go.
3. Record which add-ins are enabled, then clear their check boxes—do not select Remove.
4. Restart Outlook normally.
5. Re-enable the add-ins individually, restarting Outlook after each one, until the problem returns.^2^

3. Test a new Outlook profile

If safe mode makes no difference, create a fresh profile:

1. Close Outlook.
2. Hold Shift while starting Outlook.
3. Select Options > New.
4. Enter a profile name, select OK, and add the email account.
5. Open Outlook with the new profile and test deletion.

Alternatively, press Windows key + R, enter Outlook.exe /profiles, and create the profile from there. If deletion works in the new profile, the original profile is damaged; continue using the new one after confirming that all required accounts and locally stored data are available.^3^

4. Repair the Outlook data file

Use this fallback if the new profile does not resolve the issue, particularly for a POP account or locally stored .pst file.

1. In Outlook, select File > Account Settings > Account Settings > Data Files and note the data-file location.
2. Close Outlook.
3. Back up the data file before repairing it.
4. Run SCANPST.EXE.
5. Select Browse, choose the affected .pst file, and select Start.
6. If errors are found, select Repair, then reopen Outlook and test deletion.

For an Exchange account, Outlook uses an offline .ost copy that can be recreated from the server. Confirm that the mailbox is fully synchronized before removing or recreating any local data file. The Inbox Repair Tool examines only the local Outlook data file, not the server mailbox.^4^

If Outlook displays a specific error—especially “You don’t have permission to perform this operation”—or deletion fails only in one folder, include that exact error, the account type (Microsoft 365/Exchange, Outlook.com, Gmail/IMAP, or POP), and whether webmail deletion succeeds. Those details determine whether folder permissions, synchronization, or local data repair applies.

References

1. [Classic Outlook](https://support.microsoft.com/outlook/getstarted/how-to-work-offline-in-outlook-for-windows#tips-for-reconnecting-to-classic-outlook)
2. [Classic Outlook](https://support.microsoft.com/outlook/getstarted/outlook-for-windows-not-responding-hangs-freezes-or-stops-working)
3. Create a profile in classic Outlook for Windows
4. Repair Outlook Data Files (.pst and .ost) | Microsoft Support