Deleting Drafts deletes emails from Sent folder

Question

Deleting Drafts deletes emails from Sent folder

Lizzie J 0

When I send an email, the message first moves to Drafts (as expected during composition). After the email is sent, a copy remains in the Drafts folder as a leftover. When I delete this leftover draft copy, the corresponding email in Sent Items is also deleted — permanently. It does not appear in Deleted Items either. This is proving problematic as I am then unable to locate emails I am certain I sent for uploading to a service user's NHS care record.

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Answer 1

Michelle Nguyen 1,015 Independent Advisor

Hi @Lizzie J

Based on your description, I understand that after sending an email, a leftover copy remains in your Drafts folder, and deleting that draft also permanently removes the message from Sent Items, which is causing difficulty locating emails you need for a service user’s NHS care record.

To help me narrow down the cause, could you please provide the following information?

What type of email account are you using? (Microsoft 365/Exchange, Outlook.com, Gmail, or another provider added as IMAP/POP). You can check this via File > Account Settings > Account Settings — the Type column will show Exchange, IMAP, or POP. This is important because this behavior most often occurs with IMAP accounts, where the “draft” and “sent” copies can actually be the same underlying message displayed in two folders.
Which version of Outlook are you using? Classic Outlook for Windows, new Outlook, Outlook for Mac, or Outlook on the web and if possible, the version/build number (File > Office Account).
Does this happen with every email you send, or only occasionally?

In the meantime, I would suggest the following:

Please avoid deleting the leftover drafts for now, since doing so is removing your sent record as well.

Check whether the sent copies still exist on the server: Sign in to your mailbox via the web (Outlook on the web at outlook.office.com, or Gmail on the web if it is a Gmail account) and check the Sent folder there. In many cases, the sent message still exists server-side, and the issue is only how Outlook desktop is displaying or syncing it. If the messages are visible on the web, you can recover them from there for the care record.

If the messages are intact on the server, the issue likely lies with the local cache or profile. In that case, you can remove and re-add the email account, or create a new Outlook profile (Control Panel > Mail > Show Profiles > Add), as a corrupted local cache is a common cause of duplicated messages.

Once I have the details above, I can provide more targeted steps to resolve this.

Look forward to your reply.

Lizzie J 0 Reputation points

2026-08-13T14:54:52.3933333+00:00
What type of email account are you using? Microsoft 365

Which version of Outlook are you using? New Outlook

Does this happen with every email you send, or only occasionally? It seems to be happening with every email from a shared mailbox this afternoon but not from my individual email account having just tested that.

I signed into my mailbox via the web and the messages don't exist server side.
Michelle Nguyen 1,015 Reputation points Independent Advisor

2026-08-14T16:39:19.1733333+00:00
Hi @Lizzie J

Because the account is Microsoft 365/Exchange, the issue occurs only when sending from a shared mailbox, and the messages are not present in Outlook on the web/server side, I would not recommend treating this as a local Outlook cache/profile problem yet.

The important clue is that deleting the leftover Draft causes the corresponding Sent message to disappear permanently. That suggests the Draft and Sent copy may be linked to the same underlying Exchange item, or that the shared mailbox's send/save behavior is creating an incorrect item relationship.

Please check more informations

Confirm where the sent item is actually being saved

Send a test message from the shared mailbox.

Check the shared mailbox's Sent Items in Outlook on the web.

Also check the user's personal Sent Items.

Check whether the message appears in the shared mailbox's Drafts in Outlook on the web.

Do not delete the Draft during this test.

Check the shared mailbox's Sent Items configuration For Microsoft 365 shared mailboxes, an important setting is whether messages sent as or on behalf of the shared mailbox are saved in the shared mailbox's Sent Items folder. An administrator can check the shared mailbox configuration with Exchange Online PowerShell. The relevant settings are:

MessageCopyForSentAsEnabled

MessageCopyForSendOnBehalfEnabled

Ideally, for a shared mailbox where staff need an auditable sent record, these should be enabled so sent messages are retained in the shared mailbox's Sent Items.

Test Outlook on the web rather than New Outlook Send a test message directly from Outlook on the web using the shared mailbox. If the problem occurs there too—i.e. a Draft remains and deleting it removes the Sent item—that would strongly point away from the New Outlook client and toward the mailbox/Exchange configuration.

Check permissions on the shared mailbox In particular, verify the user has the expected:

Send As or Send on Behalf permission

Full Access permission

It is also worth checking whether the shared mailbox was recently changed, migrated, had permissions modified, or had another mail client/application connected to it.

Please keep me updated.
Michelle Nguyen 1,015 Reputation points Independent Advisor

2026-08-17T05:18:59.23+00:00

Hi @Lizzie J

Is there any update from you?

If yes, please feel free to let me know
Lizzie J 0 Reputation points

2026-08-18T13:06:51.6166667+00:00
Confirm where the sent item is actually being saved

Send a test message from the shared mailbox.

Check the shared mailbox's Sent Items in Outlook on the web. The item goes into shared mailbox Sent Items in Outlook on the web and Outlook desktop version.

Also check the user's personal Sent Items. The item is not in personal Sent Items in Outlook on the web or Outlook desktop version.

Check whether the message appears in the shared mailbox's Drafts in Outlook on the web. The item does not appear in shared mailbox Drafts in Outlook on the web.

Do not delete the Draft during this test.

Check the shared mailbox's Sent Items configuration For Microsoft 365 shared mailboxes, an important setting is whether messages sent as or on behalf of the shared mailbox are saved in the shared mailbox's Sent Items folder. An administrator can check the shared mailbox configuration with Exchange Online PowerShell. The relevant settings are:

MessageCopyForSentAsEnabled

MessageCopyForSendOnBehalfEnabled
I don't have access as I am not an administrator. **
**4. Test Outlook on the web rather than New Outlook Send a test message directly from Outlook on the web using the shared mailbox. If the problem occurs there too—i.e. a Draft remains and deleting it removes the Sent item—that would strongly point away from the New Outlook client and toward the mailbox/Exchange configuration. Problem does not occur when message sent from Outlook on the web.
Lizzie J 0 Reputation points

2026-08-18T13:08:19.98+00:00

From some personal testing I also realised that closing the Outlook desktop app and reopening removes the Draft but the original email is then still in Sent items as you would expect and want.
Lizzie J 0 Reputation points

2026-08-18T13:09:18.3466667+00:00

And when the problem happens, the original email does end up in Deleted items, but in my personal Deleted items and not the shared mailbox Deleted items.
Michelle Nguyen 1,015 Reputation points Independent Advisor

2026-08-19T02:45:58.32+00:00

Hi @Lizzie J

Thank you for the update. In that case, could you please help me try reinstalling the Outlook app and see if the issue persists? Since the problem does not occur in Outlook on the web, it seems more likely to be related to the desktop application.

Please let me know if you find any additional information or notice any changes after the reinstall. Thank you!
Michelle Nguyen 1,015 Reputation points Independent Advisor

2026-08-20T10:23:00.9833333+00:00

Hi @Lizzie J

Is there any update from you?

If yes, please feel free to let me know