Outlook for Mac and Web is deleting emails I send to myself, and will not allow me to delete any emails myself

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Outlook for Mac and Web is deleting emails I send to myself, and will not allow me to delete any emails myself

Jay Goldman 20

Outlook for Mac and Web is (1) deleting emails I send to myself, (2) will not allow me to delete any emails myself, and (3) will not allow me to send emails from my Outlook account.

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Answer 1

Hi Jay Goldman,

Thank you for reaching out to us. Below is a detailed guide to help you resolve the three issues you're currently experiencing with Outlook on both Mac and Web:

Emails Sent to Yourself Are Being Deleted

Possible Causes:

The “Ignore Conversation” feature may be enabled.
Your email address might be blocked or marked as junk.
A rule or add-in may be automatically deleting your messages.

Steps to Resolve:

Go to the Deleted Items folder, select the affected email, and click “Stop Ignoring Conversation.”
In Outlook Web > Settings > Mail > Junk Email, check and remove your address from the blocked senders list.
Review your mailbox rules and disable any that may be deleting or moving your self-sent emails.

Unable to Delete Emails

Possible Causes:

Your mailbox may be under a Litigation Hold or Retention Hold.
The Recoverable Items folder may be full.
Your mailbox may have reached its storage quota.
There may be a sync issue with Outlook for Mac.

Steps to Resolve:

Ask your IT admin to check if your mailbox is under any hold and remove it if not needed.
In Outlook Web, go to Deleted Items > Recover items deleted from this folder, select all, and click Purge.
Check your mailbox storage and delete or archive emails to free up space.
If using Outlook for Mac, try clearing the cache or switching to the “Classic Outlook” view.

Unable to Send Emails

Possible Causes:

Your mailbox may be full.
Your account may be temporarily blocked from sending due to spam protection.
There may be a service outage.
The Outlook app may be experiencing a client-side issue.

Steps to Resolve:

Complete the cleanup steps from Issue 2 to free up space.
Try sending a simple test email to another address.
Log in to Outlook Web and check for any alerts or prompts to verify your identity.
If sending still fails, try using another email client or device.
If using manual POP/IMAP settings, verify your SMTP configuration.

Additional Tips

Regularly monitor your mailbox quota and use archiving features if available.
Avoid creating rules that filter your own messages.
Keep Outlook updated to the latest version.
Use Outlook Web to verify whether issues are client-specific or server-related.

If you need further assistance while following these steps, please don’t hesitate to reply to this email. We’re here to help.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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Answer 2

Jay Goldman 20

I have a 365 account for personal use, so there is no Admin or IT department, just me. I have two outlook.com accounts, and these problems are with the primary account, not the secondary, which is working perfectly.

I have removed and reinstated the primary account, and have reset it as well.

These problems no longer occur on my iPhone, MacBook Air, iPad or on the web. However, they are still present when I use Outlook on my MacBook Pro.

This means that the problem of emails I send to myself being deleted has been resolved, and I can delete emails as long as I do it on the web, iPad or iPhone. I cannot delete emails in my primary account with the Outlook app for Mac.

On that note, there are no Litigation or Retention Holds that I am aware of. I am retired and am not involved in any litigation whatsoever.

I had deleted all Rules before I reached out for help, so I don’t think that can be the problem.

‘Ignore Conversation’ is not activated anywhere in my account.

I have deleted / purged everything in the Recoverable Items folder .

I’m using less than 1% of my storage.

Drafts I create in the Outlook for Mac app do not appear on other devices.

The remaining problems (Can’t send an email, can’t delete an email) are now occurring only in my primary account on my Outlook for Mac app on my MacBook Pro.

Ryan-N 3,015 Reputation points Microsoft External Staff Moderator

2025-07-18T20:22:09.7566667+00:00
Hi Jay Goldman,

Thank you for your detailed update.

Based on your description, the remaining issues now appear only on the Outlook for Mac app on your MacBook Pro, and only with your primary Outlook account. Since everything works fine on your iPhone, iPad, MacBook Air, and via Outlook Web, this strongly suggests that the issue is specific to the Outlook client on your MacBook Pro, not your account or Microsoft servers.

Here are a few targeted steps to help resolve this:

Refresh Your Outlook Profile on Mac

It’s possible that the Outlook profile on your MacBook Pro is corrupted. Please try resetting it:

Quit Outlook completely.

Open Finder > press Command + Shift + G, and enter:

~/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles/

Locate the profile folder (usually named “Main Profile”).

Back it up, then delete it.

Restart Outlook and re-add your primary account.

Fully Uninstall and Reinstall Outlook on Your MacBook Pro

Reinstalling Outlook can help resolve persistent client-side issues.

Steps:

Quit Outlook.

In Finder, delete the following folders:

~/Library/Containers/com.microsoft.Outlook

~/Library/Group Containers/UBF8T346G9.Office

Reinstall Outlook from the Microsoft 365 website or the App Store.

Add your primary Outlook account again.

Try Using a New macOS User Account

This step helps rule out any conflicts within your current Mac user profile:

Go to System Settings > Users & Groups and create a new user account.

Log in to the new user account.

Install Outlook and set up your primary account to test sending and deleting emails.

Test Draft Sync and Email Functionality

After completing the steps above, try the following:

Create a new draft in Outlook for Mac and check if it syncs to your other devices.

Try sending a test email to yourself or another address.

Attempt to delete an email and confirm whether it reflects across devices.

If the issue persists after trying these steps, feel free to reach out and I’ll be happy to continue helping. We’re committed to resolving this for you.

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Answer 3

Jay Goldman 20

Hi, and thanks so much for all the help, that was brilliant! So, refreshing my Outlook Profile on my Mac seems to have resolved all the issues I've been dealing with. However, there is a new problem that may have been caused by all these changes: on my iPad and iPhone, there is an important folder that appears to be empty on these devices, whereas all the sub-folders and files appear as they should in Outlook on my Mac and on the web (outlook.com).

Ryan-N 3,015 Reputation points Microsoft External Staff Moderator

2025-07-21T18:52:02.1566667+00:00
Hi Jay Goldman,

Thank you again for your feedback, I’m glad to hear that refreshing your Outlook profile on Mac resolved the previous issues. Regarding the new problem with an important folder appearing empty on your iPad and iPhone, here are the detailed steps to help you resolve it:

Update the Outlook App

Open the App Store on your device.

Search for the Outlook app and make sure it’s updated to the latest version.

Use the “Reset Account” Feature

Open the Outlook app.

Tap your profile icon (top left), then go to Settings (gear icon).

Select the email account that’s experiencing the issue.

Scroll down and tap Reset Account.

Confirm the reset. This will clear the local cache and re-sync your mailbox from the server.

Remove and Re-add the Account (if needed)

If the issue persists after resetting:

Go to Settings > Accounts > Delete Account.

Confirm removal, then close and reopen the Outlook app.

Add your account again and allow time for full synchronization.

Manually Load Older Emails

Open the folder that appears empty.

Scroll to the bottom of the message list.

Tap Load more conversations to fetch older emails from the server.

Repeat if needed until all emails are visible.

Restart Your Device

After completing the steps above, restart your iPad/iPhone to ensure all changes take effect.

I hope these steps help restore access to your folder on mobile. If you need further assistance, feel free to reach out anytime!

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Ryan-N 3,015 Reputation points Microsoft External Staff Moderator

2025-07-22T16:01:55.6733333+00:00

Hi Jay Goldman,

I hope the information I shared earlier was at least somewhat helpful in addressing your issue. If the previous methods haven’t been effective, please feel free to let me know. I’d be happy to explore the issue more deeply with you so we can work together toward a better solution.

If you found the answer helpful, we kindly invite you to mark it as the accepted solution. Once marked, it will automatically be pinned to the top. Since many other users also search for information in this community, your valuable contribution will help them easily find the right channel and useful insights more quickly.

Thank you very much, and I wish you a great day.

Answer 4

Jay Goldman 20

Hi Ryan. I’ve completed all the steps you suggested, but the issue still persists. It may be helpful to know that while some folders provide the option to “Load New Conversations”, the problematic folders don’t provide that option.

Ryan-N 3,015 Reputation points Microsoft External Staff Moderator

2025-07-23T17:56:35.5033333+00:00
Hi @Jay Goldman,

Thank you for your response. Additionally, you noted that while some folders offer the “Load New Conversations” option, the problematic folder does not.

Below are additional troubleshooting steps you can try:

Inject a New Email into the Problematic Folder

• On Outlook Web or Mac, move a recent email into the folder (or send yourself a test email and file it there). • Check your iPhone/iPad to see if the new email appears.

• If it does, try pulling down to refresh and see if older emails also show up.

Use the Search Function in Outlook Mobile

• Tap the search icon and enter keywords or sender names.

• If emails are found, you can open them directly from the search results.

Check Using Apple’s Mail App

• Add your Outlook account to the Mail app on iOS.

• Set “Mail Days to Sync” to “No Limit.”

• Check if the folder displays its emails.

Toggle Filters and View Settings in Outlook Mobile

• Ensure the view is set to “All Mail.”

• Try switching to “Unread” and then back to “All Mail.”

• Disable “Organize by Thread” in the app settings.

Try a Different Network or Allow More Sync Time

• Switch between mobile data and Wi-Fi.

• Leave the device charging with Outlook open for a few minutes to allow full sync.

Mailbox Maintenance (if applicable)

• If your mailbox is nearly full, consider archiving or deleting old emails.

• Move all emails to a new folder to refresh the index.

Contact Microsoft Support via the App If none of the above steps resolve the issue, it’s likely a technical bug within the Outlook app. In this case, we recommend contacting Microsoft Support directly through the Outlook mobile app:

• In the Outlook app, go to your profile > Help & Feedback > Contact Support.

• Briefly describe the issue and the steps you’ve already tried so the technical team can assist further.

We hope these steps help you resolve or better understand the root cause of the issue. If you need further assistance during the process, please don’t hesitate to reach out to us.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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Jay Goldman 20 Reputation points

2025-07-23T18:31:47.8566667+00:00

Ryan, I think you're a genius. The suggestion to "Check Using Apple’s Mail App" and the related instructions seemed to fix the problem.

THANK YOU!
Ryan-N 3,015 Reputation points Microsoft External Staff Moderator

2025-07-23T20:30:29.1133333+00:00

Hi @Jay Goldman,

Thank you for your response. It’s great to know that the information I provided was helpful to you.

If you have any questions or concerns, please feel free to share them with me. I’m always happy to help.

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Outlook for Mac and Web is deleting emails I send to myself, and will not allow me to delete any emails myself

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