Why does this one particular email that I edit & resend to myself daily keep disappearing?

Question

This happens in both the Outlook 2019 on my PC and in the Outlook for iOS on my iPhone, which both only have my 1 outlook.com email address in them.

I should say, since it might tell someone who knows more than me, that on my iPhone's Outlook, this email will appear momentarily in the Inbox after I 'Edit or View Recipient", Reply or Forward to myself and the Send it. It doesn't appear at all ever in the Inbox in the Outlook 2019 on my PC. I luckily learned to just go get it from the Sent folder and Move it into Inbox on both devices.

I've tried everything I can think of to stop it from happening. It's weird how the email will show up in the Inbox on my iPhone's Outlook momentarily, but then it disappears. It doesn't go into the Deleted folder. The only place I can find it is in Sent, so I just always highlight it and Move it to Inbox. Then it's happy living there. This has been going on for over a month.

Maybe I have a Rule setup that automatically Permanently Deletes it based on some word that it finds in the Subject or Body text? I know I've setup a few Rules somehow in the past so that I'll stop seeing repeated Spam, but I don't know how to find those to examine them, looking for any specific word. Does that even seem like what might be going on?

This is the only email that this happens to and oddly it happens regardless of where I do the Reply and Send from, my PC or my iPhone. Otherwise, my Outlook works perfectly on both. I love having Outlook on both since it keeps my life in sync 24/7 with Inbox, tons of email folders & Contacts, Appointments and Tasks (To-Dos on the iPhone's free To-Do app)

BTW, I never use Microsoft's "live" server version of Outlook. I use my programs and my iPhone's APPs instead.

Here's a PrintScreen image of it that I just Moved from Sent to Inbox to recover it. I removed me email address after my name using Paint Shop Pro for security reasons. [PII: Removed]

Answer 1

Please note that this is a user-to-user community. As moderators, I have limited access to internal development details. My role is to direct users to the appropriate support channels and resources. While I cannot provide backend analysis, I will do my best to assist you within my responsibilities.   

 Please note that our forum is a public platform, and we will modify your question to hide your personal information in the description. Kindly ensure that you hide any personal or organizational information the next time you post an error or other details to protect personal data. 

---

Thank you for the update Jeff Davis

Please try the steps below.

1) Check Outlook.com rules from the web mailbox

Even if you normally use Outlook 2019 and the Outlook app on your iPhone, please check Outlook.com in a browser once. Outlook.com rules can run directly on the mailbox before the message fully syncs to Outlook 2019 or Outlook for iOS.

• Go to Outlook.com Mail and sign in with the same Outlook.com account.
• Select Settings.
• Go to Mail > Rules.
• Review each rule carefully.

Look especially for rules with conditions such as:

• Subject or body includes specific words
• Sender is your own email address
• Message includes certain text

Also check for actions such as:

• Delete
• Move to another folder
• Mark as junk
• Forward or redirect

If you find a suspicious rule, turn it off temporarily using the rule toggle. Then send the same test email to yourself again. If the message now stays in the Inbox, edit or delete that rule.

2) Check rules in Outlook 2019

Please also check classic Outlook because Outlook 2019 can have rules that may not appear exactly the same way in Outlook.com.

• Open Outlook 2019.
• Select File > Manage Rules & Alerts.
• On the E-mail Rules tab, make sure your Outlook.com account is selected.
• Review the rule list.

Look for anything that mentions:

• Specific words in the subject or body
• Delete it
• Permanently delete it
• Move it to a folder
• Messages from yourself
• Messages sent only to you

Rather than deleting a rule immediately, I suggest unchecking the suspicious rule first. Then send the same message to yourself again. If the issue stops, go back to File > Manage Rules & Alerts, select the rule, and choose Change Rule or Delete.

3) Back up your Outlook 2019 rules first

If you have several rules and are not sure which one is causing the problem, back them up before making major changes.

• In Outlook 2019, go to File > Manage Rules & Alerts.
• Select Options.
• Select Export Rules.
• Save the backup file.
• After that, disable rules one at a time and test again.

This makes it safer to troubleshoot because you can restore your rules later if needed.

4) Check Junk Email and blocked sender settings

Since the message is being sent from yourself to yourself, also check whether your own email address or domain was accidentally added to a junk or blocked sender list.

In Outlook.com:

• Open Settings.
• Go to Mail > Junk email.
• Check Blocked senders and domains.
• If your own email address or domain is listed, remove it and save the change.
• You can also add your own address to Safe senders and domains, then test again.

5) If you find the rule, edit it instead of deleting it completely

If the rule was originally created to stop spam, you may not need to delete it. You can make it safer by editing the rule instead.

For example, you could:

• Remove the specific word or phrase that is matching your personal note
• Add an exception for messages from your own email address
• Change the action from Permanently delete it to Move it to Junk or another folder
• Rename the rule so it is easier to identify later

Please tell me how it goes. If the problem persists, please don’t hesitate to reply to this thread and I will be happy to help. Have a lovely day!  

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

Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread