Outlook showing emails 'sent' but not received by recipients

I have what seems to be exactly the same problem: When I send an email, it shows up under "Sent Items", but doesn't reach the recipient. I don't get any message of failed delivery or any other error message. I've even tried sending test emails to myself (the same email address), with the same result - appearance under "Sent Items", but not in the Inbox. It doesn't appear under "Junk" either.

As far as I can tell, I can still receive emails from others just fine.

For me the problem started sometime in the last 24 hours. As far as I know, I have not experienced this problem before. For reference, I'm using outlook.live.com in my browser.

https://outlook.live.com/

I can send an email from my live account to other non-microsoft accounts I have (which are working/receiving fine).

The email gets moved to the Sent folder but it never arrives at my other accounts Inboxes.

https://portal.office.com/servicestatus - is all OK

What is the deal?

I have the exact same problem. I have no idea where these emails disappear to. Outlook does not provide any error messages. My email is in the "sent" folder. The reciepient is a person to whom I send many emails. Most are received. Periodically, they are not. I have put in place the following temporary solution.
I have another email account in gmail. I always cc my emails to this account as well sending to my recipient.
After sending the email, I check my gmail account to see if it has been received.
If it has not been received in my gmail account, I check with the recipient to see if he has received my email. !00% of the time he has not received it.
I use my gmail account to send the email with exactly the same contents and subject line. I also cc my outlook account. The email is received by both the recipient and in my outlook account.

I do believe that there is a bug in outlook which periodic. It only happens occasionally. So now, I always cc myself on my other account to be sure that an email is received by the repicient(s).

Hi.

The email that did not reach a receptionist, used to remain in the Sent folder. Now I cannot find it in the Sent folder. Where is it now? I do not want to type again this long Mail.

Kind Regards

Eli Henig

******@gmail.com

Dear Samet Thank you for the quick response.

I apologize for misunderstanding the scope of your problem. You're absolutely right, if the issue is specifically with emails between your MSN and Hotmail accounts, then checking SPF, DKIM, and DMARC wouldn't be the most relevant initial approach.

Here are some more focused steps you can take to diagnose and resolve the intermittent email delivery issue you're experiencing:

1. Investigate Recipient's Settings:

Junk Folder Check: Ask the recipient using the Hotmail.com account to double-check their spam and junk folders, in case your emails are being unintentionally filtered. See if your MSN address is accidentally added to the recipient's blocked sender list, preventing delivery. Some email providers like Hotmail have specific filters based on content or sending patterns.

2. Analyze Email Headers: Use a tool like MXToolbox or Email Header Analyzer to examine the email headers of your undelivered emails. This can reveal technical details like spam scoring and routing information that might indicate why your emails aren't reaching the recipient. Disclaimer: This is a non-Microsoft website. The page appears to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it.
3. Check Microsoft Server Issues: Occasionally, Microsoft's servers can experience temporary glitches or outages that might affect email delivery between specific services like MSN.com and Hotmail.com. "Check Microsoft's service status page to see if there are any reported issues: https://portal.office.com/servicestatus "

Additional Tips: Send a test email from your MSN account to another Hotmail.com account you have access to, to see if it delivers. For urgent communication, consider setting up a temporary email alias service to ensure consistent delivery while investigating the issue with your MSN account. Avoid sending bulk emails: Avoid sending bulk emails or emails with suspicious content from your MSN account, as this can raise spam flags and affect future delivery.

Remember, troubleshooting email delivery issues can often be a process of elimination. By following these steps you should be able to identify the cause of the intermittent delivery problem and implement solutions to ensure your emails reach Hotmail accounts reliably.

I apologize again for the previous misunderstanding and hope this revised information proves more helpful!

-Adedayo