Why can't I send email from Outlook (microsoft account) to a Yahoo or AT&T email account?

Anonymous
2024-01-16T21:00:39+00:00

For years, I have been sending emails from Outlook on my desktop computer and mobile device with no problems. But the last few days, I am getting rejection messages saying my emails cannot make it through. Can I get help figuring out what is going on?

Here is the undeliverable error message I got when trying to send to an att.com email address (came from here: Mail Delivery Subsystem <******@xxxxx.prodigy.net>):

"The original message was received at Tue, 16 Jan 2024 12:28:35 -0800 from mail-mw2nam12on2049.outbound.protection.outlook.com [40.107.244.49] ----- The following addresses had permanent fatal errors ----- (reason: 554 [RL02] Message content not accepted for policy reasons; see https://postmaster.yahooinc.com/error-codes) ----- Transcript of session follows ----- ... while talking to mx-sbc.mail.am0.yahoodns.net.: >>> DATA <<< 554 [RL02] Message content not accepted for policy reasons; see https://postmaster.yahooinc.com/error-codes 554 5.0.0 Service unavailable"

And here is the undeliverable error message I got multiple times when trying to send to a yahoo.com email address (came from: Microsoft Outlook <******@xxxxxxx.com>):

"Delivery has failed to these recipients or groups:

(******@yahoo.com)
Your message couldn't be delivered. Despite repeated attempts to contact the recipient's email system it didn't respond.

Contact the recipient by some other means (by phone, for example) and ask them to tell their email admin that it appears that their email system isn't accepting connection requests from your email system. Give them the error details shown below. It's likely that the recipient's email admin is the only one who can fix this problem.

For more information and tips to fix this issue see this article: https://go.microsoft.com/fwlink/?LinkId=389361.

Thank you for help.

Outlook | Windows | New Outlook for Windows | For home

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  1. Anonymous
    2024-03-12T03:00:21+00:00

    There was a fix posted on Page 5 of this forum post that corrected this issue for me. None of our Microsoft email users could send to any Yahoo addresses from our business domain. Yahoo updated their security settings recently, and they are requiring two forms of DNS security verification for Microsoft email accounts to be able to send to Yahoo accounts. Yahoo only required one until very recently, and Microsoft 365 email accounts only provide one form of DNS record verification when sending emails by default. I added 2 DKIM records to our Office 365 email domain today, and it did take about 8 hours to work itself out, but all users can now send to Yahoo freely. Adding two proper DKIM CNAME records to your DNS record will fix the issue. This link gives you the instructions for adding the necessary DKIM records to your domain, just make sure you use the proper syntax: https://learn.microsoft.com/en-us/microsoft-365/security/office-365-security/email-authentication-dkim-configure?view=o365-worldwide

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  2. Anonymous
    2024-03-12T03:25:37+00:00

    It has to be Yahoo targeting Microsoft. Even though Yahoo states in their latest documentation that for normal users only need SPF *or* DKIM clearly that's not working with Microsoft custom domain accounts.

    I've been able to successfully send mail from in-house email servers using an SMTP service using only SPF to Yahoo so it's not clear why they're targeting Microsoft requiring DKIM.

    Microsoft finally responded this morning to the ticket I opened on Saturday. By then I had already found the answer. I explained to the agent that adding a DKIM record solved the problem, this was the agent's response:

    ..Your insight and experience will be valuable for other customers who may encounter similar issues. I will proceed with archiving this service request and share the information with the team as a possible resolution..."

    What's worse is that his first response to the issue (before I told him about DKIM) was to tell me to contact Yahoo.

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  3. Anonymous
    2024-03-12T13:51:18+00:00

    It appears to be resolved now. I added 2 DKIMs and SPF to my Turbify(yahoo) mail server. It took 12 hours to take effect.

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  4. Anonymous
    2024-03-12T13:54:30+00:00

    It appears to be resolved now. I added 2 DKIMs and SPF to my Turbify(yahoo) mail server. It took 12 hours to take effect.

    Are you able to reproduce the steps to fix the issue?

    Thanks.

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  5. Anonymous
    2024-03-12T14:11:55+00:00

    Yes. I'll post later today. I use 365. I signed in under admin. Went to the domain section under setup. Ensured that my Microsoft domain had dkims enabled. Clicked continue. Separate window, logged into turbify/yahoo admin. Copied dkims from Microsoft to turbify. Clicked Continue on Microsoft admin. Updated/Copied spf and other records from Microsoft to turbify. Clicked continue. It took 15 minutes from turbify to update records. Clicked continue on Microsoft until records were updated. Clicked save and/or closed both windows. Sent test emails from Microsoft to yahoo at 1900 EST. Emails came through/resolved at 0700 EST today. Sent test email to confirm. Emails went through with no issues

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