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. Ron-6928 4,991 Reputation points
    2024-03-12T15:57:41+00:00

    I'm guessing Yahoo seems to be having spam issue with Microsoft's SMTP servers and they either throttle email coming in from Microsoft (by deferring them) or reject them entirely. If you get a bounce mail notification, read what it says.

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  2. Anonymous
    2024-03-12T14:38:26+00:00

    Thanks for the detailed reply! I already configured DKIM several weeks ago to resolve the issues with emailing Gmail accounts. Everything seemed to be working great, but I noticed over the past week or two, I have not been able to email anyone from the yahoo domain. I’ve already configured DKIM and SPF. Everything is correct… the syntax and all. Is there anything else that I could be missing? I’ve tried using the tools referenced in this thread for checking to see if it’s configured properly, and everything appears to be fine. I can email Gmail and other domains without any issue, it’s just yahoo. That is the last one standing. I appreciate any and all feedback!

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