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
    2024-03-11T21:57:24+00:00

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  2. Anonymous
    2024-03-11T21:48:54+00:00

    I've been testing all day.. and all of the domains with DKIM send to Yahoo within seconds. I can't imagine it's an IP issue since mail is going through.

    Curious.

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  3. Anonymous
    2024-03-11T21:45:41+00:00

    Setting up a Microsoft account won't complete the Domain configuration until it sees all of the DNS records they require configured on the custom domain. I'll have to stick by my 99.99% number.

    Virtually every client with a custom domain I have on Microsoft O365 is experienced the problem. The SPF is a requirement only when you're enlisting a third party to send email on your domain's behalf. My clients aren't bulk emailing. According to Yahoo, the SPF should be sufficient for non-bulk senders.

    What it looks like to me is that Yahoo's SPF lookup is failing. I can set just DKIM and email goes through. But that still doesn't explain why Yahoo doesn't actively return an error to Microsoft instead of just disconnecting.

    I agree. Adding DKIM and DMARC along with SPF is no longer optional.

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  4. Ron-6928 4,991 Reputation points
    2024-03-11T21:33:21+00:00

    Update

    I just sent a test mail from my custom domain to my yahoo.com address. It is graylisted. I didn't have any problem, ever. A test mail arrived safely last week within a few second after sending it.

    There is clearly something going on between Microsoft and Yahoo mail servers. No one knows what it is.

    This is what I see in the message tracking log:

    Reason: [{LED=450 4.4.318 Connection was closed abruptly (SuspiciousRemoteServerError)};{MSG=};{FQDN=mta7.am0.yahoodns.net};{IP=67.195.228.109};{LRT=3/11/2024 9:18:56 PM}]. OutboundProxyTargetIP: 67.195.228.109. OutboundProxyTargetHostName: mta7.am0.yahoodns.net

    That IP address belongs to Microsoft and not blacklisted as of the time I sent the email.

    My test email finally arrived 11 minutes later. It should've been instant delivery (within a few seconds).

    At this point there may be multiple issues between Microsoft SMTP servers and/or IP addresses and Yahoo's.

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  5. Ron-6928 4,991 Reputation points
    2024-03-11T21:01:19+00:00

    >> I'd bet that 99.99% of the Microsoft custom domain users have proper SPF records.

    Many don't have an SPF record or multiple SPF records (this is a more common problem especially with GoDaddy customers). That's what I notice.

    The SPF and DKIM requirements are for bulk senders. We don't know who those people (who are having bouncing email problem) are. I would create all 3 records (SPF, DMARC and DKIM) to save the headache. I have all 3 and Yahoo does not reject my email (@custom domain)

    https://senders.yahooinc.com/best-practices/?guccounter=1

    Image

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