Emails being blocked by Gmail from office 365

Anonymous
2023-03-02T23:25:26+00:00

When the emails is sent to gmail its being blocked stating

Delivery has failed to these recipients or groups:

___@___.___ (***********@gmail.com)

Your message wasn't delivered because the recipient's email provider rejected it.

all my records are up to date..

gmail.com suspects your message is spam and rejected it.

natasha.daniel Office 365 gmail.com
Sender Action Required
<br> --- --- --- --- ---
Messages suspected as spam
How to Fix It
Try to modify your message, or change how you're sending the message, using the guidance in this article: Bulk E-mailing Best Practices for Senders Using Forefront Online Protection for Exchange. Then resend your message.
If you continue to experience the problem, contact the recipient by some other means (by phone, for example) and ask them to ask their email admin to add your email address, or your domain name, to their allowed senders list.

Was this helpful?Send feedback to Microsoft.

More Info for Email AdminsStatus code: 550 5.7.350

When Office 365 tried to send the message to the recipient (outside Office 365), the recipient's email server (or email filtering service) suspected the sender's message is spam.

If the sender can't fix the problem by modifying their message, contact the recipient's email admin and ask them to add your domain name, or the sender's email address, to their list of allowed senders.

Although the sender may be able to alter the message contents to fix this issue, it's likely that only the recipient's email admin can fix this problem. Unfortunately, Office 365 Support is unlikely to be able to help fix these kinds of externally reported errors.

Original Message Details

Created Date: 3/2/2023 11:29:38 PM
Sender Address: *********@*****.com
Recipient Address: *********@gmail.com
Subject: Email check

Error Details

Reported error: 550 5.7.350 Remote server returned message detected as spam -> 550 5.7.1 [2a01:111:f403:700f::715 19] Our system has detected that this;message is likely suspicious due to the very low reputation of the;sending domain. To best protect our users from spam, the message has;been blocked. Please visit; https://support.google.com/mail/answer/188131 for more information. c23-20020aa7c997000000b004ace5dc6b61si945041edt.369 - gsmtp
DSN generated by: PN3P287MB0113.INDP287.PROD.OUTLOOK.COM
Outlook | Windows | Classic Outlook for Windows | For home

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

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  1. Anonymous
    2023-09-16T15:47:10+00:00

    jwwebwork.com

    I don't see domain on any blacklists.

    I just set up Google Postmaster tools and don't have data.

    SPF is checking OK on MX Toolbox. I did change it about 18 hours ago to v=spf1 include:spf.protection.outlook.com -all

    Before I had v=spf1 +ip4:192.185.179.149 +include:spf.protection.outlook.com -all

    which must have been generated when I set up Office 365 2 years ago.

    I am getting email through to some single gmail addresses, but when I send to groups I've had for a long time, I get this message below after about 1 day for all the gmail addresses.

    Would connector even help though?

    Delivery has failed to these recipients or groups:

    *.*@gmail.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

    Diagnostic information for administrators:

    Generating server: CY5PR12MB6525.namprd12.prod.outlook.com
    Total retry attempts: 14

    *.*@gmail.com
    Remote server returned '550 5.4.300 Message expired -> 421 4.7.28 [2a01:111:f400:7eaa::720 15] Our system has detected an unusual;rate of unsolicited mail originating from your IP address. To;protect our users from spam, mail sent from your IP address has been;temporarily rate limited. Please visit; https://support.google.com/mail/?p=UnsolicitedRateLimitError to;review our Bulk Email Senders Guidelines. y6-20020a17090668c600b0098e19ebc8fcsi3768633ejr.679 - gsmtp'

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  2. Anonymous
    2023-09-16T16:54:26+00:00

    Thanks for the info.

    The issue you are running into isn't the mail connector issue. It is a rate limiting issue.

    You mentioned that you are sending to a group that contains gmail address'. The only way to get around this, is to rate limit how many gmail address' you are sending to at one time.

    For example, if your group has 10 gmail addresses, and you send a message to that group. Gmail is going to think that it is bulk email, which it does not allow. Because all those messages are being sent at one time.

    But if you send to just a single gmail address, it would go thru (obviously not right after you got rate limit blocked).

    As I said earlier, the only way around it is to throttle your messages to gmail. Unfortunately, exchange online does not have this feature (at least nothing I have found). An exchange server that you host yourself has that ability.

    Thus the only work arounds are to:

    1. remove the gmail address' out of that group and send one at a time.
    2. Use a service such as Mailchimp. (you will need to add their info into your SPF record)
    3. You set up a smtp relay on a server you control, and relay your messages thru it. You can configure your relay to throttle the messages back. If you go that route, which is very easy to do on a windows server. You need to have a static public IP, and that IP needs to be added into your SPF record.

    There are a lot of free email services out there that I know of that do rate limiting; gmail and AOL are the two of the most strict.

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  3. Anonymous
    2023-09-16T18:35:36+00:00

    Thanks so much for the thorough answer.

    I will add: this has happened to a group of only 3 this week - custom domain Office 365 account to 3 gmail accounts.

    It was only in the last 3 weeks that I started getting the Outlook error messages for so-called bulk email.

    So, even emails sent from a gmail account to over 10 gmail recipients could not be recieved? Though I didn't get the error messages when doing this.

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  4. Anonymous
    2023-09-16T23:02:19+00:00

    I'm in the same boat as Janet. I'm an individual user with a subscription to MS 365 run by GoDaddy. I don't know anything about DNS or DKIM, but I know that a couple of weeks ago my reply (via Outlook) to a local board of directors (12 members) rejected all of the board members with Gmail addresses. Later it rejected a message that I sent to two friends with whom I regularly communicate by email (both have Gmail addresses) This just started for me, and sounds like for Janet as well. Something has happened, and it's not me! Please help, this is driving me crazy. I also can't "reply all" to messages from a local volunteer group that I participate in. This is crazy . . .

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  5. Anonymous
    2023-09-17T22:24:51+00:00

    The issue is with the IPv6 address the Microsoft server is using failing SPF, see my post on page 4

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