554 5.6.0 Invalid message content on Office 365 RRS feed

  • Question

  • We have a user that has a Office 365 account , also in thier Outlook, they are using a Gmail account. when they try and send from the Gmail account they get the following error. When I go into Outlook account properties for the gmail account and send a test email , it works. Any ideas how to trouble shoot this error?


    Technical details of permanent failure:
    Google tried to deliver your message, but it was rejected by the server for the recipient domain by [].

    The error that the other server returned was:
    554 5.6.0 Invalid message content

    Sunday, March 30, 2014 7:30 PM

All replies

  • Hi,

    According to your description, the error appears when the emails are sent from the Gmail account. If I misunderstand your meaning, please feel free to let me know.
    If yes, to understand more about the issue, I’d like to confirm the following information:
    1. Does the issue happens on all emails sent from the Gmail account or only emails with particular content?
    2. Does the issue happens on emails sent to Exchange server?
    If you have any question, please feel free to let me know.


    Angela Shi
    TechNet Community Support

    Monday, March 31, 2014 9:31 AM
  • I have a user with the exact same issue. He's also reporting that emails with attachments are taking several minutes to send. He's using Outlook 2007 for both his Office 365 Exchange account and his Gmail account. (He selects the "send from" address as needed to ensure he sends out from the correct account.)

    It is not happening with all emails that he sends.

    Please advise.

    Monday, May 5, 2014 12:55 PM
  • Anyone have found a solutions for this issue ? I'm facing the same problem with no luck so far...

    Wednesday, May 28, 2014 2:51 PM
  •  I'm facing the same problem. i narrow to mails in html format. e-mails in plain text and rich text go through like they should.
    Tuesday, October 14, 2014 1:20 PM
  • Also seeing this issue in past week only where the attachment is over a certain size, two incdients in past week where attachments zipped were over 8mb in size. Let me know if anyone has been able to get an answer to this one as it looks to be a new problem on EOP.
    Tuesday, October 28, 2014 2:47 PM
  • Hi Angela,

    I'm facing exactly the same issue. But it's limited to one domain only. I have two accounts configured in my Outlook 2010. One is Exchange and the other is Gmail. If I send a new email to my colleagues in same Exchange domain using the Gmail account in Outlook, I get the bounce back message "invalid message content".

    If I include two email IDs in same message, for example, and CC to, Yahoo gets delivered and Exchange fails. But Exchange is also limited to same domain.

    I noticed following in headers:

    From: Anil <anil***>
    X-Google-Original-From: "Anil" <>

    Do you think Exchange gets confused :) that why emails between users on same domain coming through Gmail.

    To resolve "Invalid Message Content" message, I also added my email ID in bypassed list of Exchange inbuilt Anti-spam content filtering but no luck.

    Wednesday, October 28, 2015 7:11 PM