Message blocked because it contains content identified as spam. AS(4810) - PDF issue

Anonymous
2023-11-06T05:01:14+00:00

I am trying to send a PDF attachment and I keep getting the message that it's been identified as spam. I haven't had this issue until tonight, and PDF attachments worked 24 hours ago. This is happening from multiple recipients: Gmail, Yahoo, .me, etc.

Things I've tried:

Test emails without the attachment (they go through)

Test emails with a different PDF attachment that I sent yesterday (they don't go through)

Test emails with different text in the subject and message body, and with the attachment (they don't go through)

Test emails with the file as a .fdx (Final Draft) rather than PDF (they go through)

Test emails as a One Drive link rather than an attachment (they go through)

Renaming the PDF file (it doesn't go through)

So it appears to be a PDF issue. I'm accessing Outlook on my browser using Chrome on a MacBook Pro. For work purposes I need to be able to send PDF documents as attachments, so I'm hoping to get this figured out soon. I work in a television writer's room so 7 million viewers are depending on me!

Thanks so much for any advice!

Outlook | MacOS | Legacy Outlook for Mac | For business

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  1. Anonymous
    2023-11-06T19:41:31+00:00

    POSSIBLE WORKAROUND: Use the full-blown Microsoft Outlook client.

    My mom started having the same issue today. I support her remotely via Quick Assist. BTW, I used to work for Microsoft.

    She is using the new Windows Mail client that is scheduled for release next year. I determined that seems it is specific to the mail client. Apparently, it affects people coming in on the Windows client and the browser client. It also affects any email sent with a PDF attachment but does not affect other emails with attachments like XLSX or DOCX or FDX.

    However, when I send the same exact same PDF attachment using the full-blown Microsoft Outlook client, it does NOT bounced by the spam filters and goes through with no problems.

    Not sure what changed but I've got to believe this has got to be affecting a lot of people.

    If someone from Microsoft is following this thread you may want to escalate this to the Outlook.com and hotmail.com support teams.

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  2. Anonymous
    2023-11-06T19:41:43+00:00

    Thank you for your kind words but I am undeserving of them.

    The workaround solution was provided by another user on this thread earlier today ('way back at the bottom of Page 2), tzamarin, is the one worthy of your praise. I was just passing along the fix when I tried it out and it worked. Cheers!

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  3. Anonymous
    2023-11-06T19:59:28+00:00

    How do I revert back to the old version of Outlook? Apparently my computer updated overnight because it was working fine yesterday. ; (

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  4. Anonymous
    2023-11-06T20:10:31+00:00

    So Is this just a forum where all of us share that we are having the same problem and Microsoft does not respond. We are all just supposed to brain storm and see if we can fix it ourselves. How do they not have customer service. This is mind blowing. This is my business email and I cant send info to my customers. So frustrating

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  5. Anonymous
    2023-11-06T20:16:22+00:00

    Not only does Outlook.com email have this problem sending any email with PDF attachments today 2023-Nov-6.

    It also suggested in the message blocked (bounce) response that the problem was on the receiving side - totally misleading.

    Embarrassed myself by telling the non-outlook recipient that they had a problem, based on that false finger-pointing diagnostic.

    My workaround is to switch over to Gmail for sending emails with PDF attachments, until normal outlook service resumes.

    That worked great.

    Did one little test to see if my outlook.com account could receive an email with a PDF attachment SENT to it from Gmail.

    That also worked for me.

    Below is the first part of the outlook.com sender bounce diagnostic msg - totally misleading - outlook send messed up!

    "

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

    Diagnostic information for administrators:

    Generating server: MN2PR14MB4223.namprd14.prod.outlook.com

    ____________@outlook.com
    Remote server returned '550 5.7.520 Message blocked because it contains content identified as spam. AS(4810)'

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