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
    2023-11-06T22:09:33+00:00

    I searched online but kept running into issues trying to revert back to prior to today's version of Outlook ( apparently the 'update' is the issue (?) ).

    Most of the online articles address the 'toggle' feature for trying out the new outlook UI. This is NOT what happened ( I suspect to most of us ). Rather it was some auto update ( probably when I rebooted this morning ).

    Anyway, if anyone can post the easy, DIY, non - technical option to revert back to the Outlook version prior to today's drama, it would be great.

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  2. Anonymous
    2023-11-06T22:16:59+00:00

    Many thanks for the fine summary of workarounds until Microsoft fixes what they broke with their recent (unsolicited, as always) update.

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  3. Anonymous
    2023-11-06T22:25:32+00:00

    Thank you, but please help - Before I uninstall Windows Mail ( I am using the web version ), how do I now which version will be REINSTALLED ?

    Won't it just try to send/download the most recent version ( that is all hacked up today ) ?

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  4. Anonymous
    2023-11-06T22:34:37+00:00

    When you install the windows mail client, it installs the older one because the new one is still in testing phase until next year.

    To get the new one, you have to actively and intentionally select “Try new client”

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  5. Anonymous
    2023-11-06T23:00:13+00:00

    I am also using the web version and I can't thank the guys that came out with the workaround(s).

    1. change the email to text using the (...)
    2. combine the pdf files to .zip with a password
    3. save to draft and send with phone outlook - really lame but works
    4. use Gmail - I really like this one as it should piss off the Microsoft folks

    I also use my account for business and was appalled when I updated my computer that came with Win 11Pro (I'm really mad). Why do they screw with things that WORK!!!!

    Thanks again, guys

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