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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!
Using older versions of Outlook for Mac in business environments
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.
Every message I send with attachments or messages sent to me with attachments such as PDFs are returned as undeliverable spam.
Please advise. Eric
Glenn Aro
Can you provide me with Tzamarin's solution so I can get attachments sent. Thank you very much
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)'
How do I revert back to the old version of Outlook? Apparently my computer updated overnight because it was working fine yesterday. ; (
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!