I have never had a problem sending PDF files, specifically the contracts I send out to clients. I've been doing it the same way for years. All of a sudden, I think it corresponded to this latest system update to MAC OS Sequoia. It's driving me crazy!!!
[Re-Titled by Moderator]
MacBook Air
I haven't seen anything specific with Sequoia that would point to the cause, but the 550 - Spam bounce back is common with specific email providers based on their filtering.
Tracking down these issues is difficult and with a single email provider, it is probably best to focus on that one to see if you can get further information about what is making them bounce back your PDF. If you have another device, such as a phone, it may also be helpful to see if you get the same bounce back.
Are you receiving a bounce back message from the recipients email provider, and if so is the message linked to a specific reason number such as 550 or 554?
I am sending my emails from Mail. Regular emails are making their way out to recipients, but anything I attach, like a PDF is being rejected. This has only been the last few days. I have not changed a single thing about the way I do things. I have not changed any setting either.
That’s usually on the recipient mail server junk mail filtering, or the recipient mail client local junk mail filtering, and not on your mail client sending mail.
It’s the recipient mail server and mail client that performs all spam filtering.
If you’re getting a 550 (there’s variously more detail with the 550), it’s the remote recipient mail server taking a dislike to your arriving mail messages.
Maybe also investigate an alternative to the use of mail attachments, or maybe using something else other than mail.
You can ask the recipient to add you to their contacts too, and to potentially ask their mail provider to allow this mail traffic through.
Update:
I cc-ed my gmail in the same email thread, so I tried to send the message using my gmail account and it went through just fine, but if I tried to send the exact same message, to the same recipients with my iCloud email then it gets rejected, so I think the issue lies on the iCloud server side.
Yes, they are giving a 550 message
Same here, MacOS Sequoia 15.5.
I have an email thread with a list of regular contacts and never had any issues until recently. Now I'm getting things errors like the following all the time. I already contacted the post master but have not received anything in reply.
<xxx@gmail.com>: host 127.0.0.1[127.0.0.1] said: 550 5.7.1
message content rejected due to spam; if you feel that your email was
rejected in error, please forward a copy to icloudadmin@apple.com (in reply
to end of DATA command)
I redesigned the .pdf contracts that I send out and made the file size smaller. It worked. They have been going through. Hope it works for you!
How to prevent emails from being marked as spam?
