All sent messages with attachments arrive in recipients Spam

Hello, here’s a weird one. Recently started using EM Client after years of using Apple Mail on a mac, and Windows mail and Outlook 365 on Windows.

The only problem is every singe email I sent that has an attachment (any kind of file) arrive in my recipients Spam folder. They all get filtered without exception, it doesn’t matter if it’s a reply to a known contact, there is no eception, every ewmail sent with an attachment gets filtered.

Using the other email clients (Outlook, Windows Mail) it does not. Settings between clients are identical (server, ports etc)

What could cause this ?

Have a friend open the message and look at the headers. See if there is anything such as precedence : bulk or something silly on the eMC originated messages.

I suspect there is a header getting set (or not set) by eMC that causes the recipient’s client (or possibly server) to view it as a spam message.

I’m also assuming (dangerous) that your multiple friends are using different clients and not on the same mail host (i.e they are not all on gmail or outlook/hotmail).

Thank you for responding. None of us are using public email services.

I think I may have found the issue. When I added my account, I did set the imap settings (server, port, authentication) manually but for some reason EMClient have change them, i never noticed that. I set them back manually from 143 and 587 Force to 993 and 465 Legacy (which is what I’m using for other email clients I used) and did a few emails to a friend and they all arrived in the inbox.

Still a bit weird that with the settings auto-set by EMClient I would have full functionality except all emails with attachment being marked as spam.

Hopefully this will work with all my contacts, will report back here

Interesting. I wonder if the headers had something that indicated the lack of SSL/TLS or something, and the recipients were using that to indicate higher suspicion of spam.