I've been having a frustrating issue where I can't send emails with attachments from my Hotmail account. Whether it's a picture or a PDF, I get a message saying that the recipient's server won't accept it. Microsoft AI seems to think the files are too large, but that's not the problem since they aren't! This issue started a couple of weeks ago, and it occurs on all my devices including my iPad, desktop, and phone.
2 Answers
First off, how big are the files you're trying to attach? Sometimes, if they're over a certain limit, that can cause issues.
It sounds like something's going on with your account. Gmail has a send limit of around 25MB, but if nobody can receive anything from you, it might be time to consider switching providers. New accounts can be a breath of fresh air from constant spam, too! I found that adapting to new systems, like using labels instead of folders in Gmail, has surprisingly helped me stay organized.
I've actually opened a Gmail account because of this! I've been using my Hotmail for so long, switching is going to be a big adjustment.

Attachment file size doesn’t matter! Everything gets rejected. The message I get is: 'Your message wasn't delivered because the recipient's email provider rejected it.'