Email rejecting most emails I am sending via my files, google files, and others.

Question

My hotmail and outlook emails are not allowing emails that i have previous had no problems with sending to myself, dance sheets, stuff in google drive, in my files on ipad. It happens whether using Ipad or laptop.

Answer 1

I see the message is being rejected as spam when you send to yourself. Are you sending from your Outlook account to the same Outlook address or to another account?

Answer 2

Hi,

Are you getting any error message or does the email fail silently?

This usually happens due to attachment limits or blocked file types. Outlook only allows up to 20 MB per message, and some file types are blocked for security. Files from Google Drive or iPad storage may also fail if they are not fully downloaded before attaching. Save the file locally first, keep the size under 20 MB, or upload it to OneDrive and send it as a link instead.