Hello George,
Thank you for participating in the Apple Support Communities! We understand that when sending email attachments using Mail Drop on your Mac, they are failing to send.
Let's start by confirming that one of the emails that you're attempting to send meets the Mail Drop limits outlined here:
Mail Drop limits - Apple Support
You may also want to try compressing the file as suggested here:
If iCloud Mail isn't working - Apple Support
Message attachments can't exceed the maximum size allowed by your email service provider or the recipient's email service provider. The maximum size varies by service provider. Try using Mail Drop, compressing the file before sending it, or sending your message without the attachment."
One last thing to check would be to ensure that you have not exceeded your mailbox size and sending limits for iCloud:
Mailbox size and message sending limits in iCloud - Apple Support
Take care.