Attach a file to message

I need to send the contract revision to Elena in legal and to Marco in sales for signatures. Attach Contract_v3.pdf to a new email addressed to Elena Morales and Marco Rinaldi, subject Contract Revision — signatures needed, body: Hi Elena and Marco, please review and sign the attached contract revision. Elena should sign first, then Marco. I need both signed by Friday 10/22 because we must meet the customer’s renewal deadline. Confirm the file attached before you send.

Before I send this to Elena in legal, make approving this contract obvious. Put the key change summary and the net savings line at the top, bold the signature order (Elena first, Marco second), and move Contract_v3.pdf into a clearly labeled attachment named Contract_v3_FOR_SIGNATURE.pdf. Flag anything that might make Elena pause, like the new indemnity clause and the deadline of 10/22.

I created a new message to Elena Morales and Marco Rinaldi, dragged Contract_v3.pdf into the compose window, but the attachment didn’t appear and the Send button is active. I’m worried Elena will get an unsigned version and blame me. I don’t know if the file is blocked by size or the server. Should I try attaching again, upload it to our shared drive and link it, or convert it to a smaller PDF and retry? Which is fastest and safest for a Friday 10/22 deadline?

I keep sending emails about contracts without double-checking that the attachment is actually included; clients reply asking where the document is and we lose credibility. Over the last quarter this has happened three times, costing follow-up calls and missed deadlines. What simple habit can I build into my send routine so every outgoing email with an attachment is checked and verified, without adding more than 30 seconds per message?