You sent the proposal. Then you noticed page 4 had last quarter's pricing. Resend. Apology. Then the file was 40 MB and bounced. Resend smaller. Apology. The client now thinks you can't get it right.
Four habits prevent the resend cycle.
Habit 1: Last-page check
Before any external send, scroll to the last page of the PDF. Confirm it's actually the end. The number of PDFs sent missing their last page is shocking.
Also check the first page — cover correct, name spelled right, date current. Thirty seconds, big saver.
Habit 2: Compress to under 10 MB
Anything over 10 MB risks bouncing. Compress every external PDF as a reflex, not an afterthought. Five seconds, eliminates the bounce-resend cycle.
If it won't compress under 10 MB without quality loss, use a share link instead of an attachment.
Habit 3: Flatten if signed
Unflattened signatures can be moved by the recipient. They also flag 'amateur' to anyone who notices. Flatten before sending.
Flint flattens automatically on sign-and-download. Verify by opening the signed PDF and trying to drag the signature.
Habit 4: Final naming pass
Rename to `<context>_<doc-type>_<date>.pdf` before attaching. Drafts are named `v1`, `v2`; finals are not. A filename of `Proposal_FINAL_v3.pdf` makes the recipient ask 'is this really final?'
The filename is part of the message. Make it confident.
FAQ
What about errors I genuinely couldn't catch?
Some errors only surface after the recipient reads. Those are forgivable. The preventable ones — wrong file, wrong size, unflattened — are not.
Should I read every PDF before sending?
Yes, end-to-end, for anything externally facing. Five extra minutes saves the credibility damage of resends.
How do I recover from a resend?
Short, professional, no over-apologising: 'Apologies — the right version is attached.' Move on. Don't dwell.
Does this matter for internal sends?
Less, but still. Internal resends train colleagues to expect updates to be coming, which slows everyone down.
Resends are mostly preventable. Run the pre-send checklist in Flint on every external PDF and feel the apologies disappear.