PDF Guides
How to eSign and Email a Contract Within Your Attachment Limit
A signed contract that bounces back with an 'attachment too large' error is a bad way to close a deal. Between signing it and sending it, there are two separate things to get right: adding a legally usable signature, and making sure the file is small enough for your email provider to actually deliver.
What your email provider actually allows
Gmail's own support documentation states a 25MB limit per message for personal accounts (Google Workspace admins can set a different limit for work or school accounts). Microsoft's Exchange Online — the mail service behind most Microsoft 365 business accounts — defaults to a 35MB send limit, adjustable by an admin between 1MB and 150MB. Outlook.com's consumer service states a 25MB limit on its own support pages.
In practice, a signed contract rarely gets anywhere close to these limits on its own — the more common problem is a contract bundled with several scanned exhibits, appendices, or ID copies, which is where file size adds up fast.
Signing the contract without printing it
Printing a contract just to sign it and scan it back in adds a step that isn't necessary anymore. A browser-based signature tool lets you draw, type, or upload a signature and place it directly on the PDF.
- Open the contract PDF in a signing tool
- Add your signature (and initials, if the contract needs them on multiple pages)
- Download the signed PDF
- Check the file size before attaching it to your email
Getting a bundled contract under the limit
If the file is too large after combining the signed contract with supporting exhibits, compressing it is usually the fastest fix and rarely affects the text's readability. If it's still too large after that — which is unusual for a document-only PDF — splitting it into a main contract plus a separate exhibits file, sent as two attachments, is a reasonable fallback.
A quick workflow that avoids the problem entirely
Sign first, then check the size, then compress only if needed — in that order. Compressing before signing risks having to redo the signature step if the compression settings change how the page renders, so it's simpler to treat compression as the last step before sending.
If the recipient is on a different email service
The limit that matters is usually the smaller of the two — yours and theirs. If you're on a Microsoft 365 business account with a 35MB allowance but you're sending to someone on a personal Gmail account, their 25MB inbound limit is effectively what governs whether the email goes through, regardless of what your own provider allows you to send.
Frequently asked questions
What's Gmail's actual attachment size limit?
25MB per message for personal Gmail accounts, according to Google's own support documentation. Google Workspace administrators can set a different limit for business or school accounts.
What about Outlook or Microsoft 365?
Outlook.com's stated limit is 25MB. Exchange Online, which powers most Microsoft 365 business accounts, defaults to a 35MB send limit and can be adjusted by an administrator between 1MB and 150MB.
Is a typed or drawn signature legally valid for a contract?
For most everyday business agreements, a typed or drawn electronic signature is standard, widely accepted practice. Specific contract types or jurisdictions can have their own requirements, so check what applies to your particular agreement if you're unsure.
Should I compress the contract before or after signing it?
Sign first, then compress only if the file turns out to be too large. That way you don't risk having to redo the signature if you change compression settings.