Guide
How to Chase a Pending Signature
By Keelstar Team · Updated June 1, 2026
The short answer
Track every outstanding request with sent date, signers completed, and deadline. Send structured reminders before escalation, route blockers to the right owner, and cancel or replace stale requests instead of sending duplicate links. Chasing over ad hoc email loses context — automated reminders with a visible status do not.
Know what is actually pending
A request can stall because the external signer has not opened it, because an internal approver is waiting, or because signing order blocked the next party. Before chasing, check status: sent, viewed, signed, or declined. Generic 'please sign' messages annoy people who already signed.
Set a clear deadline upfront
Deadlines create urgency and give you a legitimate reason to follow up. Include the deadline in the original request and in reminders. For contracts tied to a start date or funding milestone, reference that date — it helps signers prioritize.
Reminder cadence that works
Start polite and increase specificity. First reminder: short, with a direct link. Second: note the deadline and offer to answer questions. Third: escalate to your internal owner or the counterparty's project sponsor. Avoid daily nagging on low-priority documents — it trains people to ignore you.
Escalation without burning the relationship
For vendor and customer documents, loop in the business relationship owner — the AE, CSM, or project manager — before going to executives. For internal documents, escalate to the signer's manager with context: what document, why it matters, and what is blocked. Keep all chase activity in the system or a single thread so history is visible.
When to void and resend
Void and recreate the request when the underlying document changed, the wrong person was listed, or the original link expired. Document the reason. Do not let two active requests for the same document float — signers may execute the wrong version.
Frequently asked questions
- How often should I remind a signer?
- A common pattern: reminder at 3 days, again at 1 day before deadline, then escalate to the request owner or the signer's manager for business-critical items.
- Should I send a new link if they say they cannot find the email?
- Resend from the same request when possible so the audit trail stays on one envelope. If you must recreate the request, void the old one and document why.
Related guides
Put this into a monitored workflow
Simple Signer handles this continuously — with reminders and an audit trail.