Signing link expired: why it happens and the fix

A signing link expires for one of three reasons: the request reached its deadline, the sender resent the invitation and the old link was replaced, or the sender withdrew the document. The fix follows from the reason. While the request is still live, the sender resends to that one person and the new link works immediately. Once the request itself has expired, nothing reopens it, and the sender creates a fresh request from the same PDF.

The rest of this post explains where the deadline comes from, what the signer actually sees, what a resend changes, and how to stop it happening on the next document.

Why signing links expire

Every envelope is given a thirty day life at the moment it is created. That detail matters more than the number. The clock does not start when you press Send; it starts when the draft first exists, so the days spent uploading the file, adding recipients and placing fields come out of the signers’ time. An envelope created on the first and sent on the twentieth leaves ten days to sign, not thirty.

Each recipient’s link inherits its deadline from the envelope when their invitation goes out. On an envelope with Sign in order switched on, later signers are invited only after the person before them finishes, but they get the same end date. In the employment contract example the employer countersigns only after the new hire accepts, so every day the employee takes is a day the employer loses.

There is a reason for any expiry at all. A signing link is a credential. OWASP’s session management guidance says every session should have an absolute timeout regardless of activity, because it limits how long a hijacked session can be used, and NIST’s authentication guidelines set hard reauthentication limits for the same reason. A request that could still be signed a year later, from an inbox nobody monitors, is exactly the kind of long lived token those documents warn about.

What the signer sees

A signer who opens a dead link does not get the document. They get a short page with one of two messages, and the wording is the only clue to what happened:

• This signing request has expired. The envelope passed its deadline.
• This document was withdrawn by the sender. The sender voided it.

A link replaced by a resend simply stops working, and the new invitation is sitting in the signer’s inbox. The difference between expiry and withdrawal is covered in more detail in void vs expire on an e-signature request.

Two other timeouts get reported as “the link expired” and are nothing of the kind. The signing session a person holds after verifying lasts thirty minutes and lives only in the open page, so a refresh or a long lunch sends them back to the verification step. And five wrong access code or one-time code entries lock that recipient out for fifteen minutes. Both are solved without the sender: verify again, or wait the quarter hour. Knowing which one a signer hit saves a pointless resend. The lockout rules are laid out in how to verify a signer’s identity.

Resending a live request

If the request has not reached its deadline, open the status page and press Resend on the row of the person who is stuck. The button is per recipient, so chasing one late signer does not put a second email in front of the people who already signed. It is offered only while the request is still out for signature, and it is refused for anyone who has already signed or declined.

Resend exists for three situations. The signer never found the first email, usually because it was filtered. The signer forwarded or lost it and you want one clean link in one inbox. Or the signer locked themselves out with wrong codes and cannot wait.

On deliverability, it is worth remembering that the invitation is an automated email competing with everything else a mail provider filters. Google’s sender guidelines require every sender to authenticate with SPF or DKIM and keep reported spam below 0.3 percent, and warn that mail falling short might not be delivered as expected or might be marked as spam. You do not control those settings for a signing invitation, so the practical step is to phone or message the signer, confirm the address is right and ask them to check spam before you press Resend.

What changes when you resend

A resend is not a reminder. It changes the state of that recipient:

• The token rotates. The link in the earlier email stops working. Only the newest invitation opens the document.
• The viewed state resets. The recipient goes back to Waiting, so the status page no longer claims they looked at it.
• The lockout clears. Failed attempts go to zero and any lock is lifted. An access code you set stays the same.
• A fresh expiry, capped by the envelope. The new link is valid for whatever time the envelope has left, not for another thirty days.
• The trail records it. A resent event is appended, so the record shows why that recipient has two invitations.

That last point is why resending beats forwarding the original email. A forward leaves two live links for one person in two inboxes, and nothing in the record says so.

After the request has expired

Expiry is final. A sweep runs once a day at twenty minutes past midnight UTC. It marks every outstanding recipient Expired, marks the envelope Expired and appends an expired event to the audit trail. People who had signed stay signed in the record, but the document never completes, so no certified PDF and no certificate of completion are produced.

The way forward is a new envelope: upload the same PDF, add the recipients, place the fields again and send. The new request gets its own thirty days. Sometimes expiry is the right outcome rather than a nuisance. In the notice to vacate example, a notice nobody acknowledged within a month should be reissued with a fresh date rather than completed late, because the acknowledgement date is the whole point of the document.

The table below walks one request from creation to expiry, day by day, with what the signer’s link does at each stage.

Avoiding expired links

Most expired requests are avoidable with habits, not settings.

Create the envelope when the document is final. Because the clock starts at creation, a draft left open while a clause is negotiated eats the signing window. Finish the PDF first.

Choose parallel signing where order does not matter. In the residential lease example Sign in order is off, so both tenants and the landlord are invited together and signed the same afternoon. Sequential order is right when one signature must come before another, and it is the setting that makes the last signer’s window shortest.

Tell people the date. The invitation prints an Expires row, but a line in your covering message, such as “please sign by Friday the 12th”, does more.

Check the status page, not your memory. A Waiting badge a week after sending means the email may never have arrived. A Viewed badge with no signature means the person opened it and stalled, which calls for a conversation rather than a resend.

Common mistakes

• Resending to everyone. Resend is per person. Use it on the one row that needs it.
• Forwarding the original email. It creates a second live link and leaves no record.
• Resending when the signer’s session timed out. They only need to verify again from the same link.
• Letting a draft sit for two weeks. The signers lose those two weeks.
• Expecting to extend the deadline. There is no extension; plan the new request instead.
• Voiding and resending the same wrong file. If a request expired because the document was disputed, fix the document before sending the new one. A decline with a reason, as in the contractor agreement example, is the signal to change the terms, not to resend.

Build it

Every envelope expires thirty days after creation, the invitation email shows the expiry date, and a nightly sweep marks outstanding recipients and the envelope expired. Resend rotates one recipient’s link, clears their lockout and records a resent event; a voided link says the document was withdrawn. The signature request expiry page covers the timing, the resend page covers the rotation, and the steps for preparing and sending the envelope are in the tutorial send a document for e-signature.