You've drafted a contract. Two people need to sign it. You'd rather not pay $40/month for DocuSign just to handle this once. Here's what your options actually look like — and what each one costs you in time, friction, or legal exposure.
Print two copies. Both parties sign both copies (each keeps one). Scan the signed copy for a digital record.
When it's fine: Low-stakes agreements between people who are in the same room. A simple contractor agreement between you and someone you see regularly. Splitting the cost of something with a roommate.
Where it breaks: You can't be in the same room. The document needs a clear chain of custody. You're dealing with a company whose legal department requires a digital record. The scanned copy is a JPEG — nobody can verify it hasn't been altered.
Works for: in-person, low stakesCreate the contract as a PDF. Person A types their name in the signature field (or uses Preview / Adobe Reader's annotation tools to sign), saves it, and emails it to Person B. Person B does the same and sends back the final copy.
When it's fine: You trust the other party and just need something documented. You're okay with the fact that it's technically disputable. Internal agreements where legal enforcement is unlikely.
Where it breaks: The chain of custody is murky. Who signed which version? Did Person B sign after Person A modified the document? The email thread is the only evidence, and email threads are surprisingly easy to reconstruct falsely. If you ever need to prove this in court, you'll be explaining why you did it this way.
Works for: low-trust-risk agreements with someone you knowDocuSign offers a free plan — but it caps you at 3 envelopes per month. The free plan from HelloSign (now Dropbox Sign) is similar: limited, with restricted storage. Smallpdf and SignNow also have free tiers.
When it's fine: You genuinely only need this once or twice a year, and you're willing to use a different email address when the free limit resets. (We're not endorsing this workaround — just naming it.)
Where it breaks: You need multi-party signing (more than two parties is often a paid feature). You want to keep the document long-term in a place you can retrieve it. You need a real audit certificate, which free tiers often watermark or omit.
Works for: occasional use, simple two-party agreementsThe main complication with getting two people to sign is sequencing. Usually: Party A signs first, then the document is sent to Party B to sign. The final executed copy — with both signatures — then needs to be delivered to both parties.
In the PDF-over-email approach, you manage this by hand. Someone has to keep track of who signed what, which version is final, and who confirmed receipt. That works until it doesn't — usually in the one case where you wish it had.
In a proper signing tool (even a free or cheap one), the sequencing is handled for you: Party A gets an email, signs, the tool routes to Party B, Party B signs, both parties automatically get the executed copy and its certificate. Nobody has to manage the chain.
filefriend is a software tool, not a law firm. This article is general information, not legal advice. For high-stakes agreements, consult a lawyer.