Dropbox Sign, formerly HelloSign, allows 3 signature requests a month on its free plan, with up to 3 signers per document and no templates of your own. Essentials lifts the cap for $15 a month billed yearly, with 5 templates. Countersigned Free sends 20 envelopes a month to up to 10 recipients each, and keeps up to 20 templates.
20 envelopes a month and up to 20 templates. Free forever.
DROPBOX SIGN · ESSENTIALS
Price / month$15
EnvelopesUnlimited requests, 5 templates
BillingBilled yearly ($180)
PER YEAR$180
COUNTERSIGNED FREE
Envelopes / month20
Reusable templates20
Reminders & signing orderIncluded
FREE FOREVER$0.00
$0to start sending on Countersigned. No trial clock.
$180a year for Dropbox Sign Essentials.
20envelopes a month on Free, with up to 20 reusable templates.
02/SIDE BY SIDE
What you get on day one.
Countersigned Free against Dropbox Sign’s own published plans. Dropbox Sign Free covers 3 signature requests a month and can’t create or save templates.
Countersigned Free compared with Dropbox Sign
Feature
Countersigned Free
Dropbox Sign
01Signature requests on the free plan
20 a month
3 a month Advantage: Countersigned.
02Signers per document on the free plan
Up to 10
Up to 3 Advantage: Countersigned.
03Templates on the free plan
Up to 20
Can’t create or save templates Advantage: Countersigned.
04Signer attachments
Included
Standard ($25/user/mo, 2 users minimum) Advantage: Countersigned.
05Signer access codes
Included
Standard and Premium Advantage: Countersigned.
06Dropdown fields
Included
Premium (custom quote) Advantage: Countersigned.
07Unlimited sending
200 a month on Pro ($20/seat)
Essentials, $15/mo billed yearly Advantage: Them.
08Integrations
None yet
Google Drive, Microsoft Word, HubSpot Advantage: Them.
PremiumUnlimited templatesCustom quote5 or more users
03/DO THE MATH
Slide to your real volume.
Pick how many agreements you send a month. We’ll find Dropbox Sign’s cheapest published plan that covers it, and ours.
1250
Dropbox Sign · Essentials$15/mo
Countersigned FreeFree
YOU KEEP EVERY YEAR$180
One sender, cheapest self-serve Dropbox Sign plan that covers your volume, at its listed monthly rate. Checked October 10, 2026.
04/IN FAIRNESS
Where Dropbox Sign still wins.
We’d rather you choose with the whole picture. If your files live in Dropbox and you send in volume, Dropbox Sign’s paid plans are a natural fit. If you’re on its free plan, Countersigned gives you more requests, more signers and real templates at the same price: $0.
01
Integrations with Google Drive, Microsoft Word and HubSpot, with Salesforce as a paid add-on.
02
SOC 2 Type II and ISO 27001, plus eIDAS and GDPR compliance claims.
03
Unlimited signature requests from $15 a month, billed yearly.
04
Bulk send, SMS authentication, branding and in-person signing on Standard.
05
Shareable template links and a separate API product.
05/HOW IT’S FREE
Built fast. Built carefully.
Free isn’t a trial or a teaser. It comes from how we build, and who builds it.
01 / BUILT WITH AI
A small team that ships like a big one.
The team behind DocuPipe spent a decade building machine-learning systems. Now we write, review and test Countersigned with AI at every step. That lets a small team run a complete signing product without legacy code or a large sales floor to fund, so the essentials can stay free.
It also means we move quickly. When something you need is missing, tell us.
02 / BUILT BY THE DOCUPIPE TEAM
Speed never skips the safeguards.
Countersigned is built by the team behind DocuPipe, the document-intelligence platform with ISO 27001:2022 certification, a SOC 2 Type II report and annual penetration tests. Those attestations cover DocuPipe, not Countersigned yet, but the habits came with us.
There’s no import tool yet, and you don’t need one. Your agreements are PDFs.
01
Create a free account
Email or Google. No credit card, no trial clock.
02
Rebuild your templates
Upload the PDFs you already send, place signer fields, and save up to 20 as reusable templates.
03
Send the next one free
Recipients sign in the browser without an account, and everyone gets the completed PDF.
07/QUESTIONS
Before you switch.
Is Dropbox Sign the same as HelloSign?+
Yes. HelloSign is now Dropbox Sign, owned by Dropbox. Its free plan, paid plans and API carry the Dropbox Sign name.
What does Dropbox Sign’s free plan include?+
3 signature requests a month, renewing every 30 days from sign-up, with up to 3 signers per document. You can send from Dropbox’s template gallery but can’t create or save your own templates. Countersigned Free includes 20 envelopes a month, up to 10 recipients each, and up to 20 templates.
How can Countersigned be free?+
We build with AI at every step, so a small team can run the whole product without a large sales organization to pay for. Free covers 20 envelopes a month and up to 20 templates, permanently. Teams that need more pay for Pro: $20 per seat per month for 200 shared envelopes. That, not your data, is the business model.
Are Countersigned signatures legally binding?+
Countersigned records each signer’s consent, signing events, IP address and browser, and produces a completed PDF with a completion record and document hashes. In the US, the ESIGN Act and UETA generally prevent a signature from being denied legal effect just because it’s electronic, but whether e-signing suits a particular agreement depends on the document and the law that applies. Countersigned doesn’t yet offer certificate-backed PDF sealing or qualified eIDAS signatures.
What if I send more than 20 envelopes in a month?+
Sending pauses until your allowance resets on the first of the month, or you can upgrade to Pro for 200 shared envelopes at $20 per seat per month. Signing and template reuse never use up envelopes; only sending does.
Do my recipients need a Countersigned or Dropbox Sign account?+
No. Recipients open a private link, review the document and sign in the browser. They don’t need an account or a subscription, and everyone gets the completed PDF.