Dropbox Sign (formerly HelloSign) vs. Docusign: Which should you use? [2025]

When was the last time you signed something with a pen and paper? Digital signatures are the way things are moving, which is why it's so important to have an eSignature app that you can rely on. Two of the most recognized solutions are Dropbox Sign (formerly called HelloSign) and Docusign.

I use Dropbox Sign to run my business, and I've used Docusign many times when signing contracts with clients. While they both offer a fast and convenient way to sign documents online, there are still some noteworthy differences.

I've been updating this article for a few years now, and this year, I spent even more time in each app to see how their features and workflows compare. Here's what I discovered in the Dropbox Sign vs. Docusign showdown.

Table of contents:

• Dropbox Sign vs. Docusign at a glance

• Dropbox Sign vs. Docusign: What's the same?

• Docusign is a dedicated eSign platform; Dropbox Sign is part of Dropbox

• Both apps are user-friendly, but Dropbox Sign is a bit more simplified

• Dropbox Sign is more affordable (especially for basic signing needs)

• Docusign is better for teams

• Both apps integrate with Zapier (but Docusign has more native integrations)

• Dropbox Sign vs. Docusign: Which should you choose?

Dropbox Sign vs. Docusign at a glance 

Here's the gist: 

• If you're looking for a basic electronic signing tool (without many extra capabilities), Dropbox Sign will be right up your alley. The tool gives you all the features you need to close deals quickly, save time, and sign legally binding documents. 

• Docusign, on the other hand, packs some really impressive functionalities—including AI-powered agreement management—to automate the agreement process and improve business operations for medium and large-sized organizations. 

Dropbox Sign vs. Docusign: What's the same?

Before we get into the differences, let's look at what's common between the two digital signature apps. Both apps:

• Are legally binding and include a real-time audit trail

• Offer in-person signing options on paid plans

• Have a working mobile app

• Include multiple languages

• Offer bulk send on team plans

• Include repeatable templates for documents

• Connect to third-party apps and integrate with Zapier

Docusign is a dedicated eSign platform; Dropbox Sign is part of Dropbox

Let's start with the basics. Docusign is a standalone, enterprise-grade eSignature platform built to handle the entire document lifecycle—from preparing and sending agreements to tracking, signing, and securely storing them. It offers advanced features like AI-powered contract analysis, workflow automation, and compliance tools, making it a strong fit for legal, sales, HR, and enterprise teams with complex needs.

Dropbox Sign, on the other hand, is a simpler eSignature feature built into the Dropbox ecosystem. It's designed to complement Dropbox's core file storage and collaboration tools, offering a convenient way to request signatures without leaving your cloud workspace. If you're already using Dropbox, it adds signing functionality right into your existing document workflow—no need to switch between apps.

Both apps are user-friendly, but Dropbox Sign is a bit more simplified

Once you log in to Dropbox Sign and Docusign, you'll notice they both offer a smooth user experience and nearly identical eSigning workflow: upload documents, add signers, place fields, and send. But even though the workflow is the same, I find Dropbox Sign a bit easier to use.

When preparing documents for signature requests on Dropbox Sign, you just need to add the signer's name and email, then complete your fields and send. The interface is straightforward with very few form fields.

With Docusign, you'll get a busier interface and workflow, prompting you to add signers, choose an envelope type and delivery option, add messages, and even choose the frequency of reminders. 

As you prepare your document inside the Dropbox Sign editor, you can easily replace it if you discover you've uploaded the wrong one. All you have to do is click the horizontal ellipses (…) next to the document you'd like to replace, select replace, and choose the replacement document. And after the replacement, the field placements will stay the same if the new document is the same size or has the same number of pages as the previous one.

Docusign's editor also has this replacement option, but it takes a bit of tinkering to find.

Dropbox Sign is more affordable (especially for basic signing needs)

Dropbox Sign and Docusign have similar pricing plans, but Dropbox Sign is much more affordable for individuals and small teams.

Free plans and trials

They both offer free monthly plans that include unlimited self-signing and three signature requests. On this free plan, you can add signature fields and basic information, send to multiple recipients in one bundle, and use the audit trail to track documents in real-time. They're both very generous, suitable for users that need to sign a few documents every few months. 

That said, Dropbox Sign allows you to test any of its paid plans for 30 days. Docusign doesn't offer free trials on paid plans, but it has a special 30-day trial account, which you can use to learn about the tool before committing (the trial account still lacks some paid features, and you'll have to sign up using a special link to access it).

Paid plans

After the free introductions, Dropbox Sign is cheaper for the basic features most businesses need for eSigning. 

The main distinction between the two entry-level plans ($20/month for Dropbox Sign and $15/month for Docusign) is that Dropbox Sign includes unlimited digital signature requests every month, where Docusign limits you to five. That's a pretty stark difference.

To unlock Docusign's unlimited signature requests, you have to buy one of the team plans, Standard or Business Pro, which start at $45 and $65/user/month, respectively. Dropbox Sign has a cheaper team plan starting at $30/user/month.

If you're a Dropbox user, you can get unlimited self-signing and three signature requests per month on any of Dropbox's paid plans. This means you don't need to buy a separate Dropbox Sign subscription if you're only signing a few documents every month.

The difference in pricing is clear. If budget is a big factor for your business, then you already have your answer. Dropbox Sign offers all the basic features you'll need at a lower price.

Docusign is better for teams

It makes sense why Dropbox Sign is cheaper: its feature set is very limited compared to Docusign.

Docusign gives teams access to robust features like delegated signing, custody transfer, insightful reporting, and options for providing signers with a more professional signing experience, like conditional fields, dropdowns, approval buttons, and read-only permissions.

When sending documents, you can use collaborative commenting to ask and answer questions within agreements. Set signing order, specify who views a document or receives a copy, and use pre-filled doc fields and automated routing to save time. You can even automate post-agreement actions like archiving documents and exporting data to a CRM. 

Docusign also gives you more options to ensure the security of your documents, especially when managing multiple users. For instance, administrators can lock templates to limit changes to messaging, branding, and even recipients. You can even ask signers to verify their identity in multiple ways, like email access codes, ID verification, and knowledge-based authentication. You'll find these advanced features impressive—and even necessary—if you're an enterprise-level organization.

On top of all these, Docusign allows you to instantly collect payments after a document is signed. The tool connects to payment gateways like Braintree, Stripe, Authorize.net, and more. 

To be fair, Dropbox Sign's team plans aren't totally lagging here. They offer important features like signer authentication with access codes, signer attachments, and in-person signing. But the few advanced features that are similar to Docusign's—like document dropdowns and signer reassignments—are locked behind their premium plan, and you have to speak to sales for a custom quote in order to access them. 

Both apps integrate with Zapier (but Docusign has more native integrations)

Both apps provide basic integrations to platforms like Google, Dropbox, and Microsoft on all plans. But when it comes to more robust integrations, they offer very different capabilities: Docusign has over 900 native integrations, while Dropbox Sign has just over 20.

With Dropbox Sign, you can connect to enterprise-grade platforms like HubSpot, Salesforce, Microsoft SharePoint, and Oracle, to streamline the agreement workflow across your organization. These integrations are available on the Standard plan for $30/user/month.

Docusign, on the other hand, locks the majority of its robust integrations behind its enhanced plan. This means you can't connect to CRM providers unless you speak to sales for a custom quote. But it does connect to more work and productivity tools than Dropbox Sign (think: Zoom and Stripe).

Having said that, both Dropbox Sign and Docusign integrate with Zapier, so you can connect them to thousands of other apps and orchestrate all your business workflows. Automatically send signature requests from anywhere, upload newly signed envelopes to cloud storage, and integrate AI to make your work smarter. Learn more about how to automate Docusign and how to automate Dropbox, or try one of these pre-made workflows.

Dropbox Sign vs. Docusign: Which should you choose?

Both Dropbox Sign and Docusign are excellent eSignature platforms with similar workflows and outputs, but in the end, they're ideal for different use cases. Dropbox Sign is easier to use and more affordable, especially for single users and small businesses already using Dropbox. But Docusign offers advanced features that make agreement processes easier and better for bigger teams.

Related reading:

• How to manage your electronic signatures, automatically

• The best apps for freelancers

• How adding document automation to your workflows helps your business

• The best Docusign alternatives

This article was originally published in September 2022 by Brittney Thompson. The most recent update was in July 2025.