--- title: Dropbox Sign (formerly HelloSign) Reviews meta_title: 'Dropbox Sign (formerly HelloSign) Reviews 2026: Details, Pricing, & Features | G2' meta_description: Filter 2283 reviews by the users' company size, role or industry to find out how Dropbox Sign (formerly HelloSign) works for a business like yours. aggregate_rating: rating_value: 4.7 review_count: 2283 scale: '5' date_modified: '2026-09-29' parent_category: name: Sales Tools url: https://www.g2.com/categories/sales-tools ---

Dropbox Sign (formerly HelloSign) Pros and Cons: Top 5 Advantages and Disadvantages

Quick AI Summary Based on G2 Reviews

Generated from real user reviews

Users appreciate the ease of use of Dropbox Sign, enabling quick document management without technical hassles. (9 mentions)
Users appreciate the time-saving benefits of Dropbox Sign, simplifying document management without the hassle of printing or scanning. (5 mentions)
Users appreciate the tracking features of Dropbox Sign, which provide clarity on document status and signer engagement. (4 mentions)
Users appreciate the easy integration of Dropbox Sign, facilitating seamless deployment and enhancing productivity in their workflows. (2 mentions)
Users love the easy sharing capabilities of Dropbox Sign, enabling secure and efficient collaboration on confidential documents. (2 mentions)
Users find document management challenging due to unclear retrieval steps and limited customization options for advanced needs. (4 mentions)
Users experience email delivery issues with delays and spam misplacement, complicating the signing process significantly. (2 mentions)
Users find Dropbox Sign has limited customization, making it challenging to manage multiple documents efficiently. (2 mentions)
Users find it challenging to track signature status, complicating follow-ups and progress monitoring within Dropbox Sign. (2 mentions)
Users find it difficult to track signatures, lacking clear visibility and easy data export options for progress monitoring. (1 mentions)

5 Pros or Advantages of Dropbox Sign (formerly HelloSign)

5 Cons or Disadvantages of Dropbox Sign (formerly HelloSign)

Pankaj B.
PB
Pankaj B.
Founder and CEO
Computer Software
Small-Business (50 or fewer emp.)
"Effortless Signatures with Seamless Dropbox Integration"
4.5/5
What do you like best about Dropbox Sign (formerly HelloSign)?

I love the ease of use of Dropbox Sign (formerly HelloSign), and the fact that it's free with my Dropbox account is a big plus. It's really convenient on my Mac because I can just right-click a PDF file, select 'Sign', and easily add my saved signature image on top of the document. It's also nice that it works inside Dropbox desktop folders, making the signing process seamless.

Its performance is really fast.

Onboarding is very good and allows dropbox/google login.

AI integration would be huge plus Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

I find the web version of Dropbox Sign better because it allows me to put multiple signatures on different pages. On the desktop version inside Dropbox folders, I can only sign the last page of a document. Review collected by and hosted on G2.com.

Dave M.
DM
Dave M.
T
Small-Business (50 or fewer emp.)
"Seamless Remote Collaboration with Secure Access"
4/5
What do you like best about Dropbox Sign (formerly HelloSign)?

I like the easy accessibility and updated documentation provided by Dropbox Sign (formerly HelloSign). Our team can access documents from remote locations, add to them in real-time, and do so securely. It is a great advantage to access documents and make any necessary changes in a secure manner. The initial setup was very easy, which I appreciated. Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

Sometimes I find it hard to tell when the last person has made changes, and it's ready for review. Sometimes that's a little difficult to decipher. Review collected by and hosted on G2.com.

Verified User in Consulting
CC
Verified User in Consulting
Small-Business (50 or fewer emp.)
"Security and Verifiability Concerns Undermine Dropbox Sign’s Credibility"
1/5
What do you like best about Dropbox Sign (formerly HelloSign)?

The main positive to using Dropbox Sign was that my clients appreciated not needing to create an account to sign documents. Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

As someone that exclusively works with government agencies and not-for-profit organizations, I'm required to use products with a certain level of security, trust, and verifiability in the work that I do. Numerous times whilst using Dropbox Sign, the authenticity and security of contracts and other documents have been questioned. For a number of reasons, I've had documented that had already been signed require edits. The fact that Dropbox Sign documents still retain their signing certificate after editing eliminates their credibility. If it weren't for the Dropbox name associated with it and general, basic familiarity, I would have been required to have hundreds of documents resigned. Neither of these are good situations for my business. Review collected by and hosted on G2.com.

Mark W.
MW
Mark W.
Founder
Staffing and Recruiting
Small-Business (50 or fewer emp.)
"Saves Time and Minimizes Contract Friction"
5/5
What do you like best about Dropbox Sign (formerly HelloSign)?

I use Dropbox Sign to send out contracts to clients for review and signature, which saves me a lot of time compared to traditional methods. It minimizes the friction between my company and the client, speeding up the contract signing process. I like being able to upload contracts and expedite them quickly. The feature that allows me to save my signature and input it on contracts is really useful, saving me the time of printing, signing, and re-uploading. I also appreciate being able to track whether a contract is opened, viewed, or signed, which helps me monitor multiple contracts and know which clients to follow up with. The setup process was really easy and straightforward, and I find it simple to upload documents and send them out for signature. Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

If I was being really picky, it doesn't seem to remember my log on details. When I click remember me, I have to sign in manually each time. Review collected by and hosted on G2.com.

KP
Karthick P.
GTM Manager
Mid-Market (51-1000 emp.)
Guest users or non-business users of the software, not included in G2 scores.
"Dropbox Sign: Simple, Efficient E-Signatures with Smooth Dropbox Integration"
4/5
What do you like best about Dropbox Sign (formerly HelloSign)?

The Dropbox Sign is simple and efficient tool to make signature process easily.

Clear user interface with everything straight forward process doesn't require additional training to process

Faster document workflows with smooth drop box integration Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

There are some common downside of this tool

Limited advanced features compared to their competitors DocuSign it lack with some advanced features in workflow, complex approvals chains, conditional logic and deeper customization Review collected by and hosted on G2.com.

Nick T.
NT
Nick T.
Co-Founder | Director | Frontman
Small-Business (50 or fewer emp.)
"Fast, Great Value E-Signature Tool that's Easy to Use"
5/5
What do you like best about Dropbox Sign (formerly HelloSign)?

Fast Control Panel - Documents can be sent quickly on the move.

Set Signer Order - We ask clients to sign our agreements before we countersign

Cost - we compared HelloSign, and it came out the best value v. features Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

Nothing - the software is great and has been the best we have used Review collected by and hosted on G2.com.

Shoaib S.
SS
Shoaib S.
People and Culture Officer
Consulting
Small-Business (50 or fewer emp.)
"Efficient, User-Friendly eSignature Tool with Room for Improvement"
5/5
What do you like best about Dropbox Sign (formerly HelloSign)?

I've been using Dropbox Sign (formerly HelloSign) for around three to five years mainly for our signature needs, whether internal or client-facing documents. It's been a significant cost-saving measure, reducing the money we spend on printing. The platform is faster, simpler, and more convenient, and you don't have to be tech-savvy to use it. I really appreciate the ease of use, especially the drag-and-drop features for initials and text. Everything about it has been very efficient. I like that we're able to set queues on who gets to sign first and send signature requests in a predetermined sequence. One of the good features is the automatic reminders it sends if someone forgets to sign, and there's also the option to manually send reminders to wherever the sequence has stopped. Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

I've been requesting the feature for adding colorful stamps and signatures. I believe that customer service mentioned it's due to legal issues, but it's something we always looked forward to but never saw implemented. Also, the API feature wasn't very cost-effective for our small company; it felt a bit pricey for our needs. Review collected by and hosted on G2.com.

Verified User in Information Technology and Services
AI
Verified User in Information Technology and Services
Mid-Market (51-1000 emp.)
"Excellent Product Quick & Easy To Use!"
4.5/5
What do you like best about Dropbox Sign (formerly HelloSign)?

Easy to upload documents from various platforms, drives, drag & drop or upload directly. Can have multiple signers on one doc, various editable fields. Send a message with the doc & cc yourself or someone else. Very quick & easy to get a document out. Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

I struggled to have one doc that I could send to many, had to upload individually. Probably didnt use all the features available, maybe some 1:1 f2f/personal training when you firt sign up. ONLINE Manuals that you get referred to or docs do not cover individual experiences/user requirements. Review collected by and hosted on G2.com.

Verified User in Accounting
AA
Verified User in Accounting
Small-Business (50 or fewer emp.)
"Streamlined, Timely Document Signing with a Simple, Client-Friendly Experience"
5/5
What do you like best about Dropbox Sign (formerly HelloSign)?

It really helped streamline our workflow, and was very simple for even "less savvy" clients. Rather than waiting days or even weeks to received signed documents, most were completed within hours. Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

Sometimes if we didn't have emails for each party, we'd use the same email with different names. This sometimes caused confusion on the client end but even so, most of the time it was fairly simple. Review collected by and hosted on G2.com.

Josh M.
JM
Josh M.
CEO
Small-Business (50 or fewer emp.)
"Ok Product, horrible at scale"
0/5
What do you like best about Dropbox Sign (formerly HelloSign)?

Was easy to integrate and they give some free monthly signatures Review collected by and hosted on G2.com.

What do you dislike about Dropbox Sign (formerly HelloSign)?

Don't allow you to download your own data, without upgrading to their highest level plans. How do you not have a download all??? Bad interface, can only download one at a time, which is super slow and ineffective. Support just pushes you to upgrade, rather than help. Review collected by and hosted on G2.com.