Dropbox vs ShareFile (2026): which should you pick?

Pick Dropbox if

• Fits if you want 2 TB that syncs across Windows, Mac and Linux
• Works for people who send big files to clients, with transfers of up to 50 GB on Plus

Look elsewhere if

• Tight if you're staying free, because Basic stops at 2 GB
• Pricey if you only need a few hundred GB, as the smallest paid plan is 2 TB at $9.99 a month, the dear end of this category
• Skip it if you want end-to-end encryption for yourself, since it's on Advanced, which needs 3 people
• Watch out: monthly billing costs more, $11.99 for Plus and $18 a user for Standard
• Watch out: there's no trial of Plus, and reviewers say reaching a real person in support is hard

Pick ShareFile if

• Fits if you send documents to clients and want portals and tracking
• Works for a firm of 3 or more with a compliance need on the Premium plan

Look elsewhere if

• Pricey if you're alone: every plan needs at least 3 users
• Skip it if you want a free plan, as there is none
• Tight if you need e-signatures or forms, which start at Premium at $26 a user
• Watch out: storage starts at 3 TB for the whole account, with more in 3 TB packs

Dropbox

• The free Basic plan includes only 2 GB of storage.
• The cheapest paid plan is Plus at 2 TB for one person; the plans page lists no smaller paid tier.
• End-to-end encryption, single sign-on and audit logs are limited to Advanced, which requires at least 3 users.
• Monthly billing costs more: $11.99 for Plus and $18 per user for Standard, against $9.99 and $15 on yearly billing.

ShareFile

• No free plan, and each plan needs at least 3 users.
• Plans start with 3 TB of account storage in total; more comes in 3 TB packs.
• E-signatures, forms, workflow automation and HIPAA, FINRA and SEC support start at Premium.
• The pricing page mentions desktop and mobile apps without naming operating systems, so only web is listed.

Dropbox

Sync across devices

Files stay in sync between the desktop apps, the mobile apps and the web, and every paid plan allows an unlimited number of connected devices.

File recovery and version history

Deleted files and earlier versions can be restored for 30 days on Plus, 180 days on Standard and 1 year on Advanced.

Large file transfers

Send a copy of files by link: up to 50 GB per transfer on Plus and up to 100 GB on Standard and Advanced, where transfers can also be password protected.

PDF editing and signatures

Edit, annotate and sign PDFs inside Dropbox. The paid plans list unlimited self-signing and 3 signature requests per month.

Team folders and admin console

Standard adds team-owned folders, groups and an admin console. Advanced adds tiered admin roles, audit logs with file event tracking and single sign-on.

Connections to AI tools

Dropbox content can be connected to AI tools such as ChatGPT, Claude and Gemini to find and summarize files and save work back to Dropbox.

ShareFile

Encrypted sharing

Files are stored encrypted and shared by link, with link expiration dates and remote lock and wipe for lost devices.

Client portal

Clients get a branded place to receive and upload files. Unlimited client users are included on every plan.

Requests, forms and e-signatures

Premium and above can collect documents, forms and signatures from clients and route them through automated workflows.

Email add-ins

Integrations for Outlook, Outlook Online and Gmail replace attachments with secure ShareFile links.

Access and security controls

Multi-factor sign-in, Active Directory single sign-on, activity reports and file-level permissions. Enterprise adds provisioning and monitoring.

Dropbox

• Basic$0

  2 GB to store and share files.

• Plus$9.99

  per month, billed yearly ($11.99 billed monthly)

  For 1 person: 2 TB of storage, 30 days to restore deleted files and transfers of up to 50 GB.

• Standard$15

  per user / month, billed yearly ($18 billed monthly)

  For 1 person or more: storage starts at 3 TB for the team, 180-day restore, 100 GB transfers, team folders and admin controls.

• Advanced$24

  per user / month, billed yearly ($30 billed monthly)

  For 3 people or more: storage starts at 15 TB, 1-year restore, end-to-end encryption, single sign-on and tiered admin roles.

• EnterpriseCustom

  Custom pricing with integrations for third-party security tools and live support from dedicated staff.

ShareFile

• Advanced$16.50

  per user / month, billed annually ($18.15 billed monthly)

  Encrypted storage and sharing, real-time co-editing, access controls and basic reporting. 3-user minimum.

• Premium$26.00

  per user / month, billed annually ($28.59 billed monthly)

  Adds e-signatures, requests, forms, workflow automation, an enhanced client portal and AI document automation. 3-user minimum.

• Enterprise$35.00

  per user / month, billed annually ($42.00 billed monthly)

  Adds automated user provisioning, data loss protection and security monitoring tools. 3-user minimum.

• Virtual Data Room$69.30

  per user / month, billed annually ($77.00 billed monthly)

  Confidential document sharing with granular access for deals and audits. 1 GB storage per license, 5-license minimum.

Dropbox

• Annual discount

  About 17% to 20% lower with yearly billing

  Billed yearly, Plus is $9.99 a month instead of $11.99, Standard is $15 per user instead of $18, and Advanced is $24 per user instead of $30.

ShareFile

No public discounts listed.