shouldiuse.io

VERDICT

Should I use Hightail?

Simple and secure file sharing with Hightail by OpenText. Keep creative projects moving in one easy and secure cloud-based software. - hightail.com

Depends. Buy it if you're a creative team that needs client-friendly file reviews and approvals in one place. Skip it if you just need to send big files occasionally — cheaper, simpler tools do that.

Confidence

Medium. Based on ~20 public sources; most review snippets were truncated, so exact ratings and prices are partly unavailable.

Ratings

  • Value for money
  • Ease of use
  • Feature depth
  • Support quality
  • Security posture

Pricing

Free

Lite

ModelNot disclosed
Monthly feesNot disclosed
HardwareNot disclosed
Free tierYes
ProPaid (price not shown in sources)
TeamsPaid (price not shown in sources)

Best for

  • Design and video agencies
  • Client file approvals and review
  • Large video and photo delivery
  • Freelancers sharing with clients

Not for

  • Anyone just sending occasional big files
  • HIPAA-regulated healthcare (no BAAs signed)
  • Budget users — free tools cover basic sending
  • Enterprises needing managed file transfer (MFT)

Gotchas - check before you buy

high

Users report unnoticed auto-renewals and surprise paid-account charges

high

No HIPAA compliance — never send patient or regulated health data

medium

Upload caps can block large files even for regular senders

medium

Guess: Lite free tier is restrictive; real work needs paid Pro/Teams plans

Pros and cons

Pros

  • Sends large files that email can't handle
  • Built-in creative review and approval tools for client work
  • Veteran product (ex-YouSendIt), now owned by enterprise vendor OpenText
  • Free Lite tier for basic sending
  • Mobile apps available on iOS

Cons

  • PCMag rated it just 2.5/5
  • 'Stay away from the service called HIGHTAIL' forum thread over billing
  • Reddit editor blocked by upload size limits
  • Not HIPAA compliant; won't sign BAAs
  • Dedicated complaint-filing pages exist for the service

Sources & method

Analyzed 9/22/2026 - 11 sources - No known vulnerabilities found in the sources reviewed; not HIPAA compliant — Hightail won't sign BAAs.

official x2review x6security x2news x1

Key stats

  • Value for money: 2/5

    Rating

  • Free

    Starting price

  • 11

    Sources

  • Analyzed

  • Value for money: 2/5. Billing and auto-renewal complaints on forums
  • Ease of use: 3/5. PCMag calls interface merely 'useable'
  • Feature depth: 3/5. File sharing plus creative review tools
  • Support quality: 2/5. Dedicated complaint pages exist online
  • Security posture: 3/5. Encrypted per docs; not HIPAA compliant
  • 2.5/5 PCMag rating Editor review
  • Yes Free tier Lite plan
  • 1,538 Trustpilot reviews Count per Trustpilot listing
  • 2004 Founded As YouSendIt; acquired by OpenText 2018

Pricing

Lite

Free

  • Send large files
  • File previews

Pro

Paid (price not shown in sources)

  • For regular individual senders
  • Higher limits than Lite

Teams

Paid (price not shown in sources)

  • Team collaboration
  • Creative review for groups

Security

No known vulnerabilities found in the sources reviewed; not HIPAA compliant — Hightail won't sign BAAs.

What users say

Feedback is mixed: the core product is usable, but forums and Reddit flag billing surprises and upload limits.

“The interface is useable”
PCMag review
“Hightail for file upload, told me I can't upload a large file?”
Reddit, r/editors

Companies that use it

  • TPF (Australian sports agency)
  • TAIT & Associates
  • Raven5
Full analysis

Based on ~20 public sources; most review snippets were truncated, so exact ratings and prices are partly unavailable.

Fine for creative client reviews; overkill and pricier than needed for basic large-file sending.

Methodology

Based on ~20 public sources; most review snippets were truncated, so exact ratings and prices are partly unavailable.

Sources

  1. Hightail Review — PCMagpcmag.com
    review
  2. OpenText Hightail Reviews — G2g2.com
    review
  3. Trustpilot reviews of hightail.comtrustpilot.com
    review
  4. OpenText HighTail Reviews — Capterracapterra.com
    review
  5. Stay away from the service called HIGHTAIL — Creative Cowcreativecow.net
    review
  6. Hightail upload limit complaint — Reddit r/editorsreddit.com
    review
  7. Is Hightail HIPAA compliant? — Pauboxpaubox.com
    security
  8. Hightail Security Rating — UpGuardupguard.com
    security
  9. Plans & Pricing — Hightailhightail.com
    official
  10. Creative collaboration — Hightailhightail.com
    official
  11. OpenText Acquires Hightailopentext.com
    news

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