Data checked July 11, 2026

Tailwind TMS: Pricing, Features & User Ratings

Tailwind TMS is positioned for small and midsize trucking companies and brokerages. The facts below link directly to the vendor and the identified review source.

Source disclosure: Product information comes from the vendor. The aggregate rating is a weighted average of public user ratings across independent review platforms — not a score created by Trucking Software Guide. Capterra represents the Gartner review pool (GetApp and Software Advice republish the same reviews, so we list it once), and testimonials on the vendor’s own site are excluded.

Verified at a glance

Aggregate user rating4.2/5 · 104 reviews across 4 independent platforms
Driver app rating3.7/5 · 41 app-store ratings (Google Play / App Store)
Best fitsmall and midsize trucking companies and brokerages
Pricing$99/user/month for Pro, per Capterra
Last checkedJuly 11, 2026

User ratings by platform

PlatformUser ratingReviewsSource
Capterra4.2/597View →
G25.0/51View →
SourceForge4.7/53View →
Reviews.io5.0/53View →
Google Play (driver app)3.8/537View →
Apple App Store (driver app)2.8/54View →

App-store rows measure the driver mobile app, not the full platform — they are aggregated separately as the driver app rating and never mixed into the platform score.

Published capabilities

  • Quotes, orders, dispatch and shipments
  • Receivables and payables workflows
  • Customer and vendor records
  • QuickBooks Online integration listed in third-party plan data

Pricing note

CargoWise's current Tailwind product page does not display a public starting price; Capterra lists Pro at $99 per user per month.

Primary sources

What to verify during a demo

Ask the vendor to process one representative load from order entry through dispatch, document collection, settlement and invoicing. Confirm onboarding costs, contract length, integrations, data export and every fee in writing.

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