Tailwind TMS review: features, pricing & user reviews
Carrier and brokerage TMS with document AI and accounting features; now part of WiseTech's CargoWise.
Features checked Sep 2026 · Pricing checked Oct 2026 · Reviews analyzed through Sep 2026
Tailwind TMS is a trucking management system for small fleets (3–10), growing fleets (10–50) and brokers. It fully offers 19 of 34 features and 6 partially. It does not publish a price for 3 trucks, and 37% of 42 public reviews are positive. Checked Sep 2026.
Strengths
- Has bol / pod capture (only 5 of 20 tools document it)
- Has vendor bills (ap) (only 6 of 20 tools document it)
- Has safety management (only 3 of 20 tools document it)
- Users praise support (2 positive mentions)
- Users praise price/value (2 positive mentions)
Watch-outs
- Profit per load / truck: not documented publicly (most tools have it)
- IFTA reporting: not documented publicly (most tools have it)
- Users complain about missing feature/request (4 negative mentions)
- Users complain about support (3 negative mentions)
- No public pricing; requires a sales call
Features
Loads & dispatch
?Rate con auto-importUnclear
Only e-rate-confirmation send/accept; no inbound RC OCR evidenced
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on rate con auto-import →?Revised rate con trackingUnclear
No revised-RC/versioning evidence
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on revised rate con tracking →✓Dispatch boardOffered
Dispatch management + scheduling; board UI detail not evidenced
“Dispatch & Shipment Tracking System”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on dispatch board →✓Driver assignment & dispatch sendOffered
Dispatch comms to drivers via app
“a free mobile ePOD capture and dispatch communications app (Tailwind POD Complete)”
Source: www.getapp.ae · Vendor claim · checked Sep 2026
Compare all tools on driver assignment & dispatch send →◐Chat-based intake (no app install)Partial
SMS messaging listed; no doc intake over SMS evidenced
“SMS Text Messaging”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on chat-based intake (no app install) →✓Load board integrationOffered
Posting-oriented; reviewer says load board integrations lacking
“post their freight brokerage on multiple load boards such as Post Everywhere, DAT Solutions, Truckstop.com”
Source: www.getapp.ae · Third-party source · checked Sep 2026
Compare all tools on load board integration →✓Mileage & routingOffered
Mileage calculations + HERE
“The product is integrated with Here.com for route and load optimization.”
Source: www.getapp.ae · Third-party source · checked Sep 2026
Compare all tools on mileage & routing →?Detention & accessorialsUnclear
No detention/accessorial evidence
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on detention & accessorials →?Facility insightsUnclear
Only "Locations and Route Management" records listed; no facility intelligence evidenced
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on facility insights →Drivers & paperwork
✓Driver mobile appOffered
Free for drivers on all tiers
“Tailwind POD Complete, the essential phone application compatible with both iPhone and Android devices”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on driver mobile app →✓BOL / POD captureOffered
Capture; validation not evidenced. Reviewer: file format/size issues
“empowers drivers to capture signed Bills of Lading (BOLs), and easily submit Proof of Deliveries (PODs)”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on bol / pod capture →✓Document libraryOffered
“Centralize your paperwork No more searching for lost documents.”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on document library →Tracking & fleet
◐ELD / GPS trackingPartial
Samsara on Enterprise+; GPS-tracked loads capped per tier (25/50/unlimited); reviewer cites lacking ELD integrations
“Samsara ELD Integration”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on eld / gps tracking →✓MaintenanceOffered
“Equipment Maintenance Tracking”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on maintenance →◐Equipment registryPartial
Directory feature checkbox + equipment maintenance
“Fleet Management”
Source: www.softwareadvice.com · Third-party source · checked Sep 2026
Compare all tools on equipment registry →Billing & accounting
✓Customer invoicingOffered
“Handle quotes, orders, bills of lading, load confirmations, invoices and settlements”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on customer invoicing →◐Factoring integrationPartial
Packet export only; no factor API integration evidenced
“You can easly export documenta as 1 file for your factoring.”
Source: www.softwareadvice.com · Third-party source · checked Sep 2026
Compare all tools on factoring integration →✓Driver settlementsOffered
“Driver/Carrier Settlements”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on driver settlements →◐PayrollPartial
Reviewer mentions payroll; another reviewer says payroll complicated
“It has a lot of bells and whistles which we find are useful, from payroll to Quickbooks integration.”
Source: www.getapp.ae · Third-party source · checked Sep 2026
Compare all tools on payroll →✓QuickBooks integrationOffered
All tiers
“QuickBooks Online Sync (requires QuickBooks Online Plus or higher)”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on quickbooks integration →✓Expenses & fuel cardsOffered
“Fuel Bill Importing”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on expenses & fuel cards →✓Vendor bills (AP)Offered
Plus print checks from TMS
“Accounts Receivable & Payable Management”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on vendor bills (ap) →?General ledgerUnclear
No native GL evidenced; relies on QBO sync
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on general ledger →?Profit per load / truckUnclear
No per-load/truck profitability evidence
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on profit per load / truck →Compliance & safety
?IFTA reportingUnclear
Mileage + fuel import listed; IFTA report not evidenced in fetched pages
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on ifta reporting →◐Driver qualification filesPartial
Carrier FMCSA monitoring; driver DQ file not evidenced here
“SaferWatch FMCSA Data Feed”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on driver qualification files →✓Safety managementOffered
“Claims/Incidents/Accident Tracking”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on safety management →Platform & AI
✓Reports & analyticsOffered
Custom/Power BI on Unlimited; preset reports on Pro
“Custom Reporting and Analytics with Power BI Integration”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on reports & analytics →✓CRM & broker creditOffered
Credit checks not evidenced
“Customer and Vendor Database”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on crm & broker credit →?AI assistantUnclear
No AI feature evidenced
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on ai assistant →?Roles & permissionsUnclear
No roles/permissions evidence found
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on roles & permissions →✓Customer portalOffered
Enterprise tier+
“Customer Self-Service Portal – made available through your website”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on customer portal →✓Open API & integrationsOffered
API on Enterprise; webhooks/EDI on Unlimited
“API Web-Hooks for self-serve integrations”
Source: www.cargowise.com · Vendor claim · checked Sep 2026
Compare all tools on open api & integrations →✓Public pricing & self-serveOffered
Published tiers + free trial (directory); vendor site tailwindtms.com dead
“Tailwind Pro costs $99 user/month, and Tailwind Enterprise - $149 user/month, and Tailwind Unlimited, $199 user/month.”
Source: www.getapp.ae · Third-party source · checked Sep 2026
Compare all tools on public pricing & self-serve →Pricing
Model: Per user · Trial: Yes
| Plan | Monthly | Annual (per mo) | Billed by | Trial | Source |
|---|---|---|---|---|---|
| Unlimited (vendor checkout page) | — | — | user | 3-month trial | vendor page Oct 2026 |
| Pro (directory figure, 2026-09-26) | $99 | — | user | — | directory Sep 2026 |
What users say
42 public reviews from softwareadvice (36), appstore (4), capterra (2). 6 published in 2024 or later. Reviews may cover the vendor’s wider product family.
Most praised
- support2
- price/value2
- invoicing/payment2
- doc/photo capture2
“Other simular solutions charge 7-25,000$ Down payment and 800-1300 a month.”
“You can easly export documenta as 1 file for your factoring.”
“Great reports, and you can store files on trucks, drivers, and all your exp data.”
Most criticized
- missing feature/request4
- support3
- price/value3
- reliability/bugs3
“Ever since Tailwind was sold to a US based company, the support is almost unexistent.”
“Tailwind glitches sometimes, which can be frustrating to deal with.”
“I don't like AI-generated content, so I haven't used their ghostwriter feature (ten credits per month).”
Third-party ratings (Sep 2026): Capterra: 4.2–4.3/5, 97 reviews; G2: 5/5, 1 review
Tailwind TMS alternatives
All Tailwind TMS alternatives
FAQ
How much does Tailwind TMS cost?
Tailwind TMS does not publish a complete price list; pricing is per user.
Does Tailwind TMS have quickbooks integration?
Offered. All tiers
Does Tailwind TMS have driver mobile app?
Offered. Free for drivers on all tiers
Does Tailwind TMS have rate con auto-import?
Not documented publicly. Only e-rate-confirmation send/accept; no inbound RC OCR evidenced
Does Tailwind TMS have ifta reporting?
Not documented publicly. Mileage + fuel import listed; IFTA report not evidenced in fetched pages