---
title: "Tailwind TMS Software Pricing, Alternatives & More 2026 | Capterra"
description: "With the help of Capterra, learn about Tailwind TMS Software - reviews, pricing plans, popular comparisons to other Transportation Management products and more."
source_url: "https://www.capterra.com/p/275384/Tailwind-TMS/"
page_type: "product"
language: "en"
---

# 

 Tailwind TMS Software Review 2026: Features, Integrations, Pros & Cons

Last updated on August 3, 2026

Provider data verified by our Software Research team, and reviews moderated by our Reviews Verification team.

[Description](#description)[Use cases](#use-cases)[Alternatives](#alternatives)[FAQs](#faqs)[Features](#features)[Pricing](#pricing)[Integrations](#integrations)[Support](#support)[Reviews](#reviews)

Tailwind TMS

## What is Tailwind TMS?

Award winning web-based transportation management software. No set-up fees. No contracts. Free trial. Tailwind's all-in-one TMS improves cash-flow & profits for small to mid-sized trucking companies, freight brokerages, and those that do both. Compete with the big guys - starting at just $99/month. Tailwind helps manage operations, customers, dispatch, admin & accounting. Also includes the free 'POD Complete' trucking app (Android & iPhone).

## What is Tailwind TMS used for?

[Transportation Dispatch](https://www.capterra.com/transportation-dispatch-software/)[Logistics](https://www.capterra.com/logistics-software/)[Transportation Management](https://www.capterra.com/transportation-management-software/)

Top alternative

Featured

Overall rating

Based on 97 user reviews

Reviews sentiment

Positive

84%

Neutral

10%

Negative

6%

Starting price

$99

Per User, Per Month

Free trial  
available

Free version not included

Capterra Shortlist charts the highest-rated and most popular products...

Our "Best of" badge program showcases products with the highest ratings...

Our "Best of" badge program showcases products with the highest ratings...

Do you work for Tailwind TMS?[Manage this product listing](https://digitalmarkets.gartner.com/get-listed/claim-bx?url=https://www.envasetechnologies.com/&name=Tailwind TMS)

## Compare with a popular alternative

Capterra selects software alternatives based on relevant features, verified user reviews and user interactions. Placement may be influenced by client status.

### Tailwind TMS

4.2 (97)

VS.

[4.2 (244)](https://www.capterra.com/p/29249/Express/reviews/)

Starting Price

$99

Per User, Per Month

Starting Price

Contact vendor

Free Trial

Free Version

Pricing Options

Free Trial

Free Version

Ease Of Use

4.2 (97)

Ease Of Use

4.2 (1,018)

Value For Money

4.2 (61)

Value For Money

4.0 (953)

Customer Service

4.5 (96)

Customer Service

4.2 (963)

## Tailwind TMS alternatives

Highest Rated

[4.7 (743)](https://www.capterra.com/p/136895/Freightview/reviews/)

Starting price

$149.00

Per User, Per Month

Pricing Options

Free Trial

Free Version

User Rating

97%

of reviewers

rated it above 4 stars

[4.7 (388)](https://www.capterra.com/p/131389/Elite-EXTRA/reviews/)

Starting price

$24.00

Per User, Per Month

Pricing Options

Free Trial

Free Version

User Rating

97%

of reviewers

rated it above 4 stars

[4.7 (108)](https://www.capterra.com/p/239697/MyCarrier/reviews/)

Starting price

$60.00

Per User, Per Month

Pricing Options

Free Trial

Free Version

User Rating

97%

of reviewers

rated it above 4 stars

[4.4 (51)](https://www.capterra.com/p/249961/Alvys-TMS/reviews/)

Starting price

$500.00

Per User, Per Month

Pricing Options

Free Trial

Free Version

User Rating

82%

of reviewers

rated it above 4 stars

[View all alternatives](https://www.capterra.com/p/275384/Tailwind-TMS/alternatives/)

## FAQs about Tailwind TMS

Overview

### What problems does Tailwind TMS solve?

Tailwind TMS solves time-consuming dispatch, load tracking, invoicing, and driver settlement workflows by centralizing orders, equipment, customer records, and accounting in one system. Dispatchers, brokers, accountants, and small carrier teams use it to reduce paperwork, avoid duplicate data entry, speed onboarding, improve shipment visibility, and handle support issues quickly.

Answer based on 76 reviews

Overview

### Which roles and teams benefit most from Tailwind TMS?

Tailwind TMS is most used by transportation business owners, presidents, and executives who need visibility into fleet performance, profitability, and daily operations. Operations managers, dispatchers, and office teams rely on it to manage loads, scheduling, and customer communication, while accountants and controllers use it for invoicing, settlements, and financial tracking.

Answer based on 94 reviews

Overview

### What company size and industries is Tailwind TMS built for?

Tailwind TMS is built for growing small OTR trucking companies and freight brokerages, with 97% of reviewers from small businesses. It primarily serves Transportation/Trucking/Railroad companies at 78%, followed by Logistics and Supply Chain at 16%, with limited use outside those sectors.

Answer based on 97 reviews

Features and Usability

### What are the key features of Tailwind TMS?

Tailwind TMS includes core transportation features like dispatch management, order management, shipment tracking, and billing and invoicing. Differentiating capabilities include EDI, equipment maintenance, and a mobile app for POD and driver updates. Commonly cited functions also cover accounting, driver settlements, reporting, and QuickBooks integration.

Answer based on 53 reviews

Pricing

### How much does it cost and what fees or limitations are included?

Tailwind TMS starts at $99/user/month for Pro, with Enterprise at 149 and Unlimited at 199; all plans include a free trial. Reviewers often call it affordable with no upfront fee, but some say extra users are costly and smaller companies may find it expensive. Pro includes 25 loads/month.

Answer based on 13 reviews

Integrations

### Which third-party tools and platforms does Tailwind TMS integrate with?

Tailwind TMS connects natively to Descartes MacroPoint, EZCheck-In, EZTrack, FleetOne, Google Maps, Kleinschmidt, QuickBooks Online Advanced, and Samsara. These integrations cover tracking, check-in, mapping, accounting, and fleet data connections within one TMS environment.

Answer based on 6 reviews

Getting Started and Support

### How easy is it to onboard and train a team on Tailwind TMS?

Tailwind TMS is generally easy to onboard, with in-person training, live online sessions, webinars, documentation, and videos available. Reviewers say dispatchers, small teams, and users with limited computer skills get productive quickly, while some admins or new users need several weeks to fully understand reports, workflows, and broader system setup.

Answer based on 31 reviews

Getting Started and Support

### What customer support options does Tailwind TMS offer, and how do users rate the experience?

Tailwind TMS offers email/help desk, FAQ/forum, knowledge base, phone support, 24/7 live representatives, and chat. Users often describe support as fast, hands-on, and easy to understand, with helpful training resources. Some report frustrations after platform changes, including slower responses, portal reliance, and uneven follow-through on requests.

Answer based on 53 reviews

Accounting and tracking

### How well does Tailwind TMS handle accounting and load tracking?

Tailwind TMS handles day-to-day load tracking and core accounting tasks well for many trucking and brokerage teams. It supports dispatch, invoicing, payables, receivables, reporting, and order visibility in one system, though some users find accounting workflows less flexible and want stronger reporting, audit history, and outside software integrations.

Answer based on 24 reviews

## Features

AI summary

Based on 947 Transportation Management reviews

Capterra reviewers highlight these as the top features buyers look for in transportation dispatch software:

-   **Dispatch Management** (**58%** of reviewers rated this feature as critical)
-   **Delivery Tracking** (**58%**)
-   **Billing & Invoicing** (**59%**)

Tailwind TMS includes **Dispatch Management** and **Billing & Invoicing**, giving teams the tools to assign loads efficiently and handle customer billing from the same system. However, it does not include **Delivery Tracking**. Instead, it offers **GPS** (**53%**), which can help dispatchers monitor vehicle locations and stay informed on route activity. Together, these features help businesses coordinate daily operations, manage payments accurately, and keep teams informed while freight is in motion.

Dispatch Management

3.0 (1)

0.00% of 1 reviewers that rated this feature as important or highly important

Manage sending personnel and resources to a site as needed

Billing & Invoicing

4.3 (4)

75.00% of 4 reviewers that rated this feature as important or highly important

Create, manage, and send invoices or bills to customers

GPS

3.0 (1)

0.00% of 1 reviewers that rated this feature as important or highly important

System to support the positioning, navigation, and timing (PNT) measurements of an object or individual

Order Management

3.6 (5)

100.00% of 5 reviewers that rated this feature as important or highly important

Manage and track customer orders for goods, investments, or any other purchases

3PL Management

4.7 (3)

100.00% of 3 reviewers that rated this feature as important or highly important

Outsource and manage third party logistics

Scheduling

3.7 (3)

66.67% of 3 reviewers that rated this feature as important or highly important

Plan availability and assign specific time slots for tasks and resources

Tailwind TMS 47 features

### All Features
- 3PL Management: Outsource and manage third party logistics
- Accounting: Built-in accounting to manage ledger, accounts payable/receivable, financial reports, etc.
- API: Application programming interface that allows for integration with other systems/databases
- Billing & Invoicing: Create, manage, and send invoices or bills to customers
- Carrier Management: Find, compare, and select the most time/cost-effective freight carrier
- Communication Management: Manage and track all internal and external communication conducted via calls, email, text, or chat
- Contact Database: Centralized database of stakeholders and their contact information such as names, address, phone number etc.
- CRM: Built-in customer relationship management (CRM) capabilities or integration with a third-party CRM system
- Customer Database: A collection of customer information such as contact details, demographics, previous interactions, etc.
- Customer Management: Store and organize information about customers and previous interactions
- Customer Portal: A website or login for customers to access information
- Data Import/Export: Import and export data to and from software applications
- Dispatch Management: Manage sending personnel and resources to a site as needed
- Driver Management: Track all personnel who operate company vehicles
- Driver Settlements: Manage payroll processing for different driver pay contracts
- EDI: Transfer of data from one computer system to another
- Fleet Management: Management of commercial motor vehicles for work-related purposes
- For Freight Operations: Intended to be used by freight brokers and logistics companies
- Fuel Management: Monitor fuel consumption and optimize fuel usage
- GPS: System to support the positioning, navigation, and timing (PNT) measurements of an object or individual
- Historical Reporting: Information, data and reports that are being tracked over time
- Import/Export Management: Management of inbound and outbound shipments in the context of international trade
- International Forwarders: Freight forwarder/forwarding agent that transports cargo internationally with knowledge of customs, and international boundaries, etc.
- Live Driver Tracking: Track driver locations on a map in real time
- Load Optimization: Set up process for efficient load building, routing, and distribution
- Local Forwarders: Freight forwarder/forwarding agent that transports cargo domestically with specialized knowledge of local logistics services
- LTL/Shared Truckload: Trucks that do not reach full load and can be shared
- Maintenance Management: Manage, maintain and track the performance of assets and equipment
- Maintenance Scheduling: Schedule predetermined or ad hoc maintenance services and labor requests
- Mileage Tracking: Log miles driven for tax deduction or reimbursement purposes
- Mobile App: Access the system via a mobile application
- Order Management: Manage and track customer orders for goods, investments, or any other purchases
- Order Tracking: Track orders throughout the fulfillment process
- QuickBooks Integration: Integrates with QuickBooks
- Quotes/Estimates: Generate quotes or estimates for customers
- Rate Management: Track/optimize rates in relation to usage
- Real-Time Notifications: Notifications that are delivered to users as soon as an event occurs
- Reporting/Analytics: View and track pertinent metrics to find patterns and gain insights from data
- Routing: Plan daily routes to optimize employee scheduling and provide directions
- Scheduling: Plan availability and assign specific time slots for tasks and resources
- Shipment Tracking: The software will assign a tracking number associated to the order number to track the physical progress of the package in delivery.
- Third-Party Integrations: Set up connections to third-party platforms to improve business processes
- Transportation Management: Organize and track the physical movement of goods from one location to another
- Trip Logs: Record of trip details
- Truckload Management: Track and manage transportation of large cargo that fills an entire trailer/truck
- Vehicle Management: Track and monitor how vehicles are used
- Waybills: Official shipping document that identifies origin and destination of the shipment, weight, freight, and other details of goods

---

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Features

4.0 (69)

4.0

Based on 69 reviews

## Pricing

Value for money

4.2 (61)

Free Trial

[View pricing plan details](https://www.capterra.com/p/275384/Tailwind-TMS/pricing/)

Pro

$99.00

Per User,Per Month

It includes:

-   25 Loads/Month GPS Confirmed Shipment and Event Tracking
-   Accounting & Operations Report
-   Account Receivable Management
-   Accounts Payable Management
-   Admin
-   Businner Document Customization
-   Claims.Accident/Incident Tracking
-   Complete Quote and Order System
-   Customer and Carrier History
-   Customer and Vendor Database
-   Custom User Security
-   Direct Emailing From TMS
-   Dispatch and Shipment Tracking System
-   Equipment Maintenance Tracking
-   Factor Support
-   Fuel Bill Importing
-   Location and Route Management
-   Macropoint Shipment Tracking Integration
-   Mileage Calculations
-   Multi-Branch Management
-   POD Import and Attach
-   Print Checks Right From the TMS
-   Quickbooks Online Sync
-   Saferwatch FMCSA Data Feed
-   Sales Commission System
-   Support US and CDN Currencies
-   Task and Alert Notification System

Enterprise

$149.00

Per User,Per Month

It includes:

-   50 Loads/Month GPS Confirmed Shipment and Event Tracking
-   API Access for Tailwind Supported Integrations
-   Carrier Self-Service Portal
-   Customer Self-Service Portal
-   Electric Load/ Rate Confirmation and Acceptance
-   Samsara ELD Integration

Unlimited

$199.00

Per User,Per Month

It includes:

-   API Web-Hooks for Self-Serve Integrations
-   Custom Reporting and Analytics With Power BI Integration
-   Easy Carrier Onboarding With RIMS Integration
-   Unlimited Loads GPS Confirmed Shipment and Event Tracking

Value for money

4.2 (61)

4.2

Based on 61 reviews

## Integrations

[

Google Maps](https://www.capterra.com/p/227511/Google-Maps/)[

QuickBooks Online Advanced](https://www.capterra.com/p/189398/QuickBooks-Online/)[

Samsara](https://www.capterra.com/p/167543/Samsara-for-Fleets-0-00-6-23/)[

Descartes MacroPoint](https://www.capterra.com/p/219845/Descartes-MacroPoint/)[

Kleinschmidt](https://www.capterra.com/p/183675/Kleinschmidt-EDI-Integration/)[

EZCheck-In](https://www.capterra.com/p/228664/EZCheck-In/)[

EZTrack](https://www.capterra.com/p/228662/EZTrack/)

Connect with a Capterra advisor for a free 15-minute consultation

Get a personalized software list aligned to your business needs with guidance from our expert advisors. Our team has helped 1 million+ businesses like yours find options that fit their needs.

## Support, customer service and training options

Customer Service

4.5 (96)

Support

-   Email/Help Desk
-   FAQs/Forum
-   Knowledge Base
-   Phone Support
-   24/7 (Live rep)
-   Chat

Training

-   In Person
-   Live Online
-   Webinars
-   Documentation
-   Videos

Deployment

-   Web
-   Android
-   iPhone/iPad

Typical users

-   Freelancers
-   Small businesses
-   Mid size businesses
-   Enterprises

Customer Service

4.5 (96)

4.5

Based on 96 reviews

## User reviews

Overall rating

4.2

Based on 97 reviews

Filter by rating

5(50)

4(31)

3(10)

2(2)

1(4)

Mentioned topic

Sorted by most recent

Francois D.

President

Logistics and Supply Chain

### "Do not recommend"

1.0

Overall Rating

1.0

1.0

Ease of Use

4.0

4.0

Features

3.0

3.0

Customer Service

1.0

1.0

Likelihood to Recommend

0/10

August 28, 2025

Pros

Friendly user, easy setup, cloud based TMS system. Clean and effective system. Easy to use and train new staff to use.

Cons

Ever since Tailwind was sold to a US based company, the support is almost unexistent. We sometimes have to wait over 24 hrs only to get an answer, sometimes up to a week to get resolution. As an example, Vendor pay list has not been working for 48hrs, therefore unable to pay my carriers. Very frustrating. Planning to change to another TMS system very soon.

Review source

Non-incentivized review: any software user can leave a review for any product listed on our site. All submitted reviews are subject to our verification process prior to publication.

M-

Martin - John S.

Operation - Dispatch Lead

Logistics and Supply Chain

### "Operation Manger and lead dispatch "

1.0

Overall Rating

1.0

1.0

Ease of Use

1.0

1.0

Features

2.0

2.0

Customer Service

1.0

1.0

Likelihood to Recommend

0/10

December 11, 2024

Originally hey this is pretty good but since there so called update or new platform its gone to crap. Getting service is terrible def wouldn't recommend it to anyone anymore

Pros

Originally pricing was decent and they had great customer service till platform changed here around October or so now its just crap save yourself the headaches avoid product

Cons

Customer service is almost non existent they want you to go to a \[portal now set up a account and send in requests for service that way. Terrible option took a decent product right down to crapper when they did this. Its stalling more and more and we have to refresh 15-20 times a day just always waiting for it to go to next step very slow.

Review source

Non-incentivized review: any software user can leave a review for any product listed on our site. All submitted reviews are subject to our verification process prior to publication.

AK

Ashveen K.

Dispatcher

Transportation/Trucking/Railroad

### "Review for TAILWIND TMS"

5.0

Overall Rating

5.0

5.0

Ease of Use

5.0

5.0

Features

5.0

5.0

Customer Service

5.0

5.0

Likelihood to Recommend

10/10

August 29, 2022

Very satisfactory and easy to navigate around

Pros

Easy to find an order and create a dispatch and save the POD and BOL and enter the cost associated with the load

Cons

Based on the internet connection sometimes it slow to load the information on the page or top open a file

Review source

Vendor Referred - Incentive Offered: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you.

Response from Vendor

September 6, 2022

Hi Ashveen, thank you for your review and feedback. It's great to hear that Tailwind has made dispatching an easier and seamless process for you! Our development team is always working to improve the user experience, so even though internet speed is out of our hands, we will keep an eye on the backend to see if there is anything we can do to improve page load speed :)

MB

Mario B.

Operations Manager

Transportation/Trucking/Railroad

### "Good Product, but too expensive"

3.0

Overall Rating

3.0

3.0

Ease of Use

4.0

4.0

Features

3.0

3.0

Customer Service

3.0

3.0

Likelihood to Recommend

1/10

July 5, 2022

Pros

The Product is an easy-to-use TMS and I've used others similar in the past. It does what it's suppose to do though. Their CS team is decent.

Cons

Too expensive, software doesn't support the price. Many others do the same thing for far less, and with better customer service. Their CS team is decent, although could be more knowledgeable on the product itself.

Review source

Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication.

JS

Jamil S.

President

Transportation/Trucking/Railroad

### "Best TMS for the Money"

5.0

Overall Rating

5.0

5.0

Ease of Use

5.0

5.0

Features

5.0

5.0

Customer Service

5.0

5.0

Likelihood to Recommend

10/10

February 25, 2022

Great support team, helped immidiatly

Pros

Easy to use, does everything we need it to do

Cons

ALl is well, nothing bad that I can think of

Review source

Vendor Referred: This reviewer was invited by the software vendor to submit an honest review.

Response from Vendor

August 25, 2022

Thanks for your feedback, Jamil! We are very pleased to hear that Tailwind met all of your needs and helped your business grow. Our team works hard to provide the best support and guidance in each interaction, so we are glad you have enjoyed your experiences and that we provided the help you needed promptly.

PC

Patty C.

AccountingSpecialist

Transportation/Trucking/Railroad

### "Bad "

1.0

Overall Rating

1.0

1.0

Ease of Use

2.0

2.0

Features

2.0

2.0

Customer Service

0.0

0.0

Likelihood to Recommend

0/10

January 4, 2022

Pros

There is nothing that I really like about this software.

Cons

I have to size ALL my paperwork because of the transmissions fail on most every single one that has to be sent to customer. Also there is no way to see if the invoice sent. It states that it was sent but a lot of the times it does not make it to the customer.

Review source

Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication.

Response from Vendor

January 25, 2022

Hi Patty, Thank you for your feedback. I'm not sure why your specific transmissions may be failing, but I have let our support and tech team know and they are investigating. If you can further elaborate using the in-app chat within the Tailwind TMS we may be able to get to the bottom of it faster!

AD

Audrey D.

Manager

Transportation/Trucking/Railroad

### "Worthy of managing your transportation needs"

5.0

Overall Rating

5.0

5.0

Ease of Use

5.0

5.0

Features

5.0

5.0

Customer Service

5.0

5.0

Likelihood to Recommend

7/10

January 4, 2022

Automated BOLs - I have been working manually so long this is a small but necessary function.

Pros

I like the ease of use. I have been able to train people remotely which is necessary at this time. Anyone I train seems to manage navigating it with ease.

Cons

Nothing I can think of - it works fine for the functions I require of it.

Reasons for choosing Tailwind TMS

We liked the product and the pricing was mid range.

Review source

Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication.

Response from Vendor

August 25, 2022

Audrey, thank you for your detailed review of Tailwind! After more than two years with us, your high marks across the board carry a lot of significance. It is great to know that you have found the platform to be very intuitive, and are able to easily onboard new employees as you scale your company. We are so glad that Tailwind was the right fit for your business, and we look forward to growing with you every step of the way!

NC

Nick C.

Vice President

Logistics and Supply Chain

### "tailwind"

4.0

Overall Rating

4.0

4.0

Ease of Use

4.0

4.0

Features

4.0

4.0

Customer Service

4.0

4.0

Likelihood to Recommend

10/10

January 4, 2022

so far so good. Would keep this product

Pros

Very easy to build out and manage loads. The support is very good as well.

Cons

The accounting is a bit difficult along with multi stop trips

Review source

Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication.

MB

Morgan B.

logistics coordinator

Transportation/Trucking/Railroad

### "good"

4.0

Overall Rating

4.0

4.0

Ease of Use

4.0

4.0

Features

3.0

3.0

Customer Service

4.0

4.0

Likelihood to Recommend

6/10

January 4, 2022

Pros

dispatch. customer and carrier records.

Cons

Many times makes me log in every time I click on a new page.

Review source

Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication.

PS

Paul S.

Owner

Logistics and Supply Chain

### "End User"

4.0

Overall Rating

4.0

4.0

Ease of Use

5.0

5.0

Features

4.0

4.0

Customer Service

5.0

5.0

Likelihood to Recommend

7/10

December 29, 2021

Pros

The software is straight forward and easy to use.

Cons

Not enough customization is available. There are a few features that I would like to be able to customize, that I am not able to.

Review source

Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication.

[View all Reviews](https://www.capterra.com/p/275384/Tailwind-TMS/reviews/)

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Popular comparisons

[Samsara vs Tailwind TMS](https://www.capterra.com/compare/167543-275384/Samsara-for-Fleets-0-00-6-23-vs-Tailwind-TMS)