# Tailwind TMS Software Pricing, Alternatives & More 2026 | Capterra

> With the help of Capterra, learn about Tailwind TMS Software - reviews, pricing plans, popular comparisons to other Transportation Management products and more.

Source: https://www.capterra.com/p/275384/Tailwind-TMS

---

# 

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

Last updated on March 13, 2026

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[Description](#description)[Use cases](#use-cases)[Alternatives](#alternatives)[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

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.

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

Starting Price

$99

Per User, Per Month

Starting Price

$24

Per User, Per Month

Free Trial

Free Version

Pricing Options

Free Trial

Free Version

Ease Of Use

4.2 (97)

Ease Of Use

4.5 (356)

Value For Money

4.2 (61)

Value For Money

4.6 (321)

Customer Service

4.5 (96)

Customer Service

4.8 (341)

## Tailwind TMS alternatives

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

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

Starting price

Contact vendor for pricing

Pricing Options

Free Trial

Free Version

User Rating

90%

of reviewers

rated it above 4 stars

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

[Motive](https://www.capterra.com/p/138669/Motive/)

[4.5 (1,687)](https://www.capterra.com/p/138669/Motive/reviews/)

Starting price

Contact vendor for pricing

Pricing Options

Free Trial

Free Version

User Rating

89%

of reviewers

rated it above 4 stars

[Learn More](https://www.capterra.com/p/138669/Motive/)

Highest Rated

[One Step GPS](https://www.capterra.com/p/197399/One-Step-GPS/)

[4.8 (262)](https://www.capterra.com/p/197399/One-Step-GPS/reviews/)

Starting price

$13.95

Per User, Per Month

Pricing Options

Free Trial

Free Version

User Rating

98%

of reviewers

rated it above 4 stars

[Learn More](https://www.capterra.com/p/197399/One-Step-GPS/)

[PCS TMS](https://www.capterra.com/p/29249/Express/)

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

Starting price

Contact vendor for pricing

Pricing Options

Free Trial

Free Version

User Rating

83%

of reviewers

rated it above 4 stars

[Learn More](https://www.capterra.com/p/29249/Express/)

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

## Features

Features with the highest number of reviews are displayed first. Those that have no reviews appear next, sorted alphabetically.

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

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

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

Transportation Management

3.3 (3)

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

Organize and track the physical movement of goods from one location to another

Accounting

4.0 (2)

50.00% of 2 reviewers that rated this feature as important or highly important

Built-in accounting to manage ledger, accounts payable/receivable, financial reports, etc.

Tailwind TMS 47 features

Outsource and manage third party logistics

Built-in accounting to manage ledger, accounts payable/receivable, financial reports, etc.

Application programming interface that allows for integration with other systems/databases

Create, manage, and send invoices or bills to customers

Find, compare, and select the most time/cost-effective freight carrier

Manage and track all internal and external communication conducted via calls, email, text, or chat

Centralized database of stakeholders and their contact information such as names, address, phone number etc.

Built-in customer relationship management (CRM) capabilities or integration with a third-party CRM system

A collection of customer information such as contact details, demographics, previous interactions, etc.

Store and organize information about customers and previous interactions

A website or login for customers to access information

Import and export data to and from software applications

Manage sending personnel and resources to a site as needed

Track all personnel who operate company vehicles

Manage payroll processing for different driver pay contracts

Transfer of data from one computer system to another

Management of commercial motor vehicles for work-related purposes

Intended to be used by freight brokers and logistics companies

Monitor fuel consumption and optimize fuel usage

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

Information, data and reports that are being tracked over time

Management of inbound and outbound shipments in the context of international trade

Freight forwarder/forwarding agent that transports cargo internationally with knowledge of customs, and international boundaries, etc.

Track driver locations on a map in real time

Set up process for efficient load building, routing, and distribution

Freight forwarder/forwarding agent that transports cargo domestically with specialized knowledge of local logistics services

Trucks that do not reach full load and can be shared

Manage, maintain and track the performance of assets and equipment

Schedule predetermined or ad hoc maintenance services and labor requests

Log miles driven for tax deduction or reimbursement purposes

Access the system via a mobile application

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

Track orders throughout the fulfillment process

Integrates with QuickBooks

Generate quotes or estimates for customers

Track/optimize rates in relation to usage

Notifications that are delivered to users as soon as an event occurs

View and track pertinent metrics to find patterns and gain insights from data

Plan daily routes to optimize employee scheduling and provide directions

Plan availability and assign specific time slots for tasks and resources

The software will assign a tracking number associated to the order number to track the physical progress of the package in delivery.

Set up connections to third-party platforms to improve business processes

Organize and track the physical movement of goods from one location to another

Record of trip details

Track and manage transportation of large cargo that fills an entire trailer/truck

Track and monitor how vehicles are used

Official shipping document that identifies origin and destination of the shipment, weight, freight, and other details of goods

Get Advice

We can help you find the software with the features you need.

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

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

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

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

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/)

Popular comparisons

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

Independent research methodology

Capterra's researchers use a mix of verified reviews, independent research and objective methodologies to bring you selection and ranking information you can trust. While we may earn a referral fee when you visit a provider through our links or speak to an advisor, this has no influence on our research or methodology.

[Learn more](https://www.capterra.com/resources/proprietary-data-research/)

How Capterra verifies reviews

Capterra carefully verified over 2.5 million+ reviews to bring you authentic software experiences from real users. Our human moderators verify that reviewers are real people and that reviews are authentic. They use leading tech to analyze text quality and to detect plagiarism and generative AI.

[Learn more](https://www.capterra.com/resources/how-we-verify-reviews/)

How Capterra ensures transparency

Capterra lists all providers across its website—not just those that pay us—so that users can make informed purchase decisions. Capterra is free for users. Software providers pay us for sponsored profiles to receive web traffic and sales opportunities. Sponsored profiles include a link-out icon that takes users to the provider's website.

[Learn more](https://www.capterra.com/resources/how-we-ensure-transparency/)