Tailwind TMS 2026: Benefits, Features & Pricing

Software Advice offers objective insights based on verified user reviews and independent product and market research. When our advisors match you to a software provider, we may earn a referral fee.

How Software Advice ensures transparency

Software Advice lists all providers across its website—not just those that pay us—so that users can make informed purchase decisions. Users can talk to our advisors for free to receive software recommendations matching their needs. Software providers pay us for sponsored profiles to reach users interested in their products.

How Software Advice verifies reviews

Software Advice carefully verified over 2 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.

Independent research methodology

Researchers at Software Advice 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 talk to an advisor, this has no influence on our research or methodology.

Wondering if Tailwind TMS is right for your organization?

Our Transportation Management Software selection experts can help you in 15 minutes or less.

On this page

Overview
Pricing and Plans
Features
Integrations
User Reviews

Overview

Tailwind TMS

4.3

(97)

Pricing

Starting at $99.00 per month

About Tailwind TMS

Tailwind Transportation Software offers a cloud-based transportation management solution built for small to mid-size trucking companies and freight brokerages. Tailwind features a customer and vendor database, quoting and order modules, a dispatch system and more.

Tailwind’s customer and vendor database allows users to track and maintain contact information. Users can manage quotes, work orders and accounts receivable, view customer rate histories and track equipment maintenance, claims, incidents and accidents. Tailwind also features a dispatch and shipment tracking system, route management and user alerts.

Tailwind features a sales commission system, preconfigured admin, accounting and operations reports and a data import tool, as well as QuickBooks sync. The system also offers load board integrations and a dedicated mobile app. Driver and carrier settlements, GPS integration and a customer portal are also available.

Phone, email and in-app chat support are available. Pricing is per user per month with no contracts necessary.

Tailwind TMS Screenshots

Tailwind TMS Pricing and Plans

Starting price: $99.00 per month

Free Trial

Free Version

Pro

$99.00

per user, per month

Plan 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

Enterprise

$149.00

per user, per month

Plan 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

Plan 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

Confused about pricing? We've got you covered.

Get a personalized pricing breakdown tailored to your specific needs—no guesswork, no generic estimates.

Tailwind TMS Features

Popular features found in Transportation Management
Billing & Invoicing
Customer Management
Dispatch Management
Fleet Management
Live Driver Tracking
Order Management
Real-Time Monitoring
Routing
Scheduling
Shipping Management
More features of Tailwind TMS
3PL Management
Accounting
API
Carrier Management
Communication Management
Contact Database
CRM
Customer Database
Customer Portal
Data Import/Export
Driver Management
Driver Settlements
EDI
For Freight Operations
Fuel Management
GPS
Historical Reporting
Import/Export Management
International Forwarders
Load Optimization
Local Forwarders
LTL/Shared Truckload
Maintenance Management
Maintenance Scheduling
Mileage Tracking
Mobile App
Order Tracking
QuickBooks Integration
Quotes/Estimates
Rate Management
Real-Time Notifications
Reporting/Analytics
Route Management
Shipment Tracking
Third-Party Integrations
Transportation Management
Trip Logs
Truckload Management
Vehicle Management
Waybills

Tailwind TMS Integrations

Google Maps

QuickBooks Online Advanced

EZTrack

Descartes MacroPoint

EZCheck-In

Samsara

Tailwind TMS User Reviews

Overall Rating

4.3

Ratings Breakdown

53%

32%

10%

Secondary Ratings

Ease of Use

4.2

Value for money

4.3

Customer support

4.6

Functionality

4.0

Francois D.

Verified reviewer

Logistics and Supply Chain

2-10 employees

Used daily for more than 2 years

Review source

Reviewed August 2025

Do not recommend

Previously 5

Ratings Breakdown

Ease of use

Previously 5

Value for money

Previously 5

Customer support

Previously 5

Functionality

Previously 5

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.

Frank L.

Verified reviewer

Automotive

51-200 employees

Used daily for less than 12 months

Review source

Reviewed December 2020

Transportation Software for an Auto Auction

Overall, I researched numerous Transportation Apps and this one had the best features for our industry. It seems more suited to brokers than an auto auction but it works well. The customer service has been exceptional. The price point is a little high considering the lack of GPS and driver's app functionality.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

What I liked most about the software is that it is very versatile. It tracks everything for us from pickups and deliveries. For the first time, we are able to quantify the value of transportation in a market of ever-changing agreements and pricing.

Cons:

What I like the least from the software is that the drivers App doesn't show enough information for the pickups and deliveries. Also, there is no GPS integration for the drivers. With other Apps, drivers can just press the address and it automatically sends them to Google maps or Waze. Additionally, there should be an integrated GPS for truck routes to avoid non-commercial routes, low bridges, and tight intersections.

Reasons for choosing Tailwind TMS

Tailwind was the most comprehensive App on the market that I researched. I did over a dozen webinars with different companies and I finally settled on Tailwind. It's not perfect, but it has a lot of advantages for our company and industry.

Reasons for switching to Tailwind TMS

The towbook app was great except that we couldn't clearly distinguish from pickups and deliveries. It was only $200 a month. Sometimes the App would crash holding our work hostage for an entire day.

Vendor Response

Hi Frank, Thanks for your review and the feedback! We will update our development team with your suggestions to see what changes may need to be made. Our integration with EZ-Track also provides you with free load tracking--25-loads tracked in our Pro tier, 50 in Enterprise, and unlimited tracking in our Unlimited tier!

Replied December 2020

Martin - John S.

Verified reviewer

Logistics and Supply Chain

11-50 employees

Used daily for less than 12 months

Review source

Reviewed December 2024

Operation Manger and lead dispatch

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

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

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.

Peter K.

Verified reviewer

Transportation/ Trucking/ Railroad

11-50 employees

Used daily for more than 2 years

Review source

Reviewed November 2020

Using Tailwind

Great experience. Easy to use and support is at your fingertips with high quality videos tutorials. technical support is very responsive should you require assistance.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

Web based interface with proven stability is a key factor to the Tailwind Product. It does everything you need in terms of a transportation management system.

Cons:

No ability to tap into the database and create custom reporting on your own without creating an expensive API.

Reasons for switching to Tailwind TMS

Gain the ability to track our loads and as well as our drivers. The POD features are important as well.

Vendor Response

Hi Peter, thank you for the review. Our new Unlimited tier that we launched in September includes API web-hooks which might help.

Replied December 2020

Jane G.

Verified reviewer

Transportation/ Trucking/ Railroad

11-50 employees

Used daily for less than 6 months

Review source

Reviewed November 2020

Love this Software

We switched our TMS system and had so many problems. Finally, after 4 months we switched to Tailwind...and we have never looked back. It's been nothing but a positive experience! The bottom line is they overpromised and underperformed!

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

User friendly. It is very easy to use. And when I can't figure something out, support is right there to help me! It is also affordable!

Cons:

Honestly, there is nothing about Tailwind I don't like.

Reasons for choosing Tailwind TMS

Tailwind seemed to be the one that would most meet our needs.

Reasons for switching to Tailwind TMS

There are too many problems to list them all. Invoices were never received by customers; paying settlements and payroll was complicated and difficult to be sure of accuracy, and so much more

Vendor Response

Hi Jane, we appreciate your review!

Replied December 2020

Richard A.

Verified reviewer

Transportation/ Trucking/ Railroad

51-200 employees

Used daily for more than 2 years

Review source

Reviewed December 2020

Product quality

For our current size, it has checked the most important boxes. Critical Dispatch, billing, AR mgmt functions are covered for the most part. If we continue our growth we will have to migrate to a different platform without some developments on Tailwinds side. For reference, our we are a 45 truck fleet.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

Easy to navigate. Web based platform. Reasonably committed to product improvement and feedback from end users.

Cons:

Lacking integrations with outside vendors (specifically ELD platforms, EDI platforms, Load boards and tracking softwares). POD complete app is functional, but has issues with format and size of file when transferring to customers for invoicing. Seems like they could partner with a transflo or some other software that already has the software built to strengthen their offering. No admin app for viewing platform on tablet/phones. Reporting could use some adhoc capabilities.

Reasons for choosing Tailwind TMS

Price, ease of use, ease of transition.

Reasons for switching to Tailwind TMS

Previous platform was outdated, did not offer sufficient AR tracking capabilities, no ability to capture and transmit BOLs/PODs.

Vendor Response

Hi Richard, Thanks for your review and the feedback! Our recent partnerships with Kleinschmidt (EDI), EZ-Track and Trucker Tools (tracking) should help address some of your integration needs, and there's also an upcoming integration with Samsara (ELD) that will be announced officially soon! And there are more integrations slated for 2021 :-)

Replied December 2020

Katherine B.

Verified reviewer

Transportation/ Trucking/ Railroad

2-10 employees

Used daily for less than 6 months

Review source

Reviewed November 2020

NOT happy with support!

i am not happy with it. I think it is super expensive for the service we are getting!

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

At the beginning I liked the ease of use and the customer service however over the past month, I have been VERY unhappy with the software. *Customer support is AWFUL! I tried to get them to call me over a serious issue and they wouldn't call me back and then another time i had to wait an hour *Issues with printing cheques, this is wasting alot of my time, it is taking me 10 times longer than it did with my previous system

Cons:

the "accounting side" of the system, it doesn't work at ALL! customer service

Reasons for switching to Tailwind TMS

Thought your system had more functions and easier to use but it turns out it does in some areas but others, it's AWFUL!

Vendor Response

Hi Katherine, I'm disappointed to hear about the apparent poor service you report to have received from Tailwind. We do really pride ourselves on providing prompt and full support - which is why we keep it in-house rather than offshoring. I have reviewed the latest set of conversations you have had with the Tailwind Support team, and it appears that a solution for your issues has been found (and thank you for the latest 'Amazing' conversation rating you provided!). That said - our goal at Tailwind is to provide you with a transportation management system that will allow you grow your business - and ideally, give you a bit more time at the end of your day) - so if you do require additional support - please do reach out (support@tailwindtms.com; 1-866-441-0441).

Replied December 2020

Djuro K.

Verified reviewer

Transportation/ Trucking/ Railroad

11-50 employees

Used daily for free trial

Review source

Reviewed January 2021

Tailwind TMS is the best you will find and love !!!!

Great software, but just that driver app needs work.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

There is lots of pros here, its online based, and you should be looking at online based, no server or up front cost, and you can use it from anywhere. Software has all the things you can think of. Great reports, and you can store files on trucks, drivers, and all your exp data. You can dispach the load, customize the payables the way you want, There is ways to add deductions and fuel can be imported, for owner operstor deductions, and software will pay the truck not the driver as this is important for owner operators, and if they have there own drivers this ia probably 1 of 15 tested products that has this option. You can easly export documenta as 1 file for your factoring. There is many many grest things. POD Complete is free.... Other simular solutions charge 7-25,000$ Down payment and 800-1300 a month. Plus 10-20$ for a driver app.

Cons:

Now, yes there is cons, One is sometimes its slogish and it takes a bit to load but not that bad. The other one, POD Complete , well its a little incomplete, it has the options you need, you send the laod and driver can arrive depart, great, attach POD its there but, it needs work, this needs to have transflo options or something like a camsxanner, just to let you cut the page adjust it before you send it over. Plus it would take lot less storage if it was a scan doxument, this way its a picture, not that great for billing, it does work. But I think tailwind shoudl stop all other areas of development cuz they are great and spend some time here, make this app a killer. Evan charge 10$-20$ a driver /mo I would pay it just to get a better app. It needs to have scan features, we all need to get those Bols in good quality, and we dont want to have to use translfo or camscaner or other apps and than have to import the documents into tailwind.

Jason D.

Verified reviewer

Transportation/ Trucking/ Railroad

2-10 employees

Used daily for more than 2 years

Review source

Reviewed November 2020

Best TMS Software

This software allows us to keep track of shipments, send out rate confirmations and even invoice customers all through the same easy to use application.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

This software is so easy to use and intuitive. It can be used anywhere and has the features that other softwares charge 10+x the amount for.

Cons:

Each new device you use the software on, you have to reset the setting, but not something that happens very often. Minimal cons to this software.

Vendor Response

Hi Jason, thanks for the great review!

Replied December 2020

Daniel T.

Verified reviewer

Import and Export

11-50 employees

Used daily for less than 12 months

Review source

Reviewed January 2019

Tailwind Review

great TMS , it can handle my loads very easy, is the only software that I know , than can handle an international load, taking a mexican carrier, with their own trailer number, involve a wharehouse , transload the product to a US carrier with a different trailer number , and give you the avaibility to track the load in one single order, not just that, it also provide indivual instructions and BL for each party, and receive the invoice for each carry involve so payments for each of them can be done with the proper administration, and for you customer can get togther all this job and send them just one invoice for the all service... this TMS is great

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

Is very flexible and you are able to creat the orders as you want

Cons:

Traying to get automatic commsion payments for your personel can be tricky but once you get it done works great

Vendor Response

Thanks Daniel - we appreciate the feedback!

Replied January 2019