# Page 3 | Tailwind TMS Reviews 2026. Verified Reviews, Pros & Cons | Capterra > Page 3 - Is Tailwind TMS the right Transportation Management solution for you? Explore 97 verified user reviews from people in industries like yours to make a confident choice. Source: https://www.capterra.com/p/275384/Tailwind-TMS/reviews --- Tailwind TMS 4.2 (97) [View alternatives](https://www.capterra.com/p/275384/Tailwind-TMS/alternatives/) Provider data verified by our Software Research team, and reviews moderated by our Reviews Verification team. [Learn more](https://www.capterra.com/our-story/) * * * Last updated March 13th, 2026 # Page 3 - Reviews of Tailwind TMS ## Showing most helpful reviews Showing 51-75 of 97 Reviews Sort by: Most Helpful Rating Company Size Reviewer's Role Length of Use Frequency of Use AB Angie B. Owner Transportation/Trucking/Railroad Used the software for: 2+ years ### "Very happy with Tailwind and their customer service " November 18, 2020 5.0 We love the software and the staff if awesome to work with Pros It’s internet based which has made it very easy to go anywhere and still be able to work Cons There is a few extra steps when importing to Quick Books Review Source Response from Envase December 22, 2020 Hi Angie, thanks for your review! Great to hear that you're using the software where-ever you need to be! CI Carmine I. Freight Broker Transportation/Trucking/Railroad Used the software for: 2+ years ### "Tailwind TMS Performs" November 23, 2020 5.0 VERY GOOD experience overall. I won't even look at others for now. Pros Easy to install, easy to use, great customer service. Cons Making changes to dispatches. Has to be done in multiple places. Review Source Response from Envase December 22, 2020 Hi Carmine, thanks for the review and feedback, we hope you continue to have a good experience with the software! JG Jane G. President Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Love this Software" November 17, 2020 5.0 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! 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. Reason for choosing Tailwind TMS Tailwind seemed to be the one that would most meet our needs. Switched from [TMS.AI](https://www.capterra.com/p/153047/Rose-Rocket/) 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 Review Source Response from Envase December 22, 2020 Hi Jane, we appreciate your review! MB Morgan B. logistics coordinator Transportation/Trucking/Railroad Used the software for: 1-2 years ### "good" January 4, 2022 4.0 Pros dispatch. customer and carrier records. Cons Many times makes me log in every time I click on a new page. Review Source AS Aaron S. GM Transportation/Trucking/Railroad Used the software for: 1-2 years ### "Rouge River Trans Aaron" November 23, 2020 3.0 Its not horrible but i wouldn't recommend Pros software can use from any computer pretty inexpensive no upfront fee Cons to many steps to do simple task ( copy orders) wont let you set a new pickup number or customer order number from copy screen) runs very slow for no reason Review Source Response from Envase December 22, 2020 Hi Aaronwe're continuously updating the software to ensure it speeds up user workflows so appreciate your feedback! JT JOHN T. VP Transportation/Trucking/Railroad Used the software for: 2+ years ### "Excellent TMS" June 23, 2016 5.0 Tailwinds is very user friendly and has customizable features that can be done at the user level or through their support network. Run into an issue? Just call or email their support team, responses are always quick and solutions just as good. Pros We are continuously utilizing more and more of the components of the software every day. TW can be as small or as large a part of your TMS system as you want it to be. Review Source DL Daniel L. Director of Operations Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Robust trucking software that is pleasant to look at with great customer support" April 6, 2018 4.0 Aesthetics was a huge consideration, and who ever designed this software had feng shui in mind, great to look at! Pros You will appreciate the customer support you receive with this software. Tailwind is easy enough to use and very pleasant to look at (which is important if you have to stare at this software for several hours a day). However, the true strength of this offering comes from the company's dedication to making sure that you understand how to use the software and get the most out of it. They have great training videos, and you can set up a personal training session. Everyone I have talked to there is super pleasant and eager to help. Other software companies just hand it to you and say, figure it out and let us know if you need anything. Not Tailwind. They generally want to make sure that the software is a good fit for you and will do back flips to make sure you get what you need. The tip about using multiple browser tabs with different pages of the software open to quickly move between sections, while obvious once you use it, was a great idea I didn't initially think of. Cons It's a bit expensive for a smaller company, but as you grow, they can be flexible with adding features/users for a discount. Review Source MB Mario B. Operations Manager Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Good Product, but too expensive" July 5, 2022 3.0 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 AZ Al Z. General Manager Transportation/Trucking/Railroad Used the software for: 1-2 years ### "Great Software" November 30, 2020 5.0 Very good software Pros Ease of use and that we can access from anywhere - web based Cons Processing deposits - When crediting short pays or over payments. Review Source Response from Envase December 22, 2020 Hi Al, thanks for taking the time to leave us a review and feedback! LB Lovepreet B. Director Transportation/Trucking/Railroad Used the software for: 6-12 months ### "Review" November 17, 2020 5.0 Pros I like how easy it is to use the software, easy to navigate. Cons Sometimes the software is really slow and I have to reload a lot Review Source Response from Envase December 22, 2020 Hi Lovepreet, thanks for your review and the feedback! We are sorry to hear you are having to reload the software at times. We are always updating our software to provide the best experience for our customers. Your issues have been brought to the attention of the development team to ensure adjustments will be made. HJ Harmun J. Dispatch Transportation/Trucking/Railroad Used the software for: 6-12 months ### "Dispatcher Tailwinds" December 28, 2021 4.0 Pros I really like the POD app. Drivers dont have to send emails or let us know when they check in or check out. The app takes care of all of that. Keeps our customers informed as well which is great Cons Can't add extra stops without adding additional shipments Review Source LN Laura N. ACCOUNTING ASSISTANT Transportation/Trucking/Railroad Used the software for: 6-12 months ### "choose TW" December 21, 2021 5.0 Nice experience so far Pros eASY TO LEARN AND USE. TRANING VIDEO VERY HELPFUL. GOOD CUSTOMER CARE Cons Nothing, I think it work well for our industry Review Source ST Simon T. General Manager / Owner Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "User friendly and highly functional hosted TMS" December 6, 2018 5.0 I was up and poking around the system within a day. Tailwinds set me up with live training webinars which gave me a good tour of the system functionality. There are more (free) in-depth webinars available which I haven’t taken yet, but the system is so intuitive and easy to use that I haven't felt the need to. Data is easy to export to work in spreadsheets. Forms are all there like invoices, bol, etc... Tech support is very responsive and easy with the the online chat and phone. Pros I was able to setup my new Freight brokerage business and be up and running with my first loads within a week of getting setup on Tailwinds. Cons I wish is was more customizable. Specifically the email forms from the system. Being able to customize email subject lines with data variables, etc.. Review Source DP Dannielle P. Owner Transportation/Trucking/Railroad Used the software for: 6-12 months ### "Small Business Solution" November 30, 2020 4.0 Pros Dispatching side of things, ease of use when dispatching drivers Cons Accounting side is not a diversified as I would like Review Source Response from Envase December 22, 2020 Hi Dannielle, we appreciate your feedback and review! SR Sarah R. Dispatcher Used the software for: ### "Overall, I would recommend this program to any dispatch in the industry. " May 6, 2009 4.0 Overall, I would recommend this program to any dispatch in the industry. It is a very user friendly system that provides all the necessary information to complete the required daily processes. Pros Tailwinds provides a clear board that uses a variety of colours and headings to make it easy to read and offers a great deal of information. The setup of the program is straightforward, allowing for smooth work processes. The error popups provide a clear explanation of the problem so you know where and how to correct the error. They also have excellent customer support services with representatives who are able to explain things in a manner that is easy to understand. Overall, it is very user friendly. Cons The warnings can cause an inconvienence when they continuously popup everytime something is resaved. In addition, refreshing the screen can take a great deal of time in the receivables section. Review Source KA Kevin A. Vice President Used the software for: ### "Tailwind " March 9, 2016 5.0 "There is no other way to go than being on a maintenance and support plan with Tailwind. I have noticed a huge improvement with the new Customer Success Platform that is being offered. Previously, we were not using the system to its full potential. Angelena reached out to us this year and ensured that we are receiving the attention we require. Specifically, as a Platinum customer I will receive a one on one session with the "awesome" Lynda Clare. I am confident that as a result of this intervention we will receive all the help we need to learn how to use the system comprehensively and to run reports that will further align my business needs with the Tailwind Software. If we have a technical problem your support team helps us immediately and our issues are resolved. I have enjoyed the stability of your support team; Mark, Sandy, Eg and Richard are all great at their jobs and walk us through to the answers we require. Working with Tailwind in 2016 will enable me to get my business to the next level of success." Review Source sK steve K. Government freight manager Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Great Software Very User Friendly" January 31, 2017 5.0 Just got off the phone with rep and I wanted let everyone at Tailwind know how impressed we are with your system. This is the most user friendly and customizable software we have looked at. You are headed in the right direction because not everyone does it the same and you have created your software with that understanding in mind. Thanks for all the hard work and listening to our ideas and being able to make those ideas work. Pros They have simplified the settings to the point you can customize it to fit your business whether its asset based or brokerage or owner operators Cons I have not found anything i dont like they have addressed all our concerns and adjusted their software to fit us Review Source NS Natalia S. Translator & Logistics Developer Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "The culture of Tailwind is quality and everyone is very knowledgeable, helpful and kind." August 10, 2017 5.0 All I need to make our business going : Database, Accounting & Administration, Equipment and Driver Management, Quotes and Orders, Alerts and Load Tracking & Reporting. Among many other operations. Thank you, Tailwind! Pros The fact that Tailwind is an "all in one application" helps us run the business more effectively and we have access to it from any device. The features are unique and the platform is constantly improving to fulfill every need. Cons I have a hard time coming up with something because if I do have an issue that needs to be resolved right away, I immediately have a solution from Tailwind's support system. Review Source GH Gretchen H. Account Manger Used the software for: ### "Very pleases with the classes and satified with Tailwind " June 9, 2016 5.0 The training classes were informative and Lynda thoroughly answered all of my questions. I am very new to the transportation industry - Lynda took the time to explain the terminology to me so I have a better understanding of the industry in general and my business specifically. The program is fairly easy to understand once you go to training and if you access Lynda to have a private session. The program absolutely saves me time by helping me to get organized with my tasks. I deal with the accounting side of the business and because Tailwind has a colour coding system in place, I am able to see what invoices are due ahead of time. I will be able to get my invoices in and out ON TIME. My staff in the Dispatch side of the business tell me that Tailwind has really helped them to do their jobs well. Lynda, has a very nice demeanour and voice so she is not only knowledgeable but also very easy to listen to. Gretchen Hayes, Reliable Source Logistics Account Manager Review Source NC Nick C. Vice President Logistics and Supply Chain Used the software for: Less than 6 months ### "tailwind" January 4, 2022 4.0 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 RL Roxanne L. H/R Accounts Payable Clerk Used the software for: ### "We made the transition from a custom DOS program to Tailwind last year 2015" February 3, 2016 5.0 Our old system was DOS based and when we upgraded our computers we needed to get a new Transportation Management System. After a year of using Tailwind, I feel like I understand how to use the system, I can get help when I have a problem and I have the ability to cross-train with my staff so the system is continually adapting to our evolving business needs. In just 1 year Tailwind Support has grown and it shows. As a Platinum customer, when I call in with a technical issue, your support team answers the phone promptly and logs into my system to help me. They can see my screen, I love learning and your support team helps teach me how to tackle my software issues. Customer service is better than ever. I would recommend to all of your customers to choose a Platinum level Maintenance and Support Plan. Review Source AS Amardeep S. President Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Great software for start up trucking companies" November 24, 2020 5.0 Pros You can really save a tonne of time and effort by using Tailwind to it's full advantage. Easy to use and great to stay organized Cons It can be a bit slow and glitchy at times Review Source Response from Envase December 22, 2020 Hi Amardeep, thanks for your review! GO Gilberto O. Key Account Manager Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "A little complex to learn" January 22, 2019 5.0 It is a good software to coordinate the freights once you learn how to use it. Pros That you can link it with your QuickBooks account. Cons It is very difficult to learn. It took me over a month to have a full understanding of it. Review Source Response from Envase January 23, 2019 Thanks Gilberto, Regarding your comments on software complexity - please don't hesitate to reach out to us using the in-app chat with support for help as you need it. You can also attend our free LIVE training sessions that happen twice a week! DF Donna F. Dispatch Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Feedback" November 30, 2020 4.0 Pros Web base, the support team, the flow of the system Cons quotes - we should be able to add multi rates (ie 1, 2,3 skids...etc) would be nice to sort by carrier equipment Review Source Response from Envase December 22, 2020 Hi Donna, we appreciate your feedback! JN Jag N. Owner Used the software for: ### "excellent. always there when we need them." November 20, 2015 5.0 Jag Nahal Owner of Manney Transport: Tailwind is a huge part of running our business and a necessary tool for all companies who handle varying types of loads. We specialize in local, flat bed, intermodal, and long haul loads, they are all different. Tailwind is easy to customize making it efficient for us to track our loads including the multiple picks and drops we need to follow. I know that dry van and reefer load tracking is just as strong within Tailwind. We also are able to track and complete all our accounting functions, which is invaluable and necessary for any company. I've never had a complaint with the ability, and availability to receive support when learning a new feature or adding to the vast capabilities of Tailwind. Review Source Similar Products Featured