# Page 4 | Tailwind TMS Reviews 2026. Verified Reviews, Pros & Cons | Capterra > Page 4 - 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 4 - Reviews of Tailwind TMS ## Showing most helpful reviews Showing 76-97 of 97 Reviews Sort by: Most Helpful Rating Company Size Reviewer's Role Length of Use Frequency of Use ME Mitchie E. Used the software for: ### "Useful, easy-to-use software and excellent customer support" May 25, 2016 4.0 The software is good for tracking shipments and for the visibility it provides for all of our employees. Anyone in the office can pull up the orders and dispatches and know exactly what is happening. We phone in to the support department to ask for help with invoicing and generating reports. I appreciate that they get back to us promptly, within the same business day, and that they have a great way to connect with us on an interpersonal level. The software is easy to learn and we know who to call to get our questions answered. The support department is great at explaining the system to us in plain language that we can understand. As our business grows we continue to learn about how the system can help us further. Review Source DN Dana N. Assistant Office Manager Used the software for: ### "I would recommend this system to any company that had a large enough fleet. " May 6, 2009 5.0 I would recommend this system to any company that had a large enough fleet. Pros This system is great for trucking businesses. It is fairly easy to learn and has lots to offer. I have yet to stop learning new things from this system. The Driver Pay Wizard is very handy for my department. I am able to immediatley determine if PRO#s have or have not been paid to a driver. My old method was to look through every check they have received from us! Cons I sometimes receive some errors that are just randomn. Customer support is always there to help! Thank you Kenny and Kyle... Review Source CC Chris C. Teacher Used the software for: ### "Teaching Tailwind" October 1, 2010 5.0 Use it, you won't be disapointed Pros Love the program. As a teacher at McBride instructing Dispatch training, I find the Tailwind program perfect. Even students with minimal computer skills find the program easy to use. As I don't have 20 years worth of computer skill, I was unsure as to how quickly and how well I could learn the program. Rest assured, if you can turn on a computer, then you can do tailwind. I would recomend(and I have) the Tailwind program for anyone looking for a good dispatch software program. Cons no complaints Review Source BW Brandi W. manager Logistics and Supply Chain Used the software for: 2+ years ### "Tailwind review" November 30, 2020 4.0 Pros The ability to customize the software and make changes Cons The long turn around time on errors or fixing bugs/problems Review Source Response from Envase December 22, 2020 Hi Brandi, thanks for the review and feedback, we appreciate it! PR PARM R. OPPERATIONS Used the software for: ### "opp Manager" September 30, 2010 5.0 I WOULD FULLY RECOMMEND TRUCKING COMPANYS TO USE THIS Pros I WOULD SAY IT IS A REALLY GOOD SOFTWARE WHICH MEETS YOUR NEEDS , BUT IT WILL TAKE SOME TIME FOR YOU TO GET USE TO IT. AND ONCE YOU DO YOU WILL BE ABLE TO MAKE YOUR DISPATCH ALOT EASIER.I HAVE USED SOME OTHER ONES THEY ARE PRICEE , SO THE BEST THING ABOUT THIS ONE IS YOU CAN PAY IT ONCE AND MONTHLY COST IS VERY LOW. MOST OF THE SOFTWARES YOU ARE PAYING ANYWHERE FROM 150 TO 200 $ WITH THIS ONE YOU CAN GET AWAY WITH ABOUT $50 Cons THERE IS NOT MUCH I CAN SAY Review Source RB Robert B. VP Finance Used the software for: ### "Great support" December 18, 2014 5.0 Pros: - Support team is quick to respond to requests and provide solutions. - Software is easy to use and understand. - Customizable to match our specific business needs. Cons: - User interface could use a refresh. We have been using Tailwind for over 10 years and it has been a big part of our growth. We have recently reviewed the marketplace to ensure we were still being well looked after. After this review it was clear that Tailwind was the best at managing our specific business needs. Including the ability to manage bulk commodity billing, fuel invoice importing, satellite dispatch integration, and freight brokerage. Review Source JP Jamie P. Owner Used the software for: ### "Our customers are happier since we installed the software. Their invoices are much more detailed." May 6, 2009 4.0 Our customers are happier since we installed the software. Their invoices are much more detailed. We can quickly and accurately track loads and never lose orders which has saved us and the customers time and money. Pros Orders will never be lost. If an order is not delivered it cannot be billed. Even if the paperwork is misplaced and the order delivered, we will still have the order in the system to bill. The ability to sync to our accounting makes our accountants job easier. Cons None that I can see. Review Source JG Jim G. Customer Service Manager Used the software for: ### "9.5 on a 10.0 scale" May 7, 2009 4.0 9.5 on a 10.0 scale Pros has centralized all of our info into one database, with up-to-date tracking information at all times. We With three locations stretching from coast to coast, our database is centralized. All tracking information is now "real time" and accessible at all times. We would recommend Tailwind software without hesitation!" Cons Cost of additional users is high Review Source TC Tyesha C. Used the software for: ### "the software is excellent and very detailed; it takes some getting used to, but it is thorough!" September 23, 2015 5.0 About two months ago I temporarily suspended my subscription with Tailwind because I was not fully ready to start my new brokering business. This week I decided to return to tailwind because I remembered how professional and caring the Tailwind team was (specifically, Lynda Clare, Implementation/ Training Manager and Angelena Helten, Client Success Manager). Tailwind left a long-lasting impression that will resonate with me as nothing more than "A1, first-class service!" Review Source HS Handeep S. Administrative Manager Used the software for: ### "Easy and efficient" May 13, 2016 5.0 Tailwind has made our daily routine much easier and efficient. Tracking equipment, payables and receivables, as well as, sending orders and quotes is quite simple. Tailwind's support department is good, anytime we have a problem we are able to get answers promptly. I did a little bit of training with Tailwind's trainer, but I mostly learned how to use the system by navigating through it on my own. I found it easy to use, it made sense to me. Review Source GD Greg D. Vice President Sales & Operations Used the software for: ### "I have used the software since its inception and experience all the updates" May 26, 2016 3.0 The software is easy to understand and provides all TMS functions from dispatch, AP, AR, to account management reporting. It has some nice features due to its integration with mileage programs, posting sites, and reporting. CMS supports multiple users and most importantly works using multiple currencies for CDN and USD. Some sections need improvement because of extra page clicks, but I am told this will be addressed soon. Review Source RT Ron T. Controller Used the software for: ### "The system is very user friendly." May 6, 2009 5.0 The system is very user friendly. It's so easy to enter new orders, make corrections, research and do invoicing. We also like how easy it is to look up the company financial sales, cost and receivables by using the report function that is available. We highly recommend Tailwind; it's been a number one tool for us.' Pros easy to use Cons none that comes to mind Review Source LP Lynda P. Controller Used the software for: ### "We are in awe that our dispatching and invoicing can be so streamlined and easy." May 6, 2009 4.0 We are in awe that our dispatching and invoicing can be so streamlined and easy and wondering why we didn't take this step long ago. Pros Ease of use Eliminates paper Security settings for personnel Management Reports Cons Didn't understand just how great the program was thru the sales process until we started using it Review Source DS Don S. President Used the software for: ### "The system is a very good value , customer service is excellent. " May 7, 2009 4.0 The system is a very good value , customer service is excellent. Pros Very user friendly, the ability to use templates makes order entry fast & easy. Integrates very well with Quick-Books Cons Would like to see a driver/ tractor planning feature to pre-plan trips. Review Source BM Balihar M. Operations Manager Used the software for: ### "Excellent program for Transportation. " May 10, 2009 4.0 Excellent program for Transportation. Pros Very user friendly, very simple and easy to find information. I can get information from 3-4 years from using the system about driver, power units, trailers, customers, vendors etc. Cons Load Planning could be a little better. Review Source RR RANDY R. OPERATIONS Used the software for: ### "12345" March 6, 2012 3.0 Program works great when it works. Pros Been with Tailwinds since the start. Gave them alot of ideas to update and make changes. always good to work with. Cons Trying to get a straight anwser on features that have to be fixed. Review Source AO Allen O. President Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Big Sky Dispatch" November 30, 2020 5.0 Pros How easy it is to use. and great support Cons you can't add items to ship list at all. Review Source Response from Envase December 22, 2020 Hi Allen, thanks for your great review and feedback! We are really proud of our 'on'-shore support team! RV Ryan V. President Used the software for: ### "Great!" May 13, 2016 5.0 I have had a great experience with the software there are a lot of functions included that I do not utilize however should I choose to the staff is very responsive and would gladly be able to train me on anything I needed to know. Review Source YH Yvonne H. Controller Used the software for: ### "It's good value for the money spent and I would recommend it to others." May 6, 2009 4.0 It's good value for the money spent and I would recommend it to others. Pros Order entry and dispatching are easily handled with CMS Cons Having to use a separate accounting software for financials Review Source LB Lea B. Dispatch Manager Used the software for: ### "Excellent" October 9, 2015 5.0 Tailwind has given us greater visibility into our dispatch and invoicing, as well as our daily operational challenges. It is extremely rewarding to work with a company that has such exceptional customer service! Review Source TO Tom O. Finance Specialist Used the software for: ### "A Complete Trucking Software Package" October 5, 2015 4.0 Pros: Ease of use, simplistic tracking, comprehensive billing. Tech support is very responsive Cons: Some quirks when synching to Quickbooks Review Source TA Travis A. General Manager Used the software for: ### "Great Product, easy to learn" May 16, 2016 5.0 Tailwind is easy to use, and very compatible with our needs. The support staff is helpful. We have had great business success with Tailwind Review Source Similar Products Featured