# Tailwind TMS Reviews 2026. Verified Reviews, Pros & Cons | Capterra > 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 # Reviews of Tailwind TMS Ease of use 4.2 Customer Service 4.5 ## Pros and Cons in Reviews Jason D PresidentTransportation/Trucking/Railroad, 2 - 10 employeesUsed the software for: More than 2 years. “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.“ November 23, 2020 MS Martin - John S Operation - Dispatch LeadLogistics and Supply Chain, 11 - 50 employeesUsed the software for: 6-12 months. “Originally hey this is pretty good but since there so called update or new platform its gone to crap.“ December 11, 2024 MB Mario B Operations ManagerTransportation/Trucking/Railroad, 2 - 10 employeesUsed the software for: Less than 6 months. “Their CS team is decent.“ July 5, 2022 MS Martin - John S Operation - Dispatch LeadLogistics and Supply Chain, 11 - 50 employeesUsed the software for: 6-12 months. “Getting service is terrible def wouldn't recommend it to anyone anymore“ December 11, 2024 AK Ashveen K DispatcherTransportation/Trucking/Railroad, 11 - 50 employeesUsed the software for: Less than 6 months. “Very satisfactory and easy to navigate around“ August 29, 2022 Francois D PresidentLogistics and Supply Chain, 2 - 10 employeesUsed the software for: More than 2 years. “When working of the order list or dispatch list, when you get out of the order or dispatch, you lose all the filters applied.“ August 28, 2025 AD Audrey D ManagerTransportation/Trucking/Railroad, 501 - 1,000 employeesUsed the software for: More than 2 years. “Anyone I train seems to manage navigating it with ease.“ January 4, 2022 PC Patty C AccountingSpecialistTransportation/Trucking/Railroad, 11 - 50 employeesUsed the software for: More than 2 years. “I have to size ALL my paperwork because of the transmissions fail on most every single one that has to be sent to customer.“ January 4, 2022 ## Showing most helpful reviews Showing 1-25 of 97 Reviews Sort by: Most Helpful Rating Company Size Reviewer's Role Length of Use Frequency of Use AM Altaf M. Vice President Transportation/Trucking/Railroad Used the software for: 1-2 years ### "Powerful Tool for Small to Medium Trucking Operations." November 17, 2020 3.0 Tailwind is a must have for any trucking company, big or small. Using tailwind has really cut down the amount of time spent each month on administrative tasks. We are looking forward to growing with Tailwind and are excited to see the software evolve. Pros The biggest pro for tailwind is its customer service and development team who take your feedback very seriously and are always ready to help you out The software changes every day and if there is a feature or functionality that may not be available, a simple suggestion of yours might just be in the next update. Another pro of the tailwind software is the pricing. When compared to other TMS's, the tailwind system offers the same features of the enterprise and large suite transport systems bundled in an affordable system that you can really customize to fit your needs, and there is no initial setup cost like many other programs. Tailwind also offers free webinars every week for you to either brush up on the software or train a new employee which is very convenient. The system is online based so you are able to access it anywhere and at any time and does not require you to set up a server in your office like many others. One of our favorite features of this software are all the integration, the tailwind team has partnered up with the best service providers (Truckertools, Border Connect,RMIS etc), in the transportation industry to provide an immersed experience when using the software. Cons There are not many cons to Tailwind but being an online-based system comes with its negatives as well, and the biggest downfall of the system is that it can be very sluggish at times taking a few seconds to load between screens, and does not fully load the page at times. The software also lacks the ability of end-user customization of documents and the interface. Another con is that the software is mostly designed as a full truckload system and lacks in features for the consolidation of LTL. The accounting portion could use some work as well. Alternatives considered [TMS.AI](https://www.capterra.com/p/153047/Rose-Rocket/)[AscendTMS](https://www.capterra.com/p/122488/AscendTMS-Logistics-Software/)[ITS Dispatch](https://www.capterra.com/p/106760/ITS-Dispatch/)[Avaal Express](https://www.capterra.com/p/111633/Avaal-Express/) Review Source Response from Envase December 22, 2020 Hi Altaf, thanks for the great review! We're glad to hear that Tailwind has helped you reduce the time spent on administrative tasks so you can focus on growing your business! AD Audrey D. Manager Transportation/Trucking/Railroad Used the software for: 2+ years ### "Worthy of managing your transportation needs" January 4, 2022 5.0 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. Reason for choosing Tailwind TMS We liked the product and the pricing was mid range. Review Source Response from Envase 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! MM Michelle M. Operations Manager Transportation/Trucking/Railroad Used the software for: 2+ years ### "Operations Manager" December 23, 2021 4.0 Pros Fairly easy to use. Relatively straight forward. Cons Poor transaction history and being able to see who did what in the system. Have to go to help desk for that. Not necessarily the right fit for a heavy haul operation, more suited towards brokering and more basic legal and OD loads. On that side it is fantastic. Cannot copy anything but orders - would be nice to copy quotes as well. Definite reporting limitations as well. Help lookup on specific topics is limited and not as detailed as it should be. Have to rely on helpdesk to answer some questions and it is frustrating to not be able to speak to a person and have to do it all through chat. Review Source TH Tyler H. President Logistics and Supply Chain Used the software for: 2+ years ### "Great for a new Broker" November 17, 2020 5.0 We are a 3rd party broker that needed a software to create load confirmations and Invoices. This software perfectly achieves that task and a good price. Pros Over the last 3 years we have had no issues with the software breaking at any point. When I log in I am confident the software will work and allow me to complete the tasks at hand. This is big as down time due to software bugs isn't something that would be acceptable. Cons Minor nuisance, when a repeat carriers liability insurance expires there is no way to make this change within the current dispatch you are working on you most exit and edit that specific vendor and then go back into the dispatch to create the required load confirmation. Reason for choosing Tailwind TMS We are a small office with a limited number of users. We didn't need the multi user accessibility from some of the other more expensive suites and given our existing use of Quickbooks we also didn't need a software at the time of purchase that had a general ledger built in. Review Source Response from Envase December 22, 2020 Hi Tyler, we are glad to hear about your positive experience using the software. We look forward to helping you feel the wind at your back as your company continues to expand! CI Caroline I. Owner Transportation/Trucking/Railroad Used the software for: 1-2 years ### "Daily Use System" December 29, 2021 4.0 Pros We love the ability to follow a load from it's creation, to dispatch, to invoice and remit of invoice. Allows for ease of driver, both o/o and company driver settlements ensuring accuracy. Customer service is great. Cons Occasionally orders are too large to invoice and have to be done manually. Also occasionally invoices mysteriously don't post, however they have worked with us and tried to sort that out. Review Source TM Tiffany M. Operations Manager Transportation/Trucking/Railroad Used the software for: 2+ years ### "Long Time Customer Disappointed in the New Platform" August 26, 2021 1.0 Was a great company when we signed in 2015, now we are just a number and there is no urgency to help us with needed things in the system. Pros Multiple pieces of equipment dispatched with one order. Cons Unable to copy quotes. Features from prior Tailwind software not available in the online platform. No more updates were provided in prior in version basically forcing us to go to the new platform. Reason for choosing Tailwind TMS They have so much history of our data that would have been lost if we went to a new company. Review Source Response from Envase August 27, 2021 Hi Tiffany, We're sorry to learn about your experience. Unfortunately we had to discontinue our legacy application and move to Cloud-based as the market (and staff to support) on-premise is shrinking. We know that changing systems is hard, which is why we continue to support customers on our legacy application even though we haven't sold it in over five years, and in your case, recently provided you with six services hours for specific customizations you required at no charge. I also know that you had recently submitted a feature. As development resources aren't unlimited, we try to implement requests that benefit the greatest number of customers first. Sometimes that means that very specific features for individual customers don't get done right away. Tiffany, as we do for all of our customers, we value your business. We are not saying that won't fulfill the feature request you have asked for - we just have to prioritize it along with requests from other customers. PC Patty C. AccountingSpecialist Transportation/Trucking/Railroad Used the software for: 2+ years ### "Bad " January 4, 2022 1.0 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 Response from Envase 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! CW Christie W. Accountant Transportation/Trucking/Railroad Used the software for: 1-2 years ### "It is a good start to perfect." November 24, 2020 4.0 Tailwind TMS is better than the program we were previously using but it is not exactly how I would like it to be. I look forward to more development of features and programs. Pros The software has made some aspects of the organization and implementation of information and data entry easier and more effective. The developers are always making updates to streamline everything but there is more work to be done. Cons There are some features that don't make sense and others that need to be fixed to be more effective. I wish that we had more control of features and it was easier to get changes made. Review Source Response from Envase December 22, 2020 Hi Christie, thanks for sharing your feedback, we appreciate it! We are always developing more features and updates to ensure our customers are getting the best experience. In fact, since the web-based version of the TMS was launched in November 2016, we've made over 300 updates and enhancements to it! JS Jamil S. President Transportation/Trucking/Railroad Used the software for: 2+ years ### "Best TMS for the Money" February 25, 2022 5.0 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 Response from Envase 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. CM Cole M. Operations Manager Logistics and Supply Chain Used the software for: 1-2 years ### "Great Product" December 3, 2020 5.0 Tailwind is an excellent product that has allowed me to expand in a capacity that would not be managable Pros The product is very easy to use and is packed with many useful features. The ability to track all your orders, drivers, and carriers is very valuable and could not be replicated with just and excel spreadsheet. Cons The ability to create and generate settlements for vendors could be a useful feature. Review Source Response from Envase December 7, 2020 Hi Cole, Thanks for your Tailwind TMS review! To note - we do provide the ability to create payments and the remittance advice acts as a settlement statement for Vendors, showing what they are being paid for. And we also do settlement statements for Owner Ops (some companies consider them as vendors). If you need some assistance with this - you can reach out to our support team via email (support@tailwindtms.com), phone (1-866-441-0441), or through the live chat in the application (where you'll get the fastest response)! Thanks again for your review! Brad from Tailwind SK Sheri K. Dispatch Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Keeps our boys moving" November 17, 2020 3.0 Overall my experience has been alright Pros ease of use for everyday to use in my dispatching. Cons Down time due to online use instead of Software use. Switched from [Tailwind TMS](https://www.capterra.com/p/275384/Tailwind-TMS/) Tailwind Software was not going to be available anymore Review Source RW Ronald W. Sales Manager Transportation/Trucking/Railroad Used the software for: 2+ years ### "Overall review - Scotts transport" December 3, 2020 4.0 Overall the Tailwind software has been very easy to use, and trouble free. Tailwind staff as always been quick to respond to any problems and questions that have come up. Pros Software is very user friendly, and easy to work with , Implementation into to our organization was very smooth, and trouble free Cons would like to see ability to modify data in different modules Review Source Response from Envase December 22, 2020 Hi Ronald, thanks for the feedback, we appreciate it! JW Jeff W. Operations Transportation/Trucking/Railroad Used the software for: 1-2 years ### "Tailwind Review" November 17, 2020 4.0 It gets the job done. Learning has been through application and no real upgraded training takes place. Pros Fairly intuitive to use. Once the basics are learned, it is straight forward. Cons There is no flexibility. For example, there is information I want every day that needs to be put into Excel and then pared down to what I require. Report ideas were submitted but nothing ever happened. Review Source Response from Envase December 22, 2020 Hi Jeff, we appreciate your feedback! As our software continues to evolve, we are looking to implement more customer suggestions, thanks for the review! SA Sheila A. Office Manager Transportation/Trucking/Railroad Used the software for: 2+ years ### "Tailwind TMS" November 23, 2020 5.0 It is easy to use. Pros I love that it integrates with QuickBooks Online. This makes it easy for our accounting side of operations. Cons Occasionally the drivers have problems seeing their load confirmation information. This mostly has to do with our owner/operators. Review Source Response from Envase December 22, 2020 Hi Sheila, thank you for the review! EK Erin K. Owner Logistics and Supply Chain Used the software for: 2+ years ### "Great support, agile platform." January 13, 2021 5.0 Pros We love tailwind and have used it for several years. We would recommend this service to anyone looking for an affordable, highly functional TMS. Cons None! Tailwind is easy to use and fulfills all of our needs. Review Source Response from Envase February 1, 2021 Hi Erin, Thanks for the great review, we appreciate it! kJ kevin J. Vice-President Transportation/Trucking/Railroad Used the software for: 2+ years ### "Tailwind review" December 3, 2020 5.0 Very positive! Pros Helped us expand our business and provide customer data quickly. Easy to use and learn! Cons Didn't integrate with our accounting software. Sage. Review Source Response from Envase December 22, 2020 Hi Kevin, we're happy to help you as your business grows! RB Ricky B. Operations Transportation/Trucking/Railroad Used the software for: 1-2 years ### "Review" November 24, 2020 4.0 This helps us in our day-day operations and provides a one-stop solution for operations and invoicing. Pros Ease of use, practical and intuitive interface. Cons Reporting features are inaccurate are do not seem to be getting fixed. Reason for choosing Tailwind TMS Ease of use Review Source Response from Envase December 22, 2020 Hi Ricky, we appreciate your review and the feedback as we continuously look to make improvements to the software! GS GURPREET S. DIRECTOR Transportation/Trucking/Railroad Used the software for: 1-2 years ### "Best software" November 30, 2020 4.0 Pros The best about Tailwind is about making Invoices Cons Nothing Such is have about the software but just want to learn more about making owner operator invoices as that's bit complicated Review Source Response from Envase December 22, 2020 Hi Gurpreet, thanks for taking the time to leave us a review! DP David P. Owner Translation and Localization Used the software for: 6-12 months ### "Review" November 17, 2020 2.0 This program solves the base problem of needing to send rate confirmations and build shipments but I have yet to think about switching over my quick books due to the incredibly slow speed of the site and multiple crashes per week. Pros Easy to build shipments and understand how to affect the format. Cons The speed of the platform is incredible slow and at least every other day my colleague or myself have the website crash. Review Source BK Bob K. President Transportation/Trucking/Railroad Used the software for: Less than 6 months ### "Customer Support is superb! They develop software targeting user feedback. Best service in my book!" June 3, 2017 5.0 As a startup business I easily completed integration and worked efficiently from day one. The invoicing is very detailed collecting information from the normal workflow of dispatch to billing. Tailwind has developed a very powerful platform with customizable features for any size business. During integration their customer support via live chat that stays with you on each screen is amazing. It's as good as having an in house IT department in your office working on your system all day. Truly amazing customer support. The training videos allows you to continually go back and learn the basics. The way the system operates and the access to training videos, makes on boarding new employees a snap. They basically do it for you with all of the videos. Lynda is the dedicated trainer and she rocks!!!! Pros Dispatch and operation work flow. New order screen has all features on one page. This was created after listening to customer feedback. Their updates happen so fast following feedback, big thumbs up to the development team. Review Source AG Ashley G. Digital Marketing Manager Hospitality Used the software for: 1-2 years ### "Helpful Pinterest Support" April 7, 2019 4.0 We use Tailwind to populate Pinterest pins from website, blog, and social media content. It has been super helpful in tracking pins performance. Pros I love how easy it is to use- simple and worth the time put in for the results. Cons Having multiple team members operate our one account has ha some snags. Review Source JK JAy K. Lead dispatcher Transportation/Trucking/Railroad Used the software for: ### "Easy to use with excellence!! Sophisticated and very well designed!" April 11, 2017 5.0 IN the past, I worked on different dispatch software, however, when I was introduced to TAILWIND, I fell in love with it. It is very user friendly, outstanding technical support, very well organized training with super friendly TAILWIND team, who are always there for you, whenever you need them...........TAILWIND rocks my transport dispatching world! Pros User friendly, excellent technical support, friendly team Cons Nothing I can think of right now Review Source JL Jim L. Operations Manager Used the software for: ### "This software IS awesome!!" May 13, 2016 5.0 We are a small company, it's just me, my emlpoyer and 5 drivers. We just received our authority two years ago. The old software we were using was very tedious and I never heard back from their support department when I needed help. With Tailwind I can punch in 5 dispatches in less than 15 minutes, it used to take me about an hour. I save a significant amount of time using Tailwind. The training is wonderful, I appreciate the Q&A classes and the structure that is available to learn how to use the system. Your trainer is quick to accommodate and can answer all of my questions. Tailwind's support department is incredible, I have a solution to a technical problem within 20minutes they have called me directly instead of sending me emails, making it easier for this old dog to learn new tricks Review Source DV Dean V. Principal Used the software for: ### "I would recomend this program to anyone who is interested in have a user freindly program." May 6, 2009 5.0 I would recomend this program to anyone who is interested in have a user freindly program and a support staff second to none. The cream of the crop as far as support goes. I have never experienced anything as good. Pros This is a very user freindly program. All features are great and can be user altered for their own preferences. Tailwinds provides excellent support and is willing to work to meet your needs. Cons There are no cons to report. Review Source KH Kourtney H. Used the software for: ### "Excellent" May 16, 2016 5.0 We needed a system to make confirmation sheets and were using pen and paper to run our business. I contacted Tailwind and had a demo with Lynda. We got our logins and watched two training videos on our own time. The program was super easy to learn on our own. It was extremely self-explanatory. It took me one month to learn how to use the system. I could have learned it in one week, but I was really busy at work. If I had a question, I got an answer from your support department and your trainer within 1-2 hours. Tailwind stayed in touch with me regularly. I never felt alone in learning how to use the system. Now our business is more organized and I can work from home when I need to. 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