--- title: "Tailwind TMS Software Pricing, Alternatives & More 2026 | Capterra" description: "With the help of Capterra, learn about Tailwind TMS Software - reviews, pricing plans, popular comparisons to other Transportation Management products and more." source_url: "https://www.capterra.com/p/275384/Tailwind-TMS/" page_type: "product" language: "en" publication_date: "2026-10-19" --- # Tailwind TMS Software Review 2026: Features, Integrations, Pros & Cons Last updated on October 19, 2026 Provider data verified by our Software Research team, and reviews moderated by our Reviews Verification team. [Description](#description)[Use cases](#use-cases)[Alternatives](#alternatives)[FAQs](#faqs)[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 Free version not included 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://www.g2.com/products/tailwind-tms/claim_requests/new?auto=true) ## 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. [4.5 (1,689)](https://www.capterra.com/p/138669/Motive/reviews/) Starting Price $99 Per User, Per Month Starting Price Contact vendor Free Trial Free Version Pricing Options Free Trial Free Version Ease Of Use 4.2 (97) Ease Of Use 4.4 (1,068) Value For Money 4.2 (61) Value For Money 4.2 (1,003) Customer Service 4.5 (96) Customer Service 4.4 (1,013) ## Tailwind TMS alternatives [4.2 (248)](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 Highest Rated [4.7 (388)](https://www.capterra.com/p/131389/Elite-EXTRA/reviews/) Starting price $35.00 Per User, Per Month Pricing Options Free Trial Free Version User Rating 97% of reviewers rated it above 4 stars [4.4 (100)](https://www.capterra.com/p/18289/MyGeotab/reviews/) Starting price Contact vendor for pricing Pricing Options Free Trial Free Version User Rating 85% of reviewers rated it above 4 stars [3.7 (38)](https://www.capterra.com/p/175186/Transportation-Management-and-Trucking-Software/reviews/) Starting price Contact vendor for pricing Pricing Options Free Trial Free Version User Rating 68% of reviewers rated it above 4 stars [View all alternatives](https://www.capterra.com/p/275384/Tailwind-TMS/alternatives/) ## FAQs about Tailwind TMS Overview ### What problems does Tailwind TMS solve? Tailwind TMS solves lost orders, fragmented load tracking, duplicate data entry, and disconnected billing workflows for transportation businesses. Dispatchers, brokers, operations staff, and accounting teams can track pickups, deliveries, multi-stop loads, payables, receivables, costs, and invoices in one system, while using reports and load history to monitor financial performance. Answer based on 24 reviews Overview ### Which roles and teams benefit most from Tailwind TMS? Tailwind TMS is most used by transportation company owners, presidents, and general managers who need visibility into fleet activity, profitability, and daily operations. Operations managers and dispatch teams coordinate loads, drivers, and delivery schedules, while accounting staff and controllers manage invoicing, settlements, and financial records. Answer based on 94 reviews Overview ### What company size and industries is Tailwind TMS built for? Tailwind TMS is designed for growing OTR trucking companies and freight brokerages, with 97% of reviewers from small businesses. It primarily serves Transportation/Trucking/Railroad organizations (78%) and Logistics and Supply Chain companies (16%), while midsize businesses represent 3% of reviewers and Automotive accounts for 1%. Answer based on 97 reviews Features and Usability ### What are the key features of Tailwind TMS? Tailwind TMS includes core transportation management features for order management, dispatching, shipment tracking, and costs, plus accounting features for billing and invoicing. Additional core capabilities include EDI, equipment maintenance, mobile app access, and quotes. It also supports carrier, driver, and customer records for freight operations. Answer based on 53 reviews Pricing ### How much does it cost and what fees or limitations are included? Tailwind TMS offers Pro at $99 per user/month, including 25 loads monthly, while Enterprise (50 loads) and Unlimited (unlimited loads) cost 149 and 199 per user/month. All plans include a free trial. Reviewers often call it affordable, though some report high additional-user costs or expense for smaller companies. Answer based on 13 reviews Integrations ### Which third-party tools and platforms does Tailwind TMS integrate with? Tailwind TMS integrates with 7 third-party tools, including Descartes MacroPoint, EZCheck-In, EZTrack, Google Maps, Kleinschmidt, QuickBooks Online Advanced, and Samsara. These integrations cover tracking, check-in, mapping, customs, accounting, and fleet visibility within the platform. Answer based on 6 reviews Getting Started and Support ### How easy is it to onboard and train a team on Tailwind TMS? Tailwind TMS offers in-person and live online training, webinars, documentation, and videos. Reviewers say dispatchers, small teams, new hires, and users with limited computer experience often learn the basics quickly. Administrators or teams adopting broader workflows may need several weeks and additional support to understand reporting, configuration, and advanced features. Answer based on 31 reviews Getting Started and Support ### What customer support options does Tailwind TMS offer, and how do users rate the experience? Tailwind TMS offers email/help desk, FAQ/forum, knowledge base, phone support, 24/7 live representative assistance, and chat. Many users report prompt, helpful guidance and clear explanations, including quick technical issue resolution. Some users, however, describe slower service after platform changes, portal-based requests, and difficulty reaching a person for urgent concerns. Answer based on 53 reviews Accounting and tracking ### How well does Tailwind TMS handle accounting and load tracking? Tailwind TMS combines load tracking, billing, payables, receivables, and reporting in one transportation management system. Freight brokers and growing carriers value centralized order history, detailed invoices, and accounting integrations, while some teams find accounting workflows, multi-stop trips, audit history, and ad hoc reporting less flexible than expected. Answer based on 24 reviews ## Features AI summary Based on 954 Transportation Management reviews Capterra reviewers highlight these as the features buyers value most when choosing transportation dispatch software: - **Billing & Invoicing** (**60%** of reviewers rated this feature as critical) - **Dispatch Management** (**58%**) - **Delivery Tracking** (**58%**) Tailwind TMS supports **Dispatch Management** and **Billing & Invoicing**, so teams can assign loads efficiently and manage customer charges and payments in one system. However, it does not offer **Delivery Tracking**. Instead, it provides **GPS** (**53%**), which still gives dispatchers better visibility into vehicle location and movement. Together, these features help businesses coordinate daily operations, improve billing accuracy, and keep teams informed while freight is in transit. 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 Dispatch Management 3.0 (1) 0.00% of 1 reviewers that rated this feature as important or highly important Manage sending personnel and resources to a site as needed GPS 3.0 (1) 0.00% of 1 reviewers that rated this feature as important or highly important System to support the positioning, navigation, and timing (PNT) measurements of an object or individual 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 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 Tailwind TMS 53 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. Analyze overall costs for vehicle maintenance, fuel consumption and mileage 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 Track maintenance operations for the products sold, such as calibration or preventive maintenance 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 Process of familiarizing new clients, stakeholders or employees with the company, a new location, or a service Manage and track customer orders for goods, investments, or any other purchases Track orders throughout the fulfillment process Provide standard pricing options that can be customized by customer. Integrates with QuickBooks Create and manage personalized quotes for freight services. 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 Track shipments from warehouse to the destination, including drop shipments and multilocation shipping. 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/)[ Samsara](https://www.capterra.com/p/167543/Samsara-for-Fleets-0-00-6-23/)[ QuickBooks Online Advanced](https://www.capterra.com/p/189398/QuickBooks-Online/)[ 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 Counts reflect reviews available in this feed. 5(50) 4(31) 3(10) 2(2) 1(4) Mentioned topic Recent reviews first, then most helpful RE Reviewer Vice President Used the software for: 1-3 years ### "Powerful Tool for Small to Medium Trucking Operations." 3.0 Overall Rating 3.0 3.0 Ease of Use 3.0 3.0 Features 3.0 3.0 Customer Service 5.0 5.0 Likelihood to Recommend 7/10 November 18, 2020 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. 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. RE Reviewer Manager Used the software for: 3-5 years ### "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 6, 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. 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. RE Reviewer Operations Manager Used the software for: 3-5 years ### "Operations Manager" 4.0 Overall Rating 4.0 4.0 Ease of Use 5.0 5.0 Features 2.0 2.0 Customer Service 3.0 3.0 Likelihood to Recommend 5/10 December 24, 2021 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 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. RE Reviewer President Used the software for: 3-5 years ### "Great for a new Broker" 5.0 Overall Rating 5.0 5.0 Ease of Use 4.0 4.0 Features 5.0 5.0 Customer Service 5.0 5.0 Likelihood to Recommend 8/10 November 18, 2020 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. 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. RE Reviewer Owner Used the software for: 1-3 years ### "Daily Use System" 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 9/10 December 30, 2021 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 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. RE Reviewer Operations Manager Used the software for: 3-5 years ### "Long Time Customer Disappointed in the New Platform" 1.0 Overall Rating 1.0 1.0 Ease of Use 2.0 2.0 Features 1.0 1.0 Customer Service 1.0 1.0 Likelihood to Recommend 1/10 August 27, 2021 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. 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. RE Reviewer AccountingSpecialist Used the software for: 3-5 years ### "Bad " 1.0 January 6, 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 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. RE Reviewer Accountant Used the software for: 1-3 years ### "It is a good start to perfect." 4.0 Overall Rating 4.0 4.0 Ease of Use 5.0 5.0 Features 3.0 3.0 Customer Service 5.0 5.0 Likelihood to Recommend 8/10 November 25, 2020 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 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. RE Reviewer President Used the software for: 3-5 years ### "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 March 2, 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 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. RE Reviewer Operations Manager Used the software for: 1-3 years ### "Great Product" 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 December 4, 2020 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 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. [View all Reviews](https://www.capterra.com/p/275384/Tailwind-TMS/reviews/) ## Top-rated software of 2026 ### Fill out the form and we'll send a list of the top-rated software based on real user reviews directly to your inbox. Popular comparisons [Samsara vs Tailwind TMS](https://www.capterra.com/compare/167543-275384/Samsara-for-Fleets-0-00-6-23-vs-Tailwind-TMS)