Tailwind TMS vs TruckingOffice

Motive

AscendTMS

ITS Dispatch

TMS.AI

TruckLogics

E2open

Compare Tailwind TMS and TruckingOffice based on features, pricing, verified reviews, integrations & more on GetApp. Find out which software is best for your business in 2026.

Samsara

Samsara is a fleet operations management platform which helps businesses across various industries including transportation, logistics, and construction streamline fleet operations with features such as GPS fleet tracking, ELD compliance, routing and dispatch, documents, reporting and alerts, and more.

Motive is a cloud-based fleet management solution that helps fleets of all types track vehicles with real-time GPS, automate operations, simplify compliance, and more, using a centralized platform.

One Step GPS

One Step GPS is a web-based fleet tracking solution designed for businesses of all sizes across various industries such as construction, transportation, and service businesses that offers real-time fleet GPS tracking capabilities.  It allows users to monitor the location of their vehicles in real-time and offers vehicle visibility and safety. It helps businesses from asset theft.

No set-up fees. No contracts. Web-based. Free trial, then $99-$199/mth. Manage all dispatches, ops, equipment, accounting & admin. Free mobile ePOD driver app.

3PL Management

Accounting

Billing & Invoicing

Carrier Management

Communication Management

Contact Database

Customer Database

Customer Management

Customer Portal

Data Import/Export

Dispatch Management

Driver Management

Driver Settlements

Fleet Management

For Freight Operations

Fuel Management

Historical Reporting

Import/Export Management

International Forwarders

Live Driver Tracking

Load Optimization

Local Forwarders

LTL/Shared Truckload

Maintenance Management

Maintenance Scheduling

Mileage Tracking

Mobile App

Order Management

Order Tracking

QuickBooks Integration

Quotes/Estimates

Rate Management

Real-Time Notifications

Reporting/Analytics

Route Management

Routing

Scheduling

Shipment Tracking

Third-Party Integrations

Transportation Management

Trip Logs

Truckload Management

Vehicle Management

Waybills

Tailwind TMS

Web-based

Android

Windows

iPhone

iPad

Linux

Chromebook

Enterprise

Unlimited

Operation - Dispatch Lead

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

Dispatcher

Easy to find an order and create a dispatch and save the POD and BOL and enter the cost associated with the load

Operations Manager

Many others do the same thing for far less, and with better customer service.

Owner 

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.

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.

Vice President

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.

Owner

Also occasionally invoices mysteriously don't post, however they have worked with us and tried to sort that out.

Poor transaction history and being able to see who did what in the system.  

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 Product is an easy-to-use TMS and I've used others similar in the past.

No more updates were provided in prior in version basically forcing us to go to the new platform.

Dispatch

Drivers dont have to send emails or let us know when they check in or check out.

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.

The accounting is a bit difficult along with multi stop trips

Operations

This helps us in our day-day operations and provides a one-stop solution for operations and invoicing.

The ability to track all your orders, drivers, and carriers is very valuable and could not be replicated with just and excel spreadsheet.

AccountingSpecialist

It states that it was sent but a lot of the times it does not make it to the customer.

Manager

I have been able to train people remotely which is necessary at this time.

Director of Transportation

What I like the least from the software is that the drivers App doesn't show enough information for the pickups and deliveries.

Accountant

They make things ease out for themselves when transfer to the new version.

Great reports, and you can store files on trucks, drivers, and all your exp data.  

The software also lacks the ability of end-user customization of documents and the interface.

Additionally, there should be an integrated GPS for truck routes to avoid non-commercial routes, low bridges, and tight intersections.

President

We are a 3rd party broker that needed a software to create load confirmations and Invoices.  

The software has made some aspects of the organization and implementation of information and data entry easier and more effective.

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.  

Keeps our customers informed as well which is great

USA transport manager 

If this change was made it would be excellent software but until then it takes way to many clicks and to much time to build loads.

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.

manager

The ability to customize the software and make changes

Using tailwind has really cut down the amount of time spent each month on administrative tasks.

Safety Coordinator

All these were not available with the last program we used but we did not have a dispatch program prior to Tailwind.

The price point is a little high considering the lack of GPS and driver's app functionality.

Office Manager

Occasionally the drivers have problems seeing their load confirmation information.

Sales Manager

would like to see ability to modify data in different modules

It is affordable software and customer service is good.

No admin app for viewing platform on tablet/phones.  

Director Finance

It does everything you need in terms of a transportation management system.

Vice-President

Helped us expand our business and provide customer data quickly.  

proprietor

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

The long turn around time on errors or fixing bugs/problems

There is a few extra steps when importing to Quick Books

ACCOUNTING ASSISTANT

Very easy to use and to train new staff to use.

logistics coordinator

Reporting could use some adhoc capabilities.

Reporting features are inaccurate are do not seem to be getting fixed.

Customer Support

Customizability

Invoicing

Accounting and Tracking

Training and Learning Curve

Reporting

Tailwind

Ease of Use

201-500

1000+

2-10

Self-Employed

Envase

TruckingOffice is a web-based trucking management solution that helps businesses in the transportation industry manage deliveries, record expenses, & file IFTA

Accounting Integration

Activity Dashboard

Automated Scheduling

Delivery Tracking

Employee Management

Geographic Maps

Inspection Management

Inventory Management

Monitoring

Preventive Maintenance

Reporting & Statistics

Route Optimization

Shipping Management

Status Tracking

Tire Management

VIN Lookup

Work Order Management

TruckingOffice

Basic

Some reports are not available , such as isolating the revenue done with a certain customer

There are a lot of pertinent features that are missing from this software that is needed for the trucking community.

Tailwind TMS vs TruckingOffice Comparison (2026)

Tailwind TMS

TruckingOffice

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