# Page 2 | Tailwind TMS Reviews 2026. Verified Reviews, Pros & Cons | Capterra

> Page 2 - 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

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Tailwind TMS

4.2 (97)

[View alternatives](https://www.capterra.com/p/275384/Tailwind-TMS/alternatives/)

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Last updated March 13th, 2026

# Page 2 - Reviews of Tailwind TMS

## Showing most helpful reviews

Showing 26-50 of 97 Reviews

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Most Helpful

Rating

Company Size

Reviewer's Role

Length of Use

Frequency of Use

M-JS

Martin - John S.  
Operation - Dispatch Lead  
Logistics and Supply Chain  
Used the software for: 6-12 months

### "Operation Manger and lead dispatch "

December 11, 2024

1.0

Originally hey this is pretty good but since there so called update or new platform its gone to crap. Getting service is terrible def wouldn't recommend it to anyone anymore

Pros

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

Cons

Customer service is almost non existent they want you to go to a \[portal now set up a account and send in requests for service that way. Terrible option took a decent product right down to crapper when they did this. Its stalling more and more and we have to refresh 15-20 times a day just always waiting for it to go to next step very slow.

Review Source

RA

Richard A.  
EVP  
Transportation/Trucking/Railroad  
Used the software for: 2+ years

### "Product quality"

December 3, 2020

3.0

For our current size, it has checked the most important boxes. Critical Dispatch, billing, AR mgmt functions are covered for the most part. If we continue our growth we will have to migrate to a different platform without some developments on Tailwinds side. For reference, our we are a 45 truck fleet.

Pros

Easy to navigate. Web based platform. Reasonably committed to product improvement and feedback from end users.

Cons

Lacking integrations with outside vendors (specifically ELD platforms, EDI platforms, Load boards and tracking softwares). POD complete app is functional, but has issues with format and size of file when transferring to customers for invoicing. Seems like they could partner with a transflo or some other software that already has the software built to strengthen their offering. No admin app for viewing platform on tablet/phones. Reporting could use some adhoc capabilities.

Alternatives considered

[AscendTMS](https://www.capterra.com/p/122488/AscendTMS-Logistics-Software/)[Prophesy, a Körber product](https://www.capterra.com/p/180560/ProphesySeries-Internet-Shipment-Tracking/)

Reason for choosing Tailwind TMS

Price, ease of use, ease of transition.

Review Source

Response from Envase

December 29, 2020

Hi Richard, Thanks for your review and the feedback! Our recent partnerships with Kleinschmidt (EDI), EZ-Track and Trucker Tools (tracking) should help address some of your integration needs, and there's also an upcoming integration with Samsara (ELD) that will be announced officially soon! And there are more integrations slated for 2021 :-)

FL

Frank L.  
Director of Transportation  
Automotive  
Used the software for: 6-12 months

### "Transportation Software for an Auto Auction"

December 3, 2020

4.0

Overall, I researched numerous Transportation Apps and this one had the best features for our industry. It seems more suited to brokers than an auto auction but it works well. The customer service has been exceptional. The price point is a little high considering the lack of GPS and driver's app functionality.

Pros

What I liked most about the software is that it is very versatile. It tracks everything for us from pickups and deliveries. For the first time, we are able to quantify the value of transportation in a market of ever-changing agreements and pricing.

Cons

What I like the least from the software is that the drivers App doesn't show enough information for the pickups and deliveries. Also, there is no GPS integration for the drivers. With other Apps, drivers can just press the address and it automatically sends them to Google maps or Waze. Additionally, there should be an integrated GPS for truck routes to avoid non-commercial routes, low bridges, and tight intersections.

Reason for choosing Tailwind TMS

Tailwind was the most comprehensive App on the market that I researched. I did over a dozen webinars with different companies and I finally settled on Tailwind. It's not perfect, but it has a lot of advantages for our company and industry.

Switched from

[Towbook Management Software](https://www.capterra.com/p/94188/Towbook-Management-Software/)

The towbook app was great except that we couldn't clearly distinguish from pickups and deliveries. It was only $200 a month. Sometimes the App would crash holding our work hostage for an entire day.

Review Source

Response from Envase

December 29, 2020

Hi Frank, Thanks for your review and the feedback! We will update our development team with your suggestions to see what changes may need to be made. Our integration with EZ-Track also provides you with free load tracking--25-loads tracked in our Pro tier, 50 in Enterprise, and unlimited tracking in our Unlimited tier!

DK

Djuro K.  
Ceo  
Transportation/Trucking/Railroad  
Used the software for: I used a free trial

### "Tailwind TMS is the best you will find and love !!!!"

January 9, 2021

5.0

Great software, but just that driver app needs work.

Pros

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. Software has all the things you can think of. Great reports, and you can store files on trucks, drivers, and all your exp data. 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. You can easly export documenta as 1 file for your factoring. There is many many grest things. POD Complete is free.... Other simular solutions charge 7-25,000$ Down payment and 800-1300 a month. Plus 10-20$ for a driver app.

Cons

Now, yes there is cons, One is sometimes its slogish and it takes a bit to load but not that bad. The other one, POD Complete , well its a little incomplete, it has the options you need, you send the laod and driver can arrive depart, great, attach POD its there but, it needs work, this needs to have transflo options or something like a camsxanner, just to let you cut the page adjust it before you send it over. Plus it would take lot less storage if it was a scan doxument, this way its a picture, not that great for billing, it does work. But I think tailwind shoudl stop all other areas of development cuz they are great and spend some time here, make this app a killer. Evan charge 10$-20$ a driver /mo I would pay it just to get a better app. It needs to have scan features, we all need to get those Bols in good quality, and we dont want to have to use translfo or camscaner or other apps and than have to import the documents into tailwind.

Review Source

Larry F.  
Owner  
Transportation/Trucking/Railroad  
Used the software for: 2+ years

### "Tailwinds is my office support staff "

December 6, 2018

5.0

My company has made great advances because the software allowed me to have good record keeping and dispatches with information not having all the extra paperwork in files but only the backups. Efficiency of what this has allowed me to do by giving me the time. can do the work of 3 people

Pros

There are many features that make it the ease of taking little time for paperwork when doing dispatch and keeping track of loads. You will have information on Loads, Customers, Vendors at your fingertips There is a superb support staff that is there to help.

Cons

I have a hard time finding something i don't like Are there some that could improve? Yes and they have worked on them and made them 100%

Review Source

KB

Katherine B.  
Owner  
Transportation/Trucking/Railroad  
Used the software for: Less than 6 months

### "NOT happy with support!"

November 30, 2020

2.0

i am not happy with it. I think it is super expensive for the service we are getting!

Pros

At the beginning I liked the ease of use and the customer service however over the past month, I have been VERY unhappy with the software. \*Customer support is AWFUL! 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 \*Issues with printing cheques, this is wasting alot of my time, it is taking me 10 times longer than it did with my previous system

Cons

the "accounting side" of the system, it doesn't work at ALL! customer service

Switched from

[TransPlus](https://www.capterra.com/p/85105/Fleet-Manager-Professional/)

Thought your system had more functions and easier to use but it turns out it does in some areas but others, it's AWFUL!

Review Source

Response from Envase

December 1, 2020

Hi Katherine, I'm disappointed to hear about the apparent poor service you report to have received from Tailwind. We do really pride ourselves on providing prompt and full support - which is why we keep it in-house rather than offshoring. I have reviewed the latest set of conversations you have had with the Tailwind Support team, and it appears that a solution for your issues has been found (and thank you for the latest 'Amazing' conversation rating you provided!). That said - our goal at Tailwind is to provide you with a transportation management system that will allow you grow your business - and ideally, give you a bit more time at the end of your day) - so if you do require additional support - please do reach out (support@tailwindtms.com; 1-866-441-0441).

Jason D.  
President  
Transportation/Trucking/Railroad  
Used the software for: 2+ years

### "Best TMS Software"

November 23, 2020

5.0

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.

Pros

This software is so easy to use and intuitive. It can be used anywhere and has the features that other softwares charge 10+x the amount for.

Cons

Each new device you use the software on, you have to reset the setting, but not something that happens very often. Minimal cons to this software.

Review Source

Response from Envase

December 22, 2020

Hi Jason, thanks for the great review!

PK

Peter K.  
Director Finance  
Transportation/Trucking/Railroad  
Used the software for: 2+ years

### "Using Tailwind"

November 23, 2020

5.0

Great experience. Easy to use and support is at your fingertips with high quality videos tutorials. technical support is very responsive should you require assistance.

Pros

Web based interface with proven stability is a key factor to the Tailwind Product. It does everything you need in terms of a transportation management system.

Cons

No ability to tap into the database and create custom reporting on your own without creating an expensive API.

Switched from

[Sage 50 Accounting](https://www.capterra.com/p/174753/Sage-50cloud/)

Gain the ability to track our loads and as well as our drivers. The POD features are important as well.

Review Source

Response from Envase

December 22, 2020

Hi Peter, thank you for the review. Our new Unlimited tier that we launched in September includes API web-hooks which might help.

Daniel T.  
New Business Development Manager  
Import and Export  
Used the software for: 6-12 months

### "Tailwind Review"

January 21, 2019

5.0

great TMS , it can handle my loads very easy, is the only software that I know , than can handle an international load, taking a mexican carrier, with their own trailer number, involve a wharehouse , transload the product to a US carrier with a different trailer number , and give you the avaibility to track the load in one single order, not just that, it also provide indivual instructions and BL for each party, and receive the invoice for each carry involve so payments for each of them can be done with the proper administration, and for you customer can get togther all this job and send them just one invoice for the all service... this TMS is great

Pros

Is very flexible and you are able to creat the orders as you want

Cons

Traying to get automatic commsion payments for your personel can be tricky but once you get it done works great

Review Source

Response from Envase

January 22, 2019

Thanks Daniel - we appreciate the feedback!

GH

Genevieve H.  
Safety Coordinator  
Transportation/Trucking/Railroad  
Used the software for: 1-2 years

### "Could be better"

November 23, 2020

4.0

Pros

Being able to look back at any information, finding everything a particular truck/driver/trailer did for a certain time period. It has a lot of reports. All these were not available with the last program we used but we did not have a dispatch program prior to Tailwind. Tailwind is user friendly once you get to know your way around.

Cons

Support could be better, we have requested some add ons a few months ago and we've had no word on when this would take place. Some of the changes made by Tailwind seemed unnecessary and caused more issues for us.

Review Source

Response from Envase

December 22, 2020

Hi Genevieve, thanks for the feedback! We will take a look into your suggestions to see what changes need to be made in order to provide an optimal experience. Our support team is usually very responsive especially in the in-app chat, so we will review what happened there.

LS

Lucy S.  
Accountant  
Transportation/Trucking/Railroad  
Used the software for: 2+ years

### "Cost Effective"

September 11, 2021

4.0

Very nice person and good customer service. But frustrated when you lost some important features in the previous version and make it more difficult to track your operation result ; and they do not provide the option to generate a new report even if all the data are in the a table. However, if your business is not involved complexity transactions, the functions maybe good enough for you.

Pros

It is affordable software and customer service is good.

Cons

Week on software developer side. They make things ease out for themselves when transfer to the new version.

Review Source

PL

Pamela L.  
Gen Mgr  
Transportation/Trucking/Railroad  
Used the software for: 2+ years

### "Tailwind is great!"

June 20, 2016

4.0

Our initial experience with Tailwind was a little "rough". However, John and Kyle worked with us and saw us through our implementation problems. What I really like about Tailwind is the support. The support team is responsive and appropriately reactive. With respect to the program, it is organized and user friendly. We broker in our business and had tried some demos with other transportation management systems but they didn't fit as well as Tailwind has. Tailwind makes our work more efficient, there are fewer mistakes made as you only have to enter the data once and we can see the process through to billing. Tailwind has helped our business to grow and become more profitable.

Pros

Data only needs to be entered once Fewer errors Allows tracking of previous loads so you can look at history to help with the future loads

Cons

There are a few bugs we are ironing out.

Review Source

TG

Tim G.  
proprietor  
Logistics and Supply Chain  
Used the software for: 2+ years

### "Canadian shipping"

November 17, 2020

5.0

I dont use a lot of the features offered, because I do most accounting old school.

Pros

produces professional documentation, data base development grows with your company.

Cons

Some edits example adding Trailer types. Can be difficult for us less than computer savvy users

Reason for choosing Tailwind TMS

Tailwinds offers me ease of use, Tailwinds is industry recognized.

Review Source

Response from Envase

December 22, 2020

Hi Tim, thanks for your review! It's great to know we can assist you as your company grows, and we are continuously working on ways to make it more and more user friendly and intuitive.

PK

Paul K.  
Office Manager  
Logistics and Supply Chain  
Used the software for: 2+ years

### "Tailwinds Is a Game Changer!!!"

November 17, 2020

5.0

This has been a great asset to our business and we would not be where we are today without Tailwinds helpiong us with orders/invoices/AP/AR

Pros

We found this programvery user friendly, and having an online based software is amazing, as well as Tailwinds Customer service. They are there for you at a moments notice because of their live chat option.

Cons

Some integrations with QuickBooks can be confusing. But once you get a feel for how the two programs work together it becomes easier

Review Source

Response from Envase

December 22, 2020

Hi Paul, thanks for your review! We are glad you found the software user friendly!

AB

Andrew B.  
Operations  
Logistics and Supply Chain  
Used the software for: 2+ years

### "Day to day operations"

November 30, 2020

4.0

Pros

Tailwind for the price is very easy to use, easy to teach and operate.

Cons

Certain small features I wish could be customized. Such as the quantity description. The one option that it does not list which we use all the time is seats or cubes. Another option I would like to see is another check box when a driver is dispatched.

Review Source

Response from Envase

December 22, 2020

Hi Andrew, thanks for sharing your suggestions. As a software that continuously adds enhancements and updates to provide excellent experiences, we appreciate your feedback!

SO

Scott O.  
Owner/President  
Transportation/Trucking/Railroad  
Used the software for: 6-12 months

### "Powerful Tool - And Slow"

January 14, 2019

3.0

Lehmans terms could assist with training new people on the software.

Pros

It has a lot of bells and whistles which we find are useful, from payroll to Quickbooks integration. Support is responsive Monday - Friday.

Cons

Very slow, we used multiple browsers, Mac and Windows, in addition we have used several wifi points to ensure it was not our internet. We compared this TMS to some other online trials and these systems responded much better. Concern Tailwinds may be a thing of the past for us, we are a fast moving business and the product is becoming a thorn in our side.

Review Source

Response from Envase

January 18, 2019

Hi Scott. We are sorry to hear you are experiencing slowness with your application. I see that some adjustments were made to your system a few days ago which hopefully should have helped. Regardless, we will be in touch to help rectify the problem.

DA

Devon A.  
Owner  
Transportation/Trucking/Railroad  
Used the software for: 6-12 months

### "Awesome software for the small to mid size operation"

September 6, 2019

5.0

none, They are fantastic

Pros

Super easy to learn and use. I I am the only one in the office and wear many different hats when it comes to running the company and this software put all the info i need at my fingertips. It is super easy to have an asset based operation and have a brokerage operation and run them on the same screen. It is also super easy to move a load from the one division to another as needed.

Cons

A maintenance module that tracks the service schedule of the equipment would be nice so it is in one package

Switched from

[Dr Dispatch](https://www.capterra.com/p/79334/Dr-Dispatch/)

Desktop based and very unfriendly

Review Source

JH

Jordan H.  
USA transport manager  
Transportation/Trucking/Railroad  
Used the software for: 1-2 years

### "Too many clicks "

November 17, 2020

3.0

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.

Pros

Not sure. It needs to be made more efficient.

Cons

Creating a shipment. Way to many windows and clicks. There should be one window to add in POs etc not several different. It consumes a lot more time than needed. I’ve mentioned this to support before but they didn’t seem to care

Reason for choosing Tailwind TMS

Not sure

Review Source

Response from Envase

December 22, 2020

Hi Jordan, we appreciate your feedback! We are continuously looking to improve and produce quality software for our customers. We take pride in providing exceptional customer service and support so we will be reviewing the interactions you had with our team.

JS

John S.  
Accountant  
Transportation/Trucking/Railroad  
Used the software for: 1-2 years

### "Tailwinds rating review"

June 17, 2016

4.0

We started with Tailwinds in 2013 and found that the software developed our internal system to where we could increase both dispatchers and accounting efficiencies. Working together with Tailwinds, we've increased our business significantly without any development problems with the volume increase.

Pros

It efficiency handles booking and costing of loads, has good credit capabilities built in for reference of potential credit issues, reporting is good with most being able for export to Excel if further analysis is needed, and the cost is reasonable for well working software.

Cons

Sorting capabilities should be based on more than one criteria. This would probably be an easy fix with TW software people. Clients should get a workshop how to build report generators tailored to their business needs rather than requesting TW software team to built it.

Review Source

PS

Paul S.  
Owner  
Logistics and Supply Chain  
Used the software for: 2+ years

### "End User"

December 29, 2021

4.0

Pros

The software is straight forward and easy to use.

Cons

Not enough customization is available. There are a few features that I would like to be able to customize, that I am not able to.

Review Source

Francois D.  
President  
Logistics and Supply Chain  
Used the software for: 2+ years

### "Do not recommend"

August 28, 2025

1.0

Pros

Friendly user, easy setup, cloud based TMS system. Clean and effective system. Easy to use and train new staff to use.

Cons

Ever since Tailwind was sold to a US based company, the support is almost unexistent. We sometimes have to wait over 24 hrs only to get an answer, sometimes up to a week to get resolution. As an example, Vendor pay list has not been working for 48hrs, therefore unable to pay my carriers. Very frustrating. Planning to change to another TMS system very soon.

Review Source

AK

Ashveen K.  
Dispatcher  
Transportation/Trucking/Railroad  
Used the software for: Less than 6 months

### "Review for TAILWIND TMS"

August 29, 2022

5.0

Very satisfactory and easy to navigate around

Pros

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

Cons

Based on the internet connection sometimes it slow to load the information on the page or top open a file

Review Source

Response from Envase

September 6, 2022

Hi Ashveen, thank you for your review and feedback. It's great to hear that Tailwind has made dispatching an easier and seamless process for you! Our development team is always working to improve the user experience, so even though internet speed is out of our hands, we will keep an eye on the backend to see if there is anything we can do to improve page load speed :)

BS

Brian S.  
Owner  
Transportation/Trucking/Railroad  
Used the software for: 1-2 years

### "Usage"

December 3, 2020

3.0

Pros

I used the old version, much more user friendly. This package is very difficult to use.

Cons

not user friendly, too many obstacles at every corner.

Reason for choosing Tailwind TMS

Used it at another brokerage, (old version). This new version is bad

Review Source

Response from Envase

December 29, 2020

Hi Brian, thanks, the feedback! We're sorry to hear you're having troubles switching from the on-premise to online Tailwind TMS. While switching to a new system is rarely easy, we do offer in-app support, free online training sessions and demos, and even free 1-1 'health-checks' to make sure you're able to get the most of the software.

JO

Jack O.  
Director of Sales and Ops.  
Transportation/Trucking/Railroad  
Used the software for: 2+ years

### "Irish Review"

December 3, 2020

5.0

I have been very pleased with Tailwind. Overall it is very user friendly and the staff is very responsive when I am needing assistance. It has all the features that we need as a 3PL user.

Pros

User Friendly, Integrations, adapting to our needs.

Cons

Quickbooks implementation, Speed of software at times.

Review Source

Response from Envase

December 22, 2020

Hi Jack, thanks for your review! We're glad to assist you!

AM

Andrew M.  
Branch Manager  
Transportation/Trucking/Railroad  
Used the software for: 1-2 years

### "Good value for money"

November 17, 2020

5.0

If you are on the go all the time, since Tailwind is web based, you can login on your laptop when on the road. Tailwind offers a paperless environment.

Pros

I like the fact that we can use multiple currency. This makes it easy to do business with both American and Canadian customers

Cons

When you create a LTL shipment with different skid dimensions, you are unable to input the different sizes

Reason for choosing Tailwind TMS

Good product, good customer support.

Review Source

Response from Envase

December 22, 2020

Hi Andrew, thank you for taking the time to leave us a review!

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