Morton O'Reilly's review of Tailwind Transportation Software

Noble LockmanJan 2026

I've used Tailwind for about a year. Handling our five-truck outfit here in the Pacific Northwest, last month on a Saturday the dispatch board glitched and reassigned a refrigerated load to a driver already two hours into another run - the system even marked the first trip delivered even though the driver never got the pickup, so we missed the rendezvous and the freight had to be rerouted. Support took 36 hours to do anything useful, I had to rebuild paperwork by hand and we ate roughly $1,200 in detention/reload charges while a customer screamed at me. Not worth the headache.

Cassie HoegerJan 2026

Yesterday a driver at a rural yard with patchy service hit upload as soon as he got a bar and the BOL photo popped into Tailwind so fast I’d already started billing before I finished my coffee. The mobile app’s quick uploads and clear status notes shave hours off my day managing 80 trucks on the West Coast, though a few screens can be slow or awkward sometimes.

Orland DibbertJan 2026

…the live GPS map and ETA re-calcs actually saved my skin last week. With 40 trucks and 18 years doing this out of the Midwest, being able to watch minute-by-minute ETAs and reassign a load without a dozen calls cut our chaos in half - wish the pings were a bit more frequent, but that one feature pays for itself.