# Windward System Five Pricing 2026 | Capterra > Learn more about Windward System Five pricing plans including starting price, free versions and trials. Source: https://www.capterra.com/p/43189/Windward-System-Five/pricing --- # Pricing for Windward System Five [3.8 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) Write a Review! ## [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/) has **3** pricing plans - No free trial - No free version **Credit Card Required:** No ### System Five on Cloud with Partner Processing $135 **Pricing Model:** Per User **Payment Frequency:** Per Month System Five on Cloud with Partner Processing plan includes: - 24/7 Live Customer Support - 2-Factor Authentication - Secure Cloud Backup - Updates Included - Windward Intelligence ### System Five on Cloud Standard $149 **Pricing Model:** Per User **Payment Frequency:** Per Month System Five on Cloud Standard plan includes: - 24/7 Live Customer Support - 2-Factor Authentication - Secure Cloud Backup - Updates Included - Windward Intelligence ### System Five on Cloud Monthly $179 **Pricing Model:** Per User **Payment Frequency:** Per Month System Five on Cloud Monthly plan includes: - 24/7 Live Customer Support - 2-Factor Authentication - Secure Cloud Backup - Updates Included - Windward Intelligence ## Popular alternatives to [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/) Looking to learn more about Retail Management Systems software similar to Windward System Five? 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Value For Money[3.6(189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) Pros Cons [Read All 189 Reviews](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) Read Full Reviews Below Mason B. Sales Associate Consumer Goods, 1-10 employees Used the software for: 1-2 years ** Overall Rating 4.0 ** Ease of Use 4.0 Features 4.0 Likelihood to Recommend 60% 6/10 Reviewer Source Source: Capterra August 1, 2025 "Slightly outdated, but intuitive and powerful" **Overall:** My overall experience was positive, and still is to some extent, though we largely use System Five as a database for older customer information now. Searching for historic records of customer purchases, inventory tracking over time, and loyalty program points still works very well. **Pros:** Good value, and capabilities of software were far more advanced than I was expecting. Capable with inventory tracking, private customer data management, and invoicing. **Cons:** An outdated and clunky UI makes it much harder to utilize to its full capabilities, occasional long loading times, and annoying notifications about users connected to different pieces of hardware. Greg H. Owner Retail, 1-10 employees Used the software for: 2+ years ** Overall Rating 1.0 ** Ease of Use 4.0 Customer Service 1.0 Features 5.0 Value for Money 1.0 Reviewer Source Source: Capterra June 18, 2025 "My goodness do not buy this software." **Overall:** Please please please save yourself - DO NOT buy into this software. It looks so good from the outside but once you're working in it every day, nothing works the way it is supposed to. It would appear that no one at Windward has EVER used the software for any length of time because bugs and usability issues persist for all eternity. Development is out of control - one developer in one area will fix something but that will break 4 other things in other areas. Developer 2 will fix what developer 1 broke, but it re-breaks the original problem. Rinse and repeat forever. From one of System 5's oldest customers - stay out of this swamp! **Pros:** Extremely versatile and powerful. If you want to do something, System Five probably does it. The interface is good, we host on premises so performance is generally OK (after 20+ years our dataset is getting big and some reports are slow.) **Cons:** Nothing works properly. Support is absolutely - top to bottom - terrible. Very expensive - literally 22.5 TIMES the cost of the software we tried to replace it with. Very difficult to move away from - their database structure is as well thought out as a dump truck full of spaghetti. Exporting our data is a nightmare. [Read All 189 Reviews](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) ## How should I be thinking about software pricing? [ Be an Informed Buyer: Understanding the True Cost of Business Software It's not just you-budgeting for business software is complicated. We're here to break it down. ](https://www.capterra.com/resources/business-software-cost/)