A hydraulic system of a work machine includes a first hydraulic device to operate in a first operation mode while pressure of hydraulic oil supplied from a hydraulic pump via a first oil passage is equal to or higher than a first pressure threshold. The hydraulic oil in the first oil passage is to be discharged via a second oil passage. A pilot check valve is provided in the second oil passage and has a pilot port to receive a pilot pressure of the hydraulic oil. The pilot check valve is closed to stop discharging the hydraulic oil in the first oil passage through the second oil passage while the pilot pressure is lower than the fourth pressure threshold. The pilot check valve is opened while the pilot pressure is higher than or equal to the fourth pressure threshold. The first hydraulic device is a ride control device.