Aspects of the technology described herein improve a computing device's ability to accurately extract contextual features related to vehicle performance, vehicle usage, maintenance, recalls, and use the information to provide maintenance recommendations. Aspects of the technology described herein can analyze vehicle data from multiple sources including vehicle sensors, driver computing devices, maintenance records, used oil analysis, aftermarket sensors, and other data sources to ascertain a vehicle's operational state and detect warning signs that are statistically correlated with a mechanical failure or unsafe driving condition. When a warning sign is detected, the technology described herein can make maintenance suggestions to decrease the vehicle's failure probability. The maintenance suggestions can be generated by analyzing data from historical vehicle data to identify actions that improved the operational state for the same vehicle and/or similar vehicles.