Technologies for user-assisted machine learning includes a compute device configured to request user assistance to classify sensor data in response to a determination that a confidence score associated with the classification of the sensor data is below a threshold value and/or if the classification of the sensor data is unknown. In an illustrative embodiment, the compute device is configured to communicate with an activity monitor device, such as a smart pet collar, to determine activities of the subject (e.g., a pet) based on classification data received from the smart pet collar.