An improved machine learning system is provided. For example, a content management server may provide a digital assessment of a user's handwriting to assess the user's knowledge of a language. The assessment may comprise adaptive technology to help determine initial questions to provide to the user as well as follow-up questions to clarify appropriate remediation content in a particular context. The content management server may also provide real-time analysis, including assessing multiple users at the same time in adjusting the assessment based on the digital input from each of these users. In some examples, the content management server may incorporate handwriting analysis methods to perform object detection and score handwriting input.