Scaling educational assessment with large language models requires not just accuracy, but the ability to recognize when predictions are trustworthy. Instruction-tuned models tend to be overconfident, and their reliability deteriorates as curricula evolve, making fully autonomous deployment unsafe in high-stakes settings. We introduce CHiL(L)Grader, the first automated grading framework that incorporates calibrated confidence estimation into a human-in-the-loop workflow. Using post-hoc temperature scaling, confidence-based selective prediction, and continual learning, CHiL(L)Grader automates only high-confidence predictions while routing uncertain cases to human graders, and adapts to evolving rubrics and unseen questions. Across three short-answer grading datasets, CHiL(L)Grader automatically scores 35-65% of responses at expert-level quality (QWK >= 0.80). A QWK gap of 0.347 between accepted and rejected predictions confirms the effectiveness of the confidence-based routing. Each correction cycle strengthens the model's grading capability as it learns from teacher feedback. These results show that uncertainty quantification is key for reliable AI-assisted grading.