Self-supervised learning (SSL) has transformed representation learning for large models, yet remains unexplored for microcontroller (MCU)-class models with fewer than 500K parameters. We identify three obstacles at this scale -- projection head dominance, representation bottleneck, and augmentation sensitivity -- and propose Capacity-Aware Distilled Self-Supervised Learning (CA-DSSL), a teacher-guided framework that overcomes them without labels or text supervision. CA-DSSL combines asymmetric distillation from a frozen DINO ViT-S/16 teacher, multi-scale feature distillation for spatial representations, and a progressive augmentation curriculum. On a MobileNetV2-0.35 backbone (396K parameters) pretrained on CIFAR-100, CA-DSSL reaches 62.7 0.5% linear-probe accuracy (3-seed mean) -- surpassing SimCLR-Tiny by 18 pp, matching SEED (61.7%) with 10 fewer projection parameters (426K vs. 3.15M), and reaching 94.0% of a supervised upper bound. Standard SSL methods (BYOL-Tiny, DINO-Tiny) collapse entirely at this scale. On Pascal VOC detection, CA-DSSL achieves 2.3 the mAP of random initialization and +3 pp over SEED, though SimCLR-Tiny matches CA-DSSL on detection mAP. The deployed backbone occupies 378 KB (INT8) with no inference overhead from pretraining. Preliminary ImageNet-100 experiments reveal that CA-DSSL's advantage is specific to small-data regimes; scaling to ImageNet-1K is discussed as future work.