As the most widely used manufactured material on Earth, concrete poses serious societal and environmental concerns which call for innovative strategies to develop greener concrete with improved strength and toughness, properties that are exclusive in man-made materials. Herein, we focus on calcium silicate hydrate (C-S-H), the major binding phase of all Portland cement concretes, and study how engineering its nanovoids and portlandite particle inclusions can impart a balance of strength, toughness and stiffness. By performing an extensive +600 molecular dynamics simulations coupled with statistical analysis tools, our results provide new evidence of ductile fracture mechanisms in C-S-Hreminiscent of crystalline alloys and ductile metalsdecoding the interplay between the crack growth, nanovoid/particle inclusions, and stoichiometry, which dictates the crystalline versus amorphous nature of the underlying matrix. We found that introduction of voids and portlandite particles can significantly increase toughness and ductility, specially in C-S-H with more amorphous matrices, mainly owing to competing mechanisms of crack deflection, voids coalescence, internal necking, accommodation, and geometry alteration of individual voids/particles, which together regulate toughness versus strength. Furthermore, utilizing a comprehensive global sensitivity analysis on random