The management of pregnancy in individuals with rheumatic disease requires the fine-tuned alignment of three dynamic factors: (i) the physiological immune reprogramming of gestation, (ii) fluctuations in disease activity, and (iii) the safety profiles of treatments for both mother and fetus. In normal pregnancy, immune tolerance is reinforced through mechanisms such as a shift toward Th2-skewed cytokine signaling, expansion of regulatory T cells, and trophoblast-mediated immunomodulation at the maternal–fetal interface. These adaptations not only facilitate fetal tolerance but can also mitigate activity in some autoimmune conditions while triggering flares in others. This chapter distills contemporary concepts in reproductive immunology and integrates them with practical, disease-specific recommendations for rheumatoid arthritis (RA), systemic lupus erythematosus (SLE), and spondyloarthritis (SpA). It emphasizes preconception counseling, trimester-specific monitoring, and risk reduction; it also briefly summarizes drug classes with acceptable safety profiles during pregnancy and lactation—framed by the 2024 EULAR updates. The strategic framework is straightforward: time conception to a period of sustained clinical quiescence, continue pregnancy-compatible disease-modifying therapy when needed, and coordinate interdisciplinary care to harmonize maternal health with fetal well-being.