Background: Rheumatoid arthritis (RA) is an autoimmune, chronic inflammatory disease of unknown etiology characterized by symmetric polyarthritis. It is the most common form of chronic inflammatory arthritis. It can also cause a variety of extra-articular manifestations, such as vasculitis, nodules, and accelerated atherosclerosis. RA affects 0.5–1% of the adult population worldwide. Females are more commonly affected than males, which can be attributed to the role of estrogen in enhancing immune response. Genetic and environmental factors play an important role in the pathogenesis of RA. Materials and Methods: This is a prospective study conducted in the Department of OBGY and Orthopaedics. Data about RA pregnancies were collected before conception and during each trimester and post- partum period. All the patients were prospectively followed at the multidisciplinary Pregnancy Clinic for Rheumatic Diseases. Data collection was performed at five time points: preconception visit (3–6 months before conception), during each trimester of pregnancy (first: 8–12 weeks of gestation, second: 18–24 weeks, third: 30–36 weeks), and up to 6 months after delivery. Results: Flare rates during pregnancy in patients with RA are associated with active disease in early pregnancy. A total of 65 pregnant patients were identified. No patient with RA experienced more than one episode of flare during pregnancy. Comparing patients with flares with those without them, the discontinuation of TNFi in early pregnancy correlated with the risk of flares. Conclusion: Elevated disease activity and TNFi discontinuation in early pregnancy may cause a relapse of disease activity in patients with RA. Restart of medication controls disease activity in pregnant patients with RA but shows insufficient effect in pregnant patients. The data indicate that tailored medication should be considered beyond conception to stabilize low disease activity and to prevent a flare during pregnancy.