The focus of this work was to find appropriate methods for the generation of highly silylated ferrocenes to investigate the effects of steric overload and charge stabilization by the silyl groups. Reactions were carried out by metalation of bromoferrocenes FeC10Br10 and FeC10Br8Me2 followed by quenching with DMSCl. We observed that the introduction of silyl groups inhibits further silylation yielding only a mixture of polysilylated compounds FeC10DMSnH10-n (n = 10, 9, 8) containing the targeted decasilylated ferrocene in low yields. The reactivity of the polymetalated intermediates as well as the selectivity of the products is drastically improved when electron donating groups were applied as the corresponding octasilylated metallocenes FeC10DMS8Me2 were isolated purely in good yields despite the sterically demanding substituents.