The purpose of this study is to shed more light on the transesterification processes in alcohol‐initiated and tin(II) 2‐ethylhexanoate (SnOct2)‐catalyzed polymerizations of lactides at low or moderate temperatures. Ethanol‐initiated polymerizations are conducted in concentrated solutions at 80 °C and a strong dependence of even/odd equilibration on the alcohol/Sn ratio. Around or above 120 °C cyclization of poly(l‐lactide) via “backbiting” occurs as a third mechanism. However, poly(m‐lactide) shows a higher cyclization tendency and yields cyclics even at 100 °C. Combinations of ethanol and certain cyclic dibutyltin(IV) catalysts also yield cyclic oligomers of l‐lactide at 80 °C. Reaction conditions allowing for a total suppression of all transesterification reactions are not found, but even‐numbered poly(m‐lactide)s with a purity >95% are obtained at 70 or 60 °C.