Living cationic ring‐opening polymerizations of 2‐ethyl‐2‐oxazoline and purification of the resulting polymers were performed utilizing an automated synthesizer. Eight polymers (500 mg scale) as well as 40 polymers (150 mg scale) were synthesized in parallel to investigate the reproducibility and the living character of the polymerizations. The poly(2‐ethyl‐2‐oxazoline)s obtained such were characterized by means of 1H NMR spectroscopy, MALDI‐TOF mass spectrometry and online gel permeation chromatography.