In this paper, the risk of the preparation of artificial DNAs via an interrupted automated solid-phase triester procedure is discussed. These results differ completely from the corresponding results obtained by a gradual non-automated synthesis, indicated as solution-phase chemistry. With experimental results focused on model systems under various conditions and molecular-mechanics calculations, it feels as a challenge to offer an explanation for this different behavior. Attention is briefly given to click-linked DNA fragments as a substitute of phosphate linkages.