The present paper deals with synchronic and diachronic problems of the category of the so-called Ionic iteratives (e.g. Hom. φεύγεσκον, ἵστακε). Following a general overview of their morphological and semantic peculiarities, at first those Homeric iteratives are examined that show irregular derivational morphology. Then a new synchronic segmentation of the iteratives is proposed, according to which the units -σκον, -σκε, etc. are to be regarded as complex verbal endings. In the second half of the paper, after a survey of previous theories on the question, the origin and development of the iteratives are described and, in connection with this, a morphologically based explanation for their augmentlessness is offered.