The research in this paper focuses on presenting the complexity of the English progressive verb form. Its basic aim is to investigate the contextual conditions under which the progressive form, as context dependent and stylistically marked, may realise its various levels of meaning. We primarily rely on Leech’s theory (2004) of the English progressive, revisiting the author’s arguments on the semantic layering of this form, such as duration, limited duration, and completeness/incompleteness of verb situations. We will refer to these levels of meaning as aspectual and temporal but will also try to shed light on some other implications of the progressive form in sentential context, such as future time reference, habituality, intention, subjectivity, and emotional colouring. We premise that the temporal meaning of the progressive verb form is derived with reference to what is seen as the contextually independent, or simple, verb form, which occurs in the lexical material surrounding the progressive form itself. We further emphasise that the reference to simple verb forms may contribute to comprehending the levels of the aspectual and temporal meaning of the progressive, but that some other semantic values, such as those mentioned above, may allow for certain pragmatic interpretations and stylistic implications under the direct influence of a particular sentential context. Consequently, this occurs along with the increased use of the progressive in contemporary English, even for situations regularly expressed in simple verb form. Finally, we summarise various contextual factors influencing the proper interpretation and use of this semantically versatile English grammatical item and highlight the situations where the progressive might be interchangeable with the simple verb form.