This study addresses a controversial aspect of the change traditionally known as Middle English Open Syllable Lengthening (MEOSL): the variable results of lengthening in disyllabic (C)V.CVC stems, the heaven–haven conundrum. It presents a full philological survey of the recoverable monomorphemic input items and their reflexes in Present-day English (PDE). A re-examination of the empirical data reveals a previously unnoticed correlation between lengthening and the sonority of the medial consonant in forms such as paper, rocket, gannet and baron, as well as interplay between that consonant and the σ2 coda. The alignment of disyllabic stems with a medial alveolar stop and a sonorant weak syllable coda (Latin, better, otter) with (C)V.RVR stems (baron, felon, moral) opens up a new perspective on the reconstruction of tapping in English. The results of lengthening in disyllabic forms, including those previously thought of as ‘exceptions’ to the change, are modeled in Classical OT and Maxent OT, prompting an account which reframes MEOSL as a stem-level compensatory process (MECL) for all inputs. We show that OT grammars with conventional constraints can correctly predict variation in the (C)V.TəR stems and categorical lengthening or non-lengthening in other disyllabic stems. Broadening the phonological factors beyond the open-syllable condition for potential stressed σ1 inputs in (C)V.CV(C) stems allows us to apply the same constraints to stems whose input structure does not involve an open syllable and to propose a uniform account of stressed vowel quantity in all late Middle English mono- and di-syllabic stems.