Words are processed more easily when they have canonical phonotactic shapes, i.e., shapes that are frequent both in the lexicon and in usage. We explore whether this cognitively grounded constraint or preference implies testable predictions about the implementation of sound change. Specifically, we hypothesise that words with canonical shapes favour, or ‘select for’, sound changes that (re-)produce words with the same shapes. To test this, we investigate a Middle English sound change known as Open Syllable Lengthening (OSL). OSL lengthened vowels in disyllables such as ME /ma.kə/ make, but more or less only when they became monosyllabic and when their vowels were non-high. We predict that word shapes produced by this implementation pattern should correspond to the shapes that were most common among morphologically simple monosyllables and disyllables at the time when OSL occurred. We test this prediction against Early Middle English corpus data. Our results largely confirm our prediction: monosyllables produced by OSL indeed conformed to the shapes that were most frequent among already existing monosyllables. At the same time, the failure of OSL to affect disyllables (such as body) prevented them from assuming shapes that were far more typical of morphologically complex word forms than of simple ones. This suggests that the actuation and implementation of sound changes may be even more sensitive to lexical probabilities than hitherto suspected. Also, it demonstrates how diachronic data can be used to test hypotheses about constraints on word recognition and processing.