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Changes leading up to Middle and Modern English
For a detailed description of the changes between Old English and Middle/Modern English, see the article on the phonological history of English. A summary of the main vowel changes is presented below. Note that the spelling of Modern English largely reflects Middle English pronunciation. Note also that this table presents only the general developments. Many exceptional outcomes occurred in particular environments, e.g. vowels were often lengthened in late Old English before ; vowels changed in complex ways before, throughout the history of English; vowels were diphthongized in Middle English before ; new diphthongs arose in Middle English by the combination of vowels with Old English w, g > , and ġ ; etc. The only conditional development considered in detail below is Middle English open-syllable lengthening. Note that, in the column on modern spelling, CV means a sequence of a single consonant followed by a vowel.

Note that the Modern English vowel usually spelled au (British, American ) does not appear in the above chart. Its main source is late Middle English /au/, which come from various sources: Old English aw and ag ("claw" < clawu, "law" < lagu); diphthongization before ("sought" < sōhte, "taught" < tāhte, "daughter" < dohtor); borrowings from Latin and French ("fawn" < Old French faune, "Paul" < Latin Paulus). Other sources are Early Modern English lengthening of before  ("salt, all"); occasional shortening and later re-lengthening of Middle English  ("broad" <  < brād); and in American English, lengthening of short o before unvoiced fricatives and voiced velars ("dog, long, off, cross, moth", all with  in American English, at least in dialects that still maintain the difference between  and ).

As mentioned above, Modern English is derived from the Middle English of London, which is derived largely from Anglian Old English, with some admixture of West Saxon and Kentish. One of the most noticeable differences among the dialects is the handling of original Old English. By the time of the written Old English documents, the Old English of Kent had already unrounded to, and the late Old English of Anglia unrounded  to. In the West Saxon area, remained as such well into Middle English times, and was written u in Middle English documents from this area. Some words with this sound were borrowed into London Middle English, where the unfamiliar was substituted with. Hence: Note that some apparent instances of modern e for Old English y are actually regular developments, particularly where the y is a development of earlier (West Saxon) ie from i-mutation of ea, as the normal i-mutation of ea in Anglian is e; for example, "stern" < styrne < *starnijaz, "steel" < stȳle < *stahliją (cf. Old Saxon stehli). Also, some apparent instances of modern u for Old English y may actually be due to the influence of a related form with unmutated u, e.g. "sundry" < syndriġ, influenced by sundor "apart, differently" (cf. "to sunder" and "asunder").
 * "gild" < gyldan, "did" < dyde, "sin" < synn, "mind" < mynd, "dizzy" < dysiġ "foolish", "lift" < lyft "air", etc. show the normal (Anglian) development.
 * "much" < myċel shows the West Saxon development.
 * "merry" < myriġ shows the Kentish development.
 * "build" < byldan and "busy" < bysiġ have their spelling from West Saxon but pronunciation from Anglian.
 * "bury" < byrġan has its spelling from West Saxon but its pronunciation from Kentish.