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From earlier winberry, apparently a variant of wineberry (Middle Englishwinberie) with regular shortening of the first vowel before a consonant cluster; in wineberry, this was prevented or reversed due to analogy.
The assimilation of /nb/ to /mb/ seen in some forms is to be expected (compare hemp < Old English henep). Other forms show the influence of unrelated words; the consonantism of forms with initial wh- is probably due to the influence of whin, while windberry clearly represents remodelling as wind + berry.
1871, C. S. Gregson, “Varieties and Aberrations of Lepidoptera”, in Edward Newman, editor, The Entomologist, volume V, London: Simpkin, Marshall, & Co., page 75:
Another variable species: when fed upon whimberry or cowberry it is a most distinct-looking insect, often with the white patches placed in a triangle, one on the disk, one on the hind margin, and the usual one: no band.
1900, Helen Brierley, Morgan Brierley, a Memoir: With a Selection from His Writings, Rochdale: James Clegg, page 260:
The lovely pink bloom of the whimberry stalk drops on the turf as the inner part knits itself into hard, green, beady fruit, whilst the leafage changes from a soft green to yellowish brown.
2011 December 30, Nina Bawden, In My Own Time: Almost an Autobiography, Little, Brown Book Group, →ISBN, page 38:
She made whimberry tarts and we ate them with thick, yellow cream until we were tight as drums.