The phenolic composition of wine is mostly determined by the accumulation of the phenolic compounds in the grapes, as well as their extraction into wine. To increase their concentration in grapes, yield reduction is usually performed by pruning, while to increase the extraction in wines, the maceration on skins is extended for longer periods of time. The present study focuses on the possibilities to apply both strategies to improve the polyphenol composition of organic red wines of Romanian variety ‘Fetească neagră’, which stands to benefit more from technological interventions than other varieties, which naturally accumulate higher phenol concentrations in the grapes. In the vineyard three experimental pruning variants were made, with 20, 28 and 36 buds/vine, while for wine, maceration was performed for either 8 or 16 days for each grape variant. The phenolic profiles of wines were determined by HPLC methods. The main anthocyanidins, such as malvidin, petunidin, delphinidin, peonidin and cyanidin, as well as the acylated and coumaroylated derivatives of malvidin and peonidin were quantitatively determined. Some other phenolic compounds, of various classes, such as gallic, p-benzoic, p-coumaric and ferulic acid, catechin, epicatechin, myricetin, quercetin and trans-resveratrol were also determined. The quality of the organic ‘Fetească neagră’ wines depended highly on the vintage, but yield reduction and the extension of skin maceration duration were especially beneficial in the less favourable year, when classical technologies lead to less accumulation of sugars, colour and other polyphenols. Concomitant application of both strategies led to the best results, irrespective of the year.