The current paper has presented the study results (2015–2020) of the influence of changing weather conditions on durum winter wheat productivity and grain quality. The purpose of the study was to identify the main stress factors limiting durum winter wheat productivity under changing climate conditions and to determine the direction and issues for further breeding. The objects of the study were the varieties ‘Amazonka’, ‘Agat Donskoy’, ‘Kristella’, ‘Lazurit’, ‘Oniks’, ‘Diona’, ‘Eyrena’, ‘Yakhont’, ‘Kiprida’, ‘Yubilyarka’, ‘Yantarina’, ‘Uslada’, ‘Donchanka’ (a standard variety) developed by the FSBSI Agricultural Research Center “Donskoy”. There have been studied the meteorological data (average daily temperatures and precipitation) through the years of study as well. On the basis of the analysis, there have been established main stress factors of these years that affected productivity, namely drought in different vegetation periods with the pre-sowing and sowing periods in August and September of 2019; the periods ‘sprouts-tillering’ in October, December and the periods ‘tillering-stem extension’ in March, April; grain filling period in 2020; atmospheric drought during the period of active vegetation in April, June of 2018; excessive moisture with rainfalls and squally winds that caused lodging, diseases, grain flowing off and discoloration in 2014–2015, 2015–2016. The agricultural year 2016–2017 was the most favorable in terms of temperature regime, precipitation and their distribution (at the level of the long-term average), with an average varietal productivity of 9.49 t/ha. Yield decrease depending on this or that stress factor (in comparison with the favorable year of 2017) was on 54.5% in 2019, 32.5% in 2020 and on 21.4 in 2015 and 27.2% in 2016. The exception was the year of 2018, when with sufficient soil moisture, productivity was on 26.3% more than in 2017. Due to the study results of winter durum wheat varieties according to their traits and properties to the indicated stress factors in 2015–2020, there have been identified the issues for each direction, the solution of which will be aimed at developing stress-resistant, resistant to lodging and diseases varieties with large stable yields and high grain quality.