Amidst a high and increasing level of ambiguity, the quality of strategic management when ensuring the achievement by an enterprise of a sustainable development trajectory becomes particularly important. The issues of formation and efficient implementation of the strategic management mechanism bring into focus the task of finding tools for assessing the quality of strategic management. Meanwhile, the agenda of developing the tools to assess the quality of strategic management of an enterprise from the standpoint of achieving a sustainable development trajectory under ambiguity remains poorly understood. In this regard, the purpose of this study is to improve the quality of strategic management of industrial enterprises operating under uncertainty by developing and testing on the example of individual enterprises of the Donetsk region a toolkit for assessing the quality of strategic management in the context of an enterprise achieving a sustainable development trajectory. To reach this goal, this study uses a synthesis of systemic, cybernetic and synergetic approaches. For this purpose, within the framework of the study, a conceptualization of the main notions was carried out and theoretical and methodological approaches to the interpretation of the notions of “strategic management,” “sustainable development” and “strategic uncertainty” were proposed. Based on the author’s approaches to the interpretation of the main notions, it was suggested to assess the quality of strategic management in terms of the goal of such management, which is to achieve a sustainable development trajectory. Using the author’s approach, an assessment was made of the quality of strategic management of industrial enterprises in the Donetsk region in the context of their achievement of sustainable development. Approbation of the proposed tools led to the conclusion that the integral assessment indicator for all analyzed enterprises did not have an unambiguous and unidirectional downward trend. The foregoing indicates the absence of a stable trend towards the attractor for the analyzed period for all the enterprises in question, which makes highly topical the search for reserves to increase the efficiency of strategic management of industrial enterprises in the Donetsk region, which constitute the prospect for further research.