(Aron and Aron, Journal of Personality and Social Psychology 73:345–368, 1997) developed a personality construct of high sensitivity, characterized by a physiologically predetermined sensory processing sensitivity. Their unidimensional scale, the Highly Sensitive Person Scale (HSPS), measures the level of sensory processing sensitivity and can predict the negative emotional, social, behavioral outcomes such as social phobia, anxiety, depression, low self-efficacy, etc. However, previous research questioned the nature of the HSPS questionnaire, and proposed its division into two- or three-factor models. In a large body of studies SPS is seen as a trait that influences a life satisfaction of a person, but there is no clear evidence about the relationship of SPS with psychological well-being. Two studies (N = 860) extended previous findings in terms of the inner structure of sensory processing sensitivity and its connection with life outcomes. The objective of the study was to give the first evidence of the Highly Sensitive Person Scale's psychometric properties in a Russian-speaking population alongside the Aron and Aron scale and to describe the relations of sensitivity with the Psychological Well-being Scale (Riff, 1989). A sample of 860 respondents participated in the study: 350 undergraduate university student volunteers and 510 social media users (613 females and 247 males aged 15–43, M age = 20.8, SD age = 3.5). They filled out two questionnaires. Results did not confirm the initial linear model nor the three-factor solution. The hierarchical cluster and confirmatory analyses suggest that sensory processing sensitivity (SPS) can be described in a two-factor model consisting of ‘Ease of Excitation' and ‘Low Sensory Threshold' subscales. The t-test showed that only one subscale of Psychological well-being (personal growth) is disconnected with high sensitivity. Highly sensitive individuals are characterized by difficulties in relationships with others, limited number of interpersonal contacts, dependence on opinions and assessments of others, conformity, and low self-esteem therefore high sensitivity may be seen as a factor of psychological well-being decrease. Future studies should expand research on SPS as a sensitivity marker to both positive and negative outcomes, more research is needed that manipulates the positive or negative impact of SPS on life satisfaction and well-being and the study of dynamic changes in SPS in connection to psychological well-being. Lastly, the construct of sensitivity and views on its structure need further substantive concretization.