Purpose: The study of challenges encountered by the workers belonging to the unorganized sector leads to have greater understanding in order to provide awareness among the workers possessed with un-skilled, semi-skilled, and high-skilled. Present workers in the unorganized sectors are not protected and monitored by the government due to that more job-related exploitation and violations are faced by the workers. This is considered essential to provide tailored content for workers belonging to different categories such as Minor ranchers, landless rural laborers, and tenant farmers. The study is done with the intention of identifying challenges faced by these three groups of workers. Design/Methodology/ Approach This was conducted by using an exploratory research design on a sample size of 414 comprising 138 respondents from three categories of workers belonging to unorganized sector selected, namely Minor ranchers, landless rural laborers, and tenant farmers. The study used a convenience sampling technique; the data was collected with the help of a formal interview schedule. Likert scale statements were used to record the responses ranging from highly agree to highly disagree and multiple discriminant analysis was applied for data processing. Findings The study found that Minor Ranchers workers are not getting reasonable wages and advances, and Ransome is paid to middlemen by the land ranchers, and wages are paid on time to them. The Landless rural laborers are not receiving wages on time and insufficiency in getting workers at the time of harvesting created more work burden. Tenant farmers need to pay for the length of working hours and for overtime. Originality Although studies on complexities and challenges faced by unorganized sector workers are available, studies on the specific category of workers of the unorganized sector are found to be rare. This research finding will provide sufficient insight to the researchers and academicians as well as to the workers belonging to the different groups with educational backgrounds.