Financial freedom is one of the goals economies dream to achieve in both developed and developing nations through taxation. However, non-compliance according to previous literature hindered tax authorities from achieving the set tax collection targets. Drop in National Residential rental income tax collection was reported in the year 2020 by Organization for Economic Cooperation and Development in Kenya. Similarly, the Country’s tax authority data revealed reduction in tax collection for Kasarani Sub County in the year 2020/2021. The key objective of this research was to investigate influence that tax collection strategies have on the compliance of residential rental income earners in Kasarani sub-county in Kenya. The specific objectives aimed at determining the influence of taxpayers trust building, Knowledge & tax awareness, modern technology adoption and effective tax law enforcement strategies on the compliance of residential property owners. The research was anchored on the social exchange, reasoned action, technology acceptance and economic deterrence theories. Descriptive research design was applied to evaluate the influence of independent variables on the dependent ones. A population of 871 property owners was considered with 274 respondents obtained from population target in aid of stratified sample model whereas questionnaires were applied in collecting primary data. Analysis of data was run on multiple regression model supported with descriptive techniques. Validity test together with reliability analysis was done using Analysis of Variance and Cronbach Alpha models. Multicollinearity, normality, heteroscedasticity, and linearity tests were undertaken for diagnostic purpose. Study findings indicated that tax payer’s trust building (t=3.399, p<0.05), knowledge & awareness campaign (t=5.732, p<0.05), modern technology (t=2.897, p<0.05) and effective tax law enforcement strategy (t=4.795, p<0.05) had positive and significant effect on the compliance of Residential Rental Income earners in Kasarani Sub County. The study concluded that mutual trust building aided mobilization of public support for tax collection agenda prompting the initially skeptic residential rental income taxpayers to embrace tax compliance, that tax knowledge & awareness strategy positively affected tax compliance, tax collection and reporting through the modern technology based systems proved to significantly support tax compliance and that the tax law enforcement measure is very strategic in influencing tax income collection. Study recommended use of competitive communication skills as a trust building window in formal and informal interactions between the taxpayer and agency on matters tax compliance. The study recommended the training of taxpayers on use of technology and expansion of its tax labs centers networks close at the Sub County level for easy access.