With the internet fast-penetrating the Nigerian populace, e-commerce businesses have become commonplace, this has given rise to an increase in the number of Nigerians shopping online. However, there is a growing concern that most Nigerian e-shoppers prefer foreign to local online shops, resulting in an online fund-leak from the local economy. This work presents a comparative analysis of the usability of e-commerce websites in Nigeria, highlights the key findings viz: security and lack of trust. The findings were then related to why Nigerians prefer shopping from foreign rather than local e-commerce websites. We argued that for e-commerce to thrive; usability should be given prime consideration, security should be guaranteed and trust-building ethos is practiced. We conclude that despite the ‘pay on delivery’ mode applied by e-commerce websites to woo customers and gain trust, the insecurity posed by the prevalence of online fraud in Nigeria has created apprehension and distrust among Nigerians towards local e-commerce websites and is contributing to why Nigerians prefer to buy from foreign rather than local e-commerce websites.