Understanding why some species succeed in naturalizing and invading ecosystems, while others do not, has intrigued scientists since Darwin’s time. The Pre-Adaptation Hypothesis posits that introduced species closely related to natives, and thus ecologically similar, are more likely to establish. This concept aligns with the Climate Matching Hypothesis, which emphasizes environmental similarity between native and invaded regions as a key factor in invasion success. However, conflicting evidence leaves the role of biogeographic origin and climatic affinity in predicting invasion risk unresolved. Here, we examine how biogeographical origin, climatic matching, and inter- and intraspecific pre-adaptation influence the success of congeneric plant species introduced to the Canary Islands, an oceanic archipelago with Mediterranean climatic affinities. We integrated phylogenetic, climatic and occurrence data at two levels: (i) interspecific comparisons of phylogenetic distances and climatic similarity between each introduced species and its closest native counterpart; and (ii) intraspecific analysis of climatic niche dynamics between native and introduced ranges. Most introduced congeneric species originate from the Mediterranean Basin and temperate Europe, with a notable contribution from the Neotropics. While Mediterranean and temperate European introduced taxa were phylogenetically closer to native Canarian species, we found no consistent evidence of pre-adaptation when climatic similarity among congeneric species pairs was also considered. In contrast, intraspecific analyses revealed widespread niche expansion, regardless of origin. However, species from the Mediterranean and Neotropical origin displayed a greater effect on climatic niche stability, suggesting stronger climatic matching. Overall, our findings highlight the prevalence of niche shifts among introduced plant species and underscore the role of climatic niche expansion in facilitating biological invasions. These results have key implications for assessing invasion risks in increasingly disturbed insular regions worldwide.