Guided by Conditions of Learning Theory, this study investigated how internal and external factors related to web-based learning competence and whether age moderated such associations. Older adults from senior universities and community colleges in Shanghai were recruited (n = 1,310) in 2017. Web-based learning competence, internal factors (internet confidence, worry, and recognition), and external factors (internet environment and external support) were measured using scales with high reliability and validity. Hierarchical linear regressions with seven models were conducted using SPSS. The results showed that internal factors of internet confidence and worry as well as external factors of internet environment were significantly related to web-based learning competence. In addition, age moderated the influences of internet confidence, external support, and internet environment on learning competence. Community service providers should provide training and programs to improve web-based learning competence of older adults while considering age differences.