Using Canadian Census microdata, 1971–2021, we compare immigrant and native-born earnings across ten arrival cohorts by gender and age at arrival. For two recent cohorts, an earnings-based positioning measure combines industry mean annual earnings with full-time or part-time status; multinomial-logit average marginal effects are estimated. The study also maps 2021 industry employment shares to external digital-intensity and telework-feasibility classifications. We find entry earnings gaps and incomplete cohort convergence persist, especially among women and recent cohorts. Across the two positioning cohorts, immigrants are less likely than comparable native-born workers to hold full-time jobs in higher-earnings industries; gaps vary by source region and do not uniformly narrow. Education is associated with better positioning but does not eliminate gaps. Immigrant employment is more concentrated in many digitally intensive categories but less concentrated in several higher-earnings, high-telework-feasibility industries; digital intensity is not systematically related to immigrant employment shares.