Still very vague. Your friend would have to have gotten authorisation to board his flight on exception of either to unite with an immediate/extended family member in Canada as a citizen/PR/TR or any other valid reason he must have declared to the airline before jumping on a plane.Well, that was his first landing as a PR as he got approved in October.
Read more here - https://www.canada.ca/en/immigration-refugees-citizenship/services/coronavirus-covid19/travel-restrictions-exemptions.html#extended-citizen-pr
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