Native ads are ubiquitous in the North American digital news context. Their form, content and presentational style are practically indistinguishable from regular news editorials, and thus are often mistaken for informative content by newsreaders. This advertising practice is deceptive, in that it exploits loopholes in human digital literacy. Despite this, it is flourishing as a lucrative digital news advertising format. This paper documents and compares the 2018 Canadian news editorial writing

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... nd advertising practices in an effort to highlight their similarities and differences for potential automatic detection and categorization. We collected 10 native ads and 10 editorial pieces from 4 Canadian newspapers. The 80 analyzed articles consisted of 40 native ads contentmatched to editorials in the same newspaper. The individually-matched pairs and overall practices in the 2 groups were content-analyzed and compared. Native ads did not differ much from editorial articles in content but were likely to be surrounded by different types of advertising. In addition, advertisement labelling practices were inconsistent across national papers. We call for increased efforts in regulation and automatic detection of convert advertising by a more nuanced categorization and their more explicit labeling in the digital news.