Orthodox Jewish apostasy blogging of the 21st century was a reform-minded, medial phenomenon that was part of the new media challenge to rabbinic authority culminating in the so-called “Internet asifa” of 2012, a large demonstration of anti-Internet rabbis and their followers in Citi Field in Queens, NY. But apostasy blogs, such as Unpious.com, also chronicled an identity transformation for those bloggers who first staged their apostasy virtually and later, in real life. I argue that Jewish doubt blogging, which took place largely anonymously, had its roots in maskilic (Jewish enlightenment) autobiography in Germany and Eastern Europe of the 19th century. In my analysis, I compare the fate of Jewish apostasy bloggers with that of the likewise anonymous, maskilic autobiographers of the past and show how both movements were composed of traditionally-educated, secularizing Jews who used personal narrative to create a literature of subversion that overturned the accepted norms of Orthodox communities.