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Re:Launch HN: EasyEmail (YC W18) – Gmail plug-in that helps ... by BjoernKW on Tuesday March 13, 2018 @01:55PM (#16578154)
Have you read Avogadro Corp (http://avogadrocorp.com/ )? That novel is based on the premise of a tool that is intended to help you write well-crafted emails yet quickly gets out of hand.

I'm not suggesting at all this will be the case here but this seems related and might be an interesting read.

Re:Launch HN: EasyEmail (YC W18) – Gmail plug-in that helps ... by stevenAthompson on Tuesday March 13, 2018 @02:07PM (#16578265)
That was my first thought as well.

My second thought was the Cory Doctorow story which predicted that the first true AI will be the result of a machine learning spambot and a machine learning antispam bot getting stuck in an arms race.

This tech would make for an excellent means for spammers and malware authors to bypass spam filters easily.

1)Infect user. 2)Generate new content based on old emails. 3)Infect everyone. 4)Repeat.

Re:Launch HN: EasyEmail (YC W18) – Gmail plug-in that helps ... by bluesign on Tuesday March 13, 2018 @04:04PM (#16579283)
Or more simpler:

Use same content, change attachment

Sadly I came across this before

Re:Launch HN: EasyEmail (YC W18) – Gmail plug-in that helps ... by filipt on Tuesday March 13, 2018 @02:12PM (#16578330)
Oh man hahah, that's gotten dark real quick! Promise we're not trying to do that
Re:Launch HN: EasyEmail (YC W18) – Gmail plug-in that helps ... by filipt on Tuesday March 13, 2018 @02:00PM (#16578205)
Never read it, but I just looked it up and will order it soon. Gotta make sure we don't make the same mistakes ;) Definitely not something we're going after, haha!