Cautious Hero - Shinchou Yuusha - Kono Yuusha ga Ore Tueee Kuse ni Shinchou sugiru - The Hero is Overpowered but Overly Cautious - Shincho Yusha - The Hero is Invincible but Too Cautious
Season 2 When?!
Anime
It is needed in our lives and hearts
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Very unlikely. The problem is that the novel is pretty much on a hiatus (read: axed) before it got finished. There's like no reason adapting something that has died, at least I never seen something like that ever happened. Even more for a series that ain't exactly super popular like this one.
You might say that alot of animes recently got some unlikely sequels such as KnT, Hataraku Maou, and Masamune for example. Sorry to burst your bubble, but the thing these 3 got in common is that the source is finished. And even in Masamune case, it's clearly meant to promote the author next manga which is a sequel to it.
Also, Cautious Hero author are busy writing something else instead of continuing this one. So, until the day the author decided to pick this one up again, the chance is pretty much 0.
It's a shame though. Because the next arc after the anime is the peak of the novel so far.
Well it would be cool if they at least animated the next big arc
Novel recently confirmed return on twitter.
They've never announced a 2nd season but there's always hope. The Devil is a Part-Timer got a 2nd season like 9 years later so it's not impossible. Though I'd prefer sooner rather then later. Have you listened to the Drama CD?
Drama CD where? WHERE????