The @now/node@canary builder now supports Typescript. See this spectrum thread and this PR
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Currently, there is no clear pattern for deploying Node services written in Typescript via Now 2.0.
It appears the Zeit team is working on it:
But there is still no first class solution. The best approach for now seems to be to compile the TypeScript locally and push that up as a deployment (I'm verifying this on Spectrum).
This repo demos a working solution via npm run deploy.