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From what I can tell terser is built around an older version of the rollup API which uses transformBundle to transform the code. In rollup >=0.60 this has been renamed to transformChunk[1][2] which is the one conditional 2.x is hooking up to so this explains why terser isn't being run.
The odd thing is that the rollup CLI still sees transformBundle as a valid hook.
My suggestion is that you downgrade to v1.1 (npm i rollup-plugin-conditional@1.1 --save-dev) for now while I continue the investigation.
Am I misusing the api? Expected behavior is if the conditional is true the bundle gets minified...
My rollup config looks like this:
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