I went through the entire app and two Google pages and didn't found it. How can I enable the output window?
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If you are referring to build output: As of the latest EAP, you can enable this via:
Preferences -> Build, Execution, Deployment -> Toolset and Build -> Write log to output
It is disabled by default as of the time of this writing.

marknuzz
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Currently the build output window available only for not incremental build. We try to add it in next EAP build.

Mikhail Filippov
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For anyone looking for the "Debug window", it's on View->Tools Windows->Debug and change the mode to "Debugger Output (LLDB)" https://www.jetbrains.com/help/rider/Debug_Tool_Window.html