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Hello David,

sorry for the delay. It's possible in case of JavaScript debug sessions:

https://www.jetbrains.com/help/ruby/2016.1/live-editing-of-html-css-and-javascript.html

As for Ruby we have a corresponding request and will investigate the possibility of its implementation. Please vote for it:

https://youtrack.jetbrains.com/issue/RUBY-12592

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