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Dear All, does somebody know whether is is possible to open the REPL with a pre-loaded script template ? It would be great to open the REPL and then be able to execute (interactive) script commands as if I were writing a script within my extension. At the minimum, I would need to open the REPL with some pre-loaded imports so that script objects and functions are recognized.

i would also find that useful.  but then a question is... how does the dependency management work there? with java.lang /stdlib it's a non-issue but what if you want to import custom apis, deal with versioning and transitive dependency etc 

My idea was to gather all dependencies (perhaps as an über-jar) as pass them beforehand as -cp parameters. Of course this means that all transitive dependencies must be known ahead of time.

Building on this last idea, if kotlinc had an "interactive" option (say -i) which could be combined with -script to that it executed the script and then stayed in the resulting REPL, we could do something like "kotlinc -cp {dependency jars} -i -script MyInitScript.kts", where the init script contains the import directives, declarations, etc. to configure the environment. That would be somewhat like having a poor man's scripting template.

that would be really wonderful. because a big limitation of REPLs for me is takes so much work to build up to the context needed.

Standard Kotlin REPLs (the `kotlinc` one and the IntelliJ counterpart) do not support custom script definitions yet. But you can build your own relatively easily.
The easiest way will be to use JSR-223 with `main-kts`, see the example here - <https://github.com/JetBrains/kotlin/blob/1.3.70/libraries/tools/kotlin-main-kts-test/test/org/jetbrains/kotlin/mainKts/test/mainKtsJsr223Test.kt#L39>
More advanced things are possible with the new REPL API which is introduced with 1.4 (starting from -M3, which is not published yet). Here you can have a look at the <https://github.com/Kotlin/kotlin-jupyter> for inspiration.
And if you'll run a REPL e.g. with `main-kts` definition, the preconfiguration mode you described is easily achievable with `@Import` annotation - you can configure things in a script and then simply `@Import` it into the REPL.