Message is not clear: "Unable to start debug session: Failed to detect dbgshim directory."
Answered
Similar to this post: https://rider-support.jetbrains.com/hc/en-us/community/posts/360005064860-Unable-to-start-debug-session-Failed-to-detect-dbgshim-directory-?flash_digest=148ef3ff023324e6783459f4232b204fa9250b4c
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I've replaced
ENTRYPOINT ["dotnet","WebApplication23.dll"]
with
ENTRYPOINT ["dotnet","watch","WebApplication23.dll"]
in my dockerfile, and now rider console outputs this message: "Unable to start debug session: Failed to detect dbgshim directory."
It's not clear how to deal with this message

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Hello Eugeniy,
Could you please enable Debug Trace scenario (Help | Trace scenarios), reproduce the issue, collect the logs as well as dockerfile and submit a request with this information to our bug tracker for further investigation. Disable Trace Scenario after. Thank you in advance!
Just for the record, this error was occurring for me.
I was compiling my solution targeting netcoreapp2.2 using .net sdk 2.2
After installing .net core sdk 3, this Rider debugging error started occurring on for me.
I create a global.json pointing to 2.2 sdk (dotnet new globaljson --sdk-version 2.2.402) and debugging started working again.
Hello, thank you for sharing the details. We indeed have encountered some issue with .NET Core 3, like: RIDER-34634 and RIDER-33356. If it is similar to yours, then please watch for monitoring the status or let me know if it differs.