RubyMine debugger connection to SketchUp mysteriously stops - possible fix

Developers Ruby API
1

A while ago my RubyMine 2025.2.1 suddenly just stopped connecting to SketchUp 2025 for debug sessions. RM would launch Sketchup but the connect attempt would timeout. My settings hadn’t changed, I was stumped. I’m on a Mac so I ran ‘lsof -aP | grep -e SketchUp -e rubymine’ in a terminal immediately after launching SU from RM before the timeout. It showed that the two would connect but the port to RM was some random port, not the expected one for debugging.

Possible fix:

I trashed the .idea.log and started a new session. The interesting part of the log looked like this:

2025-09-07 10:34:09,203 [  21466]   WARN - #org.rubyforge.debugcommons.RubyDebuggerProxy - Cannot add breakpoint to: RubyDebugTarget[baseDir: null, debuggedFile: null, port: 6162, remote: true, process: null, process alive: n/a]
org.rubyforge.debugcommons.RubyDebuggerException: Interruped during reading catchpoint set (timeout: 20)
	at org.rubyforge.debugcommons.ReadersSupport.poll(ReadersSupport.java:432)
	at org.rubyforge.debugcommons.ReadersSupport.readCatchpointSet(ReadersSupport.java:400)
	at org.rubyforge.debugcommons.RubyDebuggerProxy.addExceptionalBreakpoint(RubyDebuggerProxy.java:310)
	at org.rubyforge.debugcommons.RubyDebuggerProxy.addBreakpointImpl(RubyDebuggerProxy.java:290)
	at org.rubyforge.debugcommons.RubyDebuggerProxy.attachToRubyDebug(RubyDebuggerProxy.java:216)
	at org.rubyforge.debugcommons.RubyDebuggerProxy.attach(RubyDebuggerProxy.java:180)
	at org.jetbrains.plugins.ruby.ruby.debugger.impl.RubyDebugProcess.attachToProxy(RubyDebugProcess.java:268)
	at org.jetbrains.plugins.ruby.ruby.debugger.impl.RubyDebugProcess.lambda$startAttachingThread$1(RubyDebugProcess.java:235)
	at java.base/java.lang.Thread.run(Thread.java:1583)
Caused by: java.lang.InterruptedException
	at java.base/java.util.concurrent.locks.AbstractQueuedSynchronizer$ConditionObject.awaitNanos(AbstractQueuedSynchronizer.java:1770)
	at java.base/java.util.concurrent.LinkedBlockingQueue.poll(LinkedBlockingQueue.java:460)
	at org.rubyforge.debugcommons.ReadersSupport.pollGently(ReadersSupport.java:329)
	at org.rubyforge.debugcommons.ReadersSupport.poll(ReadersSupport.java:422)
	... 8 more
2025-09-07 10:34:14,094 [  26357]   INFO - #c.i.m.l.c.q.QuotaManager2Impl - New quota state is: Available(current=11376.758, maximum=1000000, until=2025-09-29T21:00:00Z)
```
This looked like an exception was being thrown with something about RubyDebuggerProxy.addBreakpointImpl. 
I deleted all my breakpoints in RM and it connected!

I had been doing some file renaming (git mv) and there may have been some breakpoints pointing to nowehere.
2

I do not see a release for SketchUp versions running Ruby 3.2:

UPDATE - OK it now appears that the 2024 Debugger release is mislabeled “with Ruby 2.2”.

It should read “with Ruby 3.2”.

Did you have to build it yourself ?

3

@DanRathbun

No, I didn’t build it, and I’m not sure how I got 3.2.2. It was a few months ago, maybe rmv?

I am having an issue with RubyMine not expanding data types in the Threads & Variable pane maybe I have a ruby versions out of sync. Thanks I’ll take a look.

so SU25 uses ruby 2.2?

EDIT:

I did download the latest sketchup-ruby-debugger-1.5.0.0.tar. In ‘ThirdParty/lib/Mac/Ruby.framework/Versions’ it does have a ‘3.2.2’ folder. I tried to build it in Xcode, but it fails on an ifdef in integral_wrapper.hpp:

Screenshot 2025-09-09 at 8.58.47 AM
Screenshot 2025-09-09 at 8.58.47 AM1920×465 78 KB

soooo down the rabbit hole. I don’t know what to do about this.

4

NO SketchUp 2025 comes with Ruby 3.2.2.

UPDATE

OK it now appears that the 2024 Debugger release is mislabeled “with Ruby 2.2”.

It should read “with Ruby 3.2”.

5

Another post in another Rubymine debugger issue indicates use a different port than 7000:

6

Yes, it is known that the debug api will crash or hang if you use port 7000 on Mac. You can use any other port that is not already claimed by some other app or daemon or reserved for system use. I use 7777.