diff --git a/.circleci/config.yml b/.circleci/config.yml
index 42171ddb58d..a0cf69d94b4 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -40,6 +40,7 @@ test_containers:
     DD_AGENT_HOST: testagent
     DD_TRACE_AGENT_PORT: 9126
     DATADOG_GEM_CI: true
+    RUBYOPT: -r/app/patch_log_device
   - &container_parameters_environment
     - *container_base_environment
     - TEST_DATADOG_INTEGRATION: 1
diff --git a/.github/PULL_REQUEST_TEMPLATE.md b/.github/PULL_REQUEST_TEMPLATE.md
index 592b554b98f..1e2e6c0a667 100644
--- a/.github/PULL_REQUEST_TEMPLATE.md
+++ b/.github/PULL_REQUEST_TEMPLATE.md
@@ -5,17 +5,6 @@ for guidance on how to set up your development environment,
 run the test suite, write new integrations, and more.
 -->
 
-**2.0 Upgrade Guide notes**
-<!--
-(If this PR is for 1.x, please delete this section)
-If this PR introduces a breaking change, update the
-https://github.com/DataDog/dd-trace-rb/blob/2.0/docs/UpgradeGuide2.md
-in this PR with either:
-* A migration path for this change. In other words, how to continue using their application without behavior changes
-in 2.0 (e.g. environment variable 'X' renamed to 'Y').
-* That there's no alternative; we removed support for this feature.
--->
-
 **What does this PR do?**
 <!-- A brief description of the change being made with this pull request. -->
 
diff --git a/patch_log_device.rb b/patch_log_device.rb
new file mode 100644
index 00000000000..f08b44e9a4c
--- /dev/null
+++ b/patch_log_device.rb
@@ -0,0 +1,16 @@
+if RUBY_ENGINE == 'jruby'
+  require 'logger'
+  ::Logger::LogDevice.prepend(
+    Module.new do
+      def write(message)
+        $stdout.puts("[Writing] ProcessID: #{Process.pid}, ThreadID: #{Thread.current.object_id}, Message: #{message}")
+        super(message)
+      end
+
+      def close
+        $stdout.puts("[Closing] ProcessID: #{Process.pid}, ThreadID: #{Thread.current.object_id}")
+        super
+      end
+    end
+  )
+end
diff --git a/spec/datadog/core/environment/execution_spec.rb b/spec/datadog/core/environment/execution_spec.rb
index 19699850c27..e7794bcf7c9 100644
--- a/spec/datadog/core/environment/execution_spec.rb
+++ b/spec/datadog/core/environment/execution_spec.rb
@@ -72,7 +72,7 @@
             f.close
 
             out, = Open3.capture2e('pry', '-f', '--noprompt', f.path)
-            expect(out).to eq('ACTUAL:true')
+            expect(out).to be_end_with('ACTUAL:true')
           end
         end
       end
@@ -275,7 +275,7 @@ def test_it_does_something_useful
         end
 
         expect(err).to be_empty
-        expect(out).to eq('true')
+        expect(out).to be_end_with('true')
       end
     end
   end