diff --git a/lib/datadog/di/code_tracker.rb b/lib/datadog/di/code_tracker.rb
index 5ace92a17d2..023f7ea4fdd 100644
--- a/lib/datadog/di/code_tracker.rb
+++ b/lib/datadog/di/code_tracker.rb
@@ -91,7 +91,7 @@ def start
             # before release.
             if component = DI.current_component # steep:ignore
               raise if component.settings.dynamic_instrumentation.internal.propagate_all_exceptions
-              component.logger.warn("Unhandled exception in script_compiled trace point: #{exc.class}: #{exc}")
+              component.logger.debug { "di: unhandled exception in script_compiled trace point: #{exc.class}: #{exc}" }
               component.telemetry&.report(exc, description: "Unhandled exception in script_compiled trace point")
               # TODO test this path
             else
diff --git a/lib/datadog/di/component.rb b/lib/datadog/di/component.rb
index 797449c077d..17c713c536f 100644
--- a/lib/datadog/di/component.rb
+++ b/lib/datadog/di/component.rb
@@ -20,7 +20,7 @@ def build(settings, agent_settings, logger, telemetry: nil)
           return unless settings.respond_to?(:dynamic_instrumentation) && settings.dynamic_instrumentation.enabled
 
           unless settings.respond_to?(:remote) && settings.remote.enabled
-            logger.debug("Dynamic Instrumentation could not be enabled because Remote Configuration Management is not available. To enable Remote Configuration, see https://docs.datadoghq.com/agent/remote_config")
+            logger.warn("di: dynamic instrumentation could not be enabled because Remote Configuration Management is not available. To enable Remote Configuration, see https://docs.datadoghq.com/agent/remote_config")
             return
           end
 
@@ -55,12 +55,16 @@ def environment_supported?(settings, logger)
           # TODO add tests?
           unless settings.dynamic_instrumentation.internal.development
             if Datadog::Core::Environment::Execution.development?
-              logger.debug("Not enabling dynamic instrumentation because we are in development environment")
+              logger.warn("di: development environment detected; not enabling dynamic instrumentation")
               return false
             end
           end
-          if RUBY_ENGINE != 'ruby' || RUBY_VERSION < '2.6'
-            logger.debug("Not enabling dynamic instrumentation because of unsupported Ruby version")
+          if RUBY_ENGINE != 'ruby'
+            logger.warn("di: cannot enable dynamic instrumentation: MRI is required, but running on #{RUBY_ENGINE}")
+            return false
+          end
+          if RUBY_VERSION < '2.6'
+            logger.warn("di: cannot enable dynamic instrumentation: Ruby 2.6+ is required, but running on #{RUBY_VERSION}")
             return false
           end
           true
diff --git a/lib/datadog/di/instrumenter.rb b/lib/datadog/di/instrumenter.rb
index 96df68465f8..05ff256bb80 100644
--- a/lib/datadog/di/instrumenter.rb
+++ b/lib/datadog/di/instrumenter.rb
@@ -304,13 +304,13 @@ def hook_line(probe, &block)
             end
           rescue => exc
             raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
-            logger.warn("Unhandled exception in line trace point: #{exc.class}: #{exc}")
+            logger.debug { "di: unhandled exception in line trace point: #{exc.class}: #{exc}" }
             telemetry&.report(exc, description: "Unhandled exception in line trace point")
             # TODO test this path
           end
         rescue => exc
           raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
-          logger.warn("Unhandled exception in line trace point: #{exc.class}: #{exc}")
+          logger.debug { "di: unhandled exception in line trace point: #{exc.class}: #{exc}" }
           telemetry&.report(exc, description: "Unhandled exception in line trace point")
           # TODO test this path
         end
@@ -356,7 +356,7 @@ def hook(probe, &block)
           hook_line(probe, &block)
         else
           # TODO add test coverage for this path
-          logger.warn("Unknown probe type to hook: #{probe}")
+          logger.debug { "di: unknown probe type to hook: #{probe}" }
         end
       end
 
@@ -367,7 +367,7 @@ def unhook(probe)
           unhook_line(probe)
         else
           # TODO add test coverage for this path
-          logger.warn("Unknown probe type to unhook: #{probe}")
+          logger.debug { "di: unknown probe type to unhook: #{probe}" }
         end
       end
 
diff --git a/lib/datadog/di/probe_manager.rb b/lib/datadog/di/probe_manager.rb
index 9dd74d85b5e..2567eb9803b 100644
--- a/lib/datadog/di/probe_manager.rb
+++ b/lib/datadog/di/probe_manager.rb
@@ -32,7 +32,7 @@ def initialize(settings, instrumenter, probe_notification_builder,
           install_pending_method_probes(tp.self)
         rescue => exc
           raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
-          logger.warn("Unhandled exception in definition trace point: #{exc.class}: #{exc}")
+          logger.debug { "di: unhandled exception in definition trace point: #{exc.class}: #{exc}" }
           telemetry&.report(exc, description: "Unhandled exception in definition trace point")
           # TODO test this path
         end
@@ -120,7 +120,7 @@ def add_probe(probe)
           # In "propagate all exceptions" mode we will try to instrument again.
           raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
 
-          logger.warn("Error processing probe configuration: #{exc.class}: #{exc}")
+          logger.debug { "di: error processing probe configuration: #{exc.class}: #{exc}" }
           telemetry&.report(exc, description: "Error processing probe configuration")
           # TODO report probe as failed to agent since we won't attempt to
           # install it again.
@@ -160,7 +160,7 @@ def remove_other_probes(probe_ids)
                 raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
                 # Silence all exceptions?
                 # TODO should we propagate here and rescue upstream?
-                logger.warn("Error removing probe #{probe.id}: #{exc.class}: #{exc}")
+                logger.debug { "di: error removing probe #{probe.id}: #{exc.class}: #{exc}" }
                 telemetry&.report(exc, description: "Error removing probe")
               end
             end
@@ -190,7 +190,7 @@ def remove_other_probes(probe_ids)
                 rescue => exc
                   raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
 
-                  logger.warn("Error installing probe after class is defined: #{exc.class}: #{exc}")
+                  logger.debug { "di: error installing probe after class is defined: #{exc.class}: #{exc}" }
                   telemetry&.report(exc, description: "Error installing probe after class is defined")
                 end
               end
diff --git a/lib/datadog/di/probe_notifier_worker.rb b/lib/datadog/di/probe_notifier_worker.rb
index b7cb2e78fba..03efaece9e0 100644
--- a/lib/datadog/di/probe_notifier_worker.rb
+++ b/lib/datadog/di/probe_notifier_worker.rb
@@ -77,7 +77,7 @@ def start
             rescue => exc
               raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
 
-              logger.warn("Error in probe notifier worker: #{exc.class}: #{exc} (at #{exc.backtrace.first})")
+              logger.debug { "di: error in probe notifier worker: #{exc.class}: #{exc} (at #{exc.backtrace.first})" }
               telemetry&.report(exc, description: "Error in probe notifier worker")
             end
             @lock.synchronize do
@@ -184,7 +184,7 @@ def io_in_progress?
           @lock.synchronize do
             queue = send("#{event_type}_queue")
             if queue.length > settings.dynamic_instrumentation.internal.snapshot_queue_capacity
-              logger.warn("#{self.class.name}: dropping #{event_type} because queue is full")
+              logger.debug { "di: #{self.class.name}: dropping #{event_type} because queue is full" }
             else
               queue << event
             end
@@ -241,7 +241,7 @@ def set_sleep_remaining
               end
             rescue => exc
               raise if settings.dynamic_instrumentation.internal.propagate_all_exceptions
-              logger.warn("failed to send #{event_name}: #{exc.class}: #{exc} (at #{exc.backtrace.first})")
+              logger.debug { "di: failed to send #{event_name}: #{exc.class}: #{exc} (at #{exc.backtrace.first})" }
               # Should we report this error to telemetry? Most likely failure
               # to send is due to a network issue, and trying to send a
               # telemetry message would also fail.
@@ -252,7 +252,7 @@ def set_sleep_remaining
           # Normally the queue should only be consumed in this method,
           # however if anyone consumes it elsewhere we don't want to block
           # while consuming it here. Rescue ThreadError and return.
-          logger.warn("Unexpected #{event_name} queue underflow - consumed elsewhere?")
+          logger.debug { "di: unexpected #{event_name} queue underflow - consumed elsewhere?" }
           telemetry&.report(exc, description: "Unexpected #{event_name} queue underflow")
         ensure
           @lock.synchronize do
diff --git a/lib/datadog/di/remote.rb b/lib/datadog/di/remote.rb
index e0a5f3b90ed..63a7751aa0c 100644
--- a/lib/datadog/di/remote.rb
+++ b/lib/datadog/di/remote.rb
@@ -51,7 +51,7 @@ def receivers(telemetry)
                     probe = ProbeBuilder.build_from_remote_config(probe_spec)
                     payload = component.probe_notification_builder.build_received(probe)
                     component.probe_notifier_worker.add_status(payload)
-                    component.logger.info("Received probe from RC: #{probe.type} #{probe.location}")
+                    component.logger.debug { "di: received probe from RC: #{probe.type} #{probe.location}" }
 
                     begin
                       # TODO test exception capture
@@ -60,7 +60,7 @@ def receivers(telemetry)
                     rescue => exc
                       raise if component.settings.dynamic_instrumentation.internal.propagate_all_exceptions
 
-                      component.logger.warn("Unhandled exception adding probe in DI remote receiver: #{exc.class}: #{exc}")
+                      component.logger.debug { "di: unhandled exception adding probe in DI remote receiver: #{exc.class}: #{exc}" }
                       component.telemetry&.report(exc, description: "Unhandled exception adding probe in DI remote receiver")
 
                       # If a probe fails to install, we will mark the content
@@ -81,7 +81,7 @@ def receivers(telemetry)
                   rescue => exc
                     raise if component.settings.dynamic_instrumentation.internal.propagate_all_exceptions
 
-                    component.logger.warn("Unhandled exception handling probe in DI remote receiver: #{exc.class}: #{exc}")
+                    component.logger.debug { "di: unhandled exception handling probe in DI remote receiver: #{exc.class}: #{exc}" }
                     component.telemetry&.report(exc, description: "Unhandled exception handling probe in DI remote receiver")
 
                     content.errored("Error applying dynamic instrumentation configuration: #{exc.class.name} #{exc.message}: #{Array(exc.backtrace).join("\n")}")
@@ -95,7 +95,7 @@ def receivers(telemetry)
               rescue => exc
                 raise if component.settings.dynamic_instrumentation.internal.propagate_all_exceptions
 
-                component.logger.warn("Unhandled exception removing probes in DI remote receiver: #{exc.class}: #{exc}")
+                component.logger.debug { "di: unhandled exception removing probes in DI remote receiver: #{exc.class}: #{exc}" }
                 component.telemetry&.report(exc, description: "Unhandled exception removing probes in DI remote receiver")
               end
             end
diff --git a/spec/datadog/di/component_spec.rb b/spec/datadog/di/component_spec.rb
index 0453fc8e4a8..96465563019 100644
--- a/spec/datadog/di/component_spec.rb
+++ b/spec/datadog/di/component_spec.rb
@@ -48,7 +48,7 @@
         end
 
         it 'returns nil' do
-          expect(logger).to receive(:debug).with(/Dynamic Instrumentation could not be enabled because Remote Configuration Management is not available/)
+          expect(logger).to receive(:warn).with(/dynamic instrumentation could not be enabled because Remote Configuration Management is not available/)
           component = described_class.build(settings, agent_settings, logger)
           expect(component).to be nil
         end
diff --git a/spec/datadog/di/instrumenter_spec.rb b/spec/datadog/di/instrumenter_spec.rb
index 93cc8aee457..c96c2e32716 100644
--- a/spec/datadog/di/instrumenter_spec.rb
+++ b/spec/datadog/di/instrumenter_spec.rb
@@ -784,7 +784,7 @@
         # Needed for the cleanup unhook call.
         allow(probe).to receive(:method?).and_return(false)
         allow(probe).to receive(:line?).and_return(false)
-        allow(logger).to receive(:warn)
+        allow(logger).to receive(:debug)
       end
 
       it 'raises ArgumentError' do
diff --git a/spec/datadog/di/integration/everything_from_remote_config_spec.rb b/spec/datadog/di/integration/everything_from_remote_config_spec.rb
index 499793a286e..7863c54bfe4 100644
--- a/spec/datadog/di/integration/everything_from_remote_config_spec.rb
+++ b/spec/datadog/di/integration/everything_from_remote_config_spec.rb
@@ -241,7 +241,7 @@ def do_rc
     end
 
     it 'adds a probe to pending list' do
-      expect(logger).to receive(:info).with(/Received probe from RC:/)
+      expect_lazy_log(logger, :debug, /received probe from RC:/)
 
       do_rc
 
@@ -272,7 +272,7 @@ def assert_received_and_installed
     end
 
     it 'instruments code and adds probe to installed list' do
-      expect(logger).to receive(:info).with(/Received probe from RC:/)
+      expect_lazy_log(logger, :debug, /received probe from RC:/)
 
       do_rc
       assert_received_and_installed
@@ -282,7 +282,7 @@ def assert_received_and_installed
 
     context 'and target method is invoked' do
       it 'notifies about execution' do
-        expect(logger).to receive(:info).with(/Received probe from RC:/)
+        expect_lazy_log(logger, :debug, /received probe from RC:/)
 
         do_rc
         assert_received_and_installed
@@ -325,8 +325,8 @@ def assert_received_and_installed
       end
 
       it 'installs the second, known, probe' do
-        expect(logger).to receive(:warn).with(/Unrecognized probe type:/)
-        expect(logger).to receive(:info).with(/Received probe from RC:/)
+        expect_lazy_log(logger, :debug, /Unrecognized probe type:/)
+        expect_lazy_log(logger, :debug, /received probe from RC:/)
 
         do_rc
         assert_received_and_installed
diff --git a/spec/datadog/di/probe_manager_spec.rb b/spec/datadog/di/probe_manager_spec.rb
index a6f7a1c8d8a..d9a5f75eeba 100644
--- a/spec/datadog/di/probe_manager_spec.rb
+++ b/spec/datadog/di/probe_manager_spec.rb
@@ -97,9 +97,7 @@ class ProbeManagerSpecTestClass; end
 
       context 'when there is an exception during instrumentation' do
         it 'logs warning, drops probe and reraises the exception' do
-          expect(logger).to receive(:warn) do |msg|
-            expect(msg).to match(/Error processing probe configuration.*Instrumentation error/)
-          end
+          expect_lazy_log(logger, :debug, /error processing probe configuration.*Instrumentation error/)
 
           expect(instrumenter).to receive(:hook) do |probe_|
             expect(probe_).to be(probe)
@@ -180,9 +178,7 @@ class ProbeManagerSpecTestClass; end
         it 'logs warning and keeps probe in installed list' do
           expect(instrumenter).to receive(:unhook).with(probe).and_raise("Deinstrumentation error")
 
-          expect(logger).to receive(:warn) do |msg|
-            expect(msg).to match(/Error removing probe.*Deinstrumentation error/)
-          end
+          expect_lazy_log(logger, :debug, /error removing probe.*Deinstrumentation error/)
 
           manager.remove_other_probes(['123'])
 
@@ -207,9 +203,7 @@ class ProbeManagerSpecTestClass; end
             expect(instrumenter).to receive(:unhook).with(probe).and_raise("Deinstrumentation error")
             expect(instrumenter).to receive(:unhook).with(probe2)
 
-            expect(logger).to receive(:warn) do |msg|
-              expect(msg).to match(/Error removing probe.*Deinstrumentation error/)
-            end
+            expect_lazy_log(logger, :debug, /error removing probe.*Deinstrumentation error/)
 
             manager.remove_other_probes(['123'])
 
diff --git a/spec/datadog/di/remote_spec.rb b/spec/datadog/di/remote_spec.rb
index 06368623d3a..677cd73c597 100644
--- a/spec/datadog/di/remote_spec.rb
+++ b/spec/datadog/di/remote_spec.rb
@@ -147,9 +147,7 @@
 
         it 'calls probe manager to add a probe' do
           expect(component).to receive(:logger).and_return(logger)
-          expect(logger).to receive(:info) do |message|
-            expect(message).to match(/Received probe/)
-          end
+          expect_lazy_log(logger, :debug, /received probe/)
 
           expect(probe_manager).to receive(:add_probe) do |probe|
             expect(probe.id).to eq('11')
@@ -165,13 +163,9 @@
           it 'logs warning and consumes the exception' do
             expect(component).to receive(:telemetry).and_return(telemetry)
             expect(component).to receive(:logger).and_return(logger)
-            expect(logger).to receive(:info) do |message|
-              expect(message).to match(/Received probe/)
-            end
+            expect_lazy_log(logger, :debug, /received probe/)
 
-            expect(logger).to receive(:warn) do |msg|
-              expect(msg).to match(/Unhandled exception.*Runtime error from test/)
-            end
+            expect_lazy_log(logger, :debug, /unhandled exception.*Runtime error from test/)
             expect(component).to receive(:logger).and_return(logger)
             expect(telemetry).to receive(:report)
 
@@ -189,13 +183,9 @@
         it 'calls probe manager to remove stale probes' do
           allow(component).to receive(:telemetry)
           expect(component).to receive(:logger).and_return(logger)
-          expect(logger).to receive(:info) do |message|
-            expect(message).to match(/Received probe/)
-          end
+          expect_lazy_log(logger, :debug, /received probe/)
 
-          expect(logger).to receive(:warn) do |msg|
-            expect(msg).to match(/Unhandled exception.*Runtime error from test/)
-          end
+          expect_lazy_log(logger, :debug, /unhandled exception.*Runtime error from test/)
 
           allow(probe_manager).to receive(:add_probe).and_raise("Runtime error from test")
           expect(component).to receive(:logger).and_return(logger)
@@ -212,13 +202,9 @@
           it 'logs warning and consumes the exception' do
             expect(component).to receive(:telemetry).and_return(telemetry).at_least(:once)
             expect(component).to receive(:logger).and_return(logger)
-            expect(logger).to receive(:info) do |message|
-              expect(message).to match(/Received probe/)
-            end
+            expect_lazy_log(logger, :debug, /received probe/)
 
-            expect(logger).to receive(:warn) do |msg|
-              expect(msg).to match(/Unhandled exception.*Runtime error 1 from test/)
-            end
+            expect_lazy_log(logger, :debug, /unhandled exception.*Runtime error 1 from test/)
             expect(telemetry).to receive(:report)
 
             allow(probe_manager).to receive(:add_probe).and_raise("Runtime error 1 from test")
@@ -228,9 +214,7 @@
             expect(component).to receive(:probe_notifier_worker).and_return(probe_notifier_worker)
             expect(probe_notifier_worker).to receive(:add_status)
 
-            expect(logger).to receive(:warn) do |msg|
-              expect(msg).to match(/Unhandled exception.*Runtime error 2 from test/)
-            end
+            expect_lazy_log(logger, :debug, /unhandled exception.*Runtime error 2 from test/)
             expect(component).to receive(:logger).and_return(logger)
             expect(telemetry).to receive(:report)
 
diff --git a/spec/datadog/di/spec_helper.rb b/spec/datadog/di/spec_helper.rb
index 09d8ffbd3c2..81fc72c9300 100644
--- a/spec/datadog/di/spec_helper.rb
+++ b/spec/datadog/di/spec_helper.rb
@@ -85,6 +85,16 @@ def deep_stringify_keys(hash)
     def instance_double_agent_settings
       instance_double(Datadog::Core::Configuration::AgentSettingsResolver::AgentSettings)
     end
+
+    def expect_lazy_log(logger, meth, expected_msg)
+      expect(logger).to receive(meth) do |&block|
+        if expected_msg.is_a?(String)
+          expect(block.call).to eq(expected_msg)
+        else
+          expect(block.call).to match(expected_msg)
+        end
+      end
+    end
   end
 end