diff --git a/lib/datadog/di.rb b/lib/datadog/di.rb
index ff185b09318..e0681e6667e 100644
--- a/lib/datadog/di.rb
+++ b/lib/datadog/di.rb
@@ -58,6 +58,8 @@ def component
   #
   # If DI is enabled programmatically, the application can (and must,
   # for line probes to work) activate tracking in an initializer.
+  # We seem to have Datadog.logger here already
+  Datadog.logger.debug("di: activating code tracking")
   Datadog::DI.activate_tracking
 end
 
diff --git a/lib/datadog/di/contrib.rb b/lib/datadog/di/contrib.rb
index 8098b5befb0..0352b72b58e 100644
--- a/lib/datadog/di/contrib.rb
+++ b/lib/datadog/di/contrib.rb
@@ -7,6 +7,7 @@ module DI
     module Contrib
       module_function def load_now_or_later
         if Datadog::Core::Contrib::Rails::Utils.railtie_supported?
+          Datadog.logger.debug('di: loading contrib/railtie')
           require_relative 'contrib/railtie'
         else
           load_now
@@ -18,6 +19,7 @@ module Contrib
       # dependencies are loaded (or potentially loaded).
       module_function def load_now
         if defined?(ActiveRecord::Base)
+          Datadog.logger.debug('di: loading contrib/active_record')
           require_relative 'contrib/active_record'
         end
       end
diff --git a/lib/datadog/di/probe_manager.rb b/lib/datadog/di/probe_manager.rb
index 2567eb9803b..9faccbb41d3 100644
--- a/lib/datadog/di/probe_manager.rb
+++ b/lib/datadog/di/probe_manager.rb
@@ -111,9 +111,11 @@ def add_probe(probe)
             # Always remove from pending list here because it makes the
             # API smaller and shouldn't cause any actual problems.
             @pending_probes.delete(probe.id)
+            logger.debug { "di: installed #{probe.type} probe at #{probe.location}" }
             true
           rescue Error::DITargetNotDefined
             @pending_probes[probe.id] = probe
+            logger.debug { "di: could not install #{probe.type} probe at #{probe.location} because its target is not defined, adding it to pending list" }
             false
           end
         rescue => exc
diff --git a/lib/datadog/di/probe_notifier_worker.rb b/lib/datadog/di/probe_notifier_worker.rb
index 03efaece9e0..ae4703dc64e 100644
--- a/lib/datadog/di/probe_notifier_worker.rb
+++ b/lib/datadog/di/probe_notifier_worker.rb
@@ -10,7 +10,7 @@ module DI
     # The loop inside the worker rescues all exceptions to prevent termination
     # due to unhandled exceptions raised by any downstream code.
     # This includes communication and protocol errors when sending the
-    # payloads to the agent.
+    # events to the agent.
     #
     # The worker groups the data to send into batches. The goal is to perform
     # no more than one network operation per event type per second.
@@ -45,6 +45,7 @@ def initialize(settings, transport, logger, telemetry: nil)
 
       def start
         return if @thread
+        logger.debug("di: starting probe notifier: pid #{$$}")
         @thread = Thread.new do
           loop do
             # TODO If stop is requested, we stop immediately without
@@ -94,6 +95,7 @@ def start
       # to killing the thread using Thread#kill.
       def stop(timeout = 1)
         @stop_requested = true
+        logger.debug("di: stopping probe notifier")
         wake.signal
         if thread
           unless thread.join(timeout)
@@ -234,6 +236,7 @@ def set_sleep_remaining
           end
           if batch.any? # steep:ignore
             begin
+              logger.debug { "di: sending #{batch.length} #{event_type} events to agent" }
               transport.public_send("send_#{event_type}", batch)
               time = Core::Utils::Time.get_time
               @lock.synchronize do
diff --git a/lib/datadog/di/remote.rb b/lib/datadog/di/remote.rb
index 1e5a0b8aa14..bb455f7352e 100644
--- a/lib/datadog/di/remote.rb
+++ b/lib/datadog/di/remote.rb
@@ -53,7 +53,7 @@ def receivers(telemetry)
                     payload = probe_notification_builder.build_received(probe)
                     probe_notifier_worker = component.probe_notifier_worker
                     probe_notifier_worker.add_status(payload)
-                    component.logger.debug { "di: received probe from RC: #{probe.type} #{probe.location}" }
+                    component.logger.debug { "di: received probe from RC: #{probe.type} at #{probe.location}" }
 
                     begin
                       # TODO test exception capture