diff --git a/lib/datadog/core/telemetry/component.rb b/lib/datadog/core/telemetry/component.rb
index 6324f8ac795..f457a434ce4 100644
--- a/lib/datadog/core/telemetry/component.rb
+++ b/lib/datadog/core/telemetry/component.rb
@@ -28,6 +28,7 @@ def initialize(heartbeat_interval_seconds:, dependency_collection:, enabled: tru
             heartbeat_interval_seconds: heartbeat_interval_seconds,
             emitter: Emitter.new
           )
+          @worker.start
         end
 
         def disable!
@@ -38,26 +39,24 @@ def disable!
         def started!
           return if !@enabled || forked?
 
-          @worker.start
           @worker.enqueue(Event::AppDependenciesLoaded.new) if @dependency_collection
 
           @started = true
         end
 
-        def emit_closing!
-          return if !@enabled || forked?
-
-          @worker.enqueue(Event::AppClosing.new)
-        end
-
         def stop!
           return if @stopped
 
-          # gracefully stop the worker and send leftover events
-          @worker.stop
+          @worker.stop(true)
           @stopped = true
         end
 
+        def emit_closing!
+          return if !@enabled || forked?
+
+          @worker.enqueue(Event::AppClosing.new)
+        end
+
         def integrations_change!
           return if !@enabled || forked?
 
diff --git a/lib/datadog/core/telemetry/worker.rb b/lib/datadog/core/telemetry/worker.rb
index da0bc7dd455..8ba8e8723b1 100644
--- a/lib/datadog/core/telemetry/worker.rb
+++ b/lib/datadog/core/telemetry/worker.rb
@@ -2,6 +2,7 @@
 
 require_relative 'event'
 
+require_relative '../utils/only_once_successful'
 require_relative '../workers/polling'
 require_relative '../workers/queue'
 
@@ -15,6 +16,8 @@ class Worker
 
         DEFAULT_BUFFER_MAX_SIZE = 1000
 
+        TELEMETRY_STARTED_ONCE = Utils::OnlyOnceSuccessful.new
+
         def initialize(
           heartbeat_interval_seconds:,
           emitter:,
@@ -24,8 +27,6 @@ def initialize(
         )
           @emitter = emitter
 
-          @sent_started_event = false
-
           # Workers::Polling settings
           self.enabled = enabled
           # Workers::IntervalLoop settings
@@ -48,6 +49,8 @@ def start
         def stop(force_stop = false, timeout = @shutdown_timeout)
           buffer.close if running?
 
+          flush_events(dequeue) if work_pending?
+
           super
         end
 
@@ -56,7 +59,7 @@ def enqueue(event)
         end
 
         def sent_started_event?
-          @sent_started_event
+          TELEMETRY_STARTED_ONCE.ran?
         end
 
         private
@@ -89,24 +92,25 @@ def heartbeat!
         def started!
           return unless enabled?
 
-          res = send_event(Event::AppStarted.new)
+          TELEMETRY_STARTED_ONCE.run do
+            res = send_event(Event::AppStarted.new)
 
-          if res.not_found? # Telemetry is only supported by agent versions 7.34 and up
-            Datadog.logger.debug('Agent does not support telemetry; disabling future telemetry events.')
-            self.enabled = false
-          elsif res.ok?
-            Datadog.logger.debug('Telemetry app-started event is successfully sent')
-            @sent_started_event = true
-          else
-            Datadog.logger.debug('Error sending telemetry app-started event, retry after heartbeat interval...')
+            if res.ok?
+              Datadog.logger.debug('Telemetry app-started event is successfully sent')
+              true
+            else
+              Datadog.logger.debug('Error sending telemetry app-started event, retry after heartbeat interval...')
+              false
+            end
           end
         end
 
         def send_event(event)
-          Datadog.logger.debug { "Sending telemetry event: #{event}" }
-          response = @emitter.request(event)
-          Datadog.logger.debug { "Received response: #{response}" }
-          response
+          res = @emitter.request(event)
+
+          disable_on_not_found!(res)
+
+          res
         end
 
         def dequeue
@@ -120,6 +124,13 @@ def buffer_klass
             Core::Buffer::ThreadSafe
           end
         end
+
+        def disable_on_not_found!(response)
+          return unless response.not_found?
+
+          Datadog.logger.debug('Agent does not support telemetry; disabling future telemetry events.')
+          self.enabled = false
+        end
       end
     end
   end
diff --git a/sig/datadog/core/telemetry/worker.rbs b/sig/datadog/core/telemetry/worker.rbs
index 9220dfeea09..b804a19664d 100644
--- a/sig/datadog/core/telemetry/worker.rbs
+++ b/sig/datadog/core/telemetry/worker.rbs
@@ -8,6 +8,7 @@ module Datadog
         include Core::Workers::IntervalLoop
         include Core::Workers::Queue
 
+        TELEMETRY_STARTED_ONCE: Datadog::Core::Utils::OnlyOnceSuccessful
         DEFAULT_BUFFER_MAX_SIZE: 1000
 
         @emitter: Emitter
@@ -23,6 +24,8 @@ module Datadog
 
         def enqueue: (Event::Base event) -> void
 
+        def dequeue: () -> Array[Event::Base]
+
         private
 
         def heartbeat!: () -> void
@@ -33,6 +36,8 @@ module Datadog
 
         def send_event: (Event::Base event) -> Datadog::Core::Telemetry::Http::Adapters::Net::Response
 
+        def disable_on_not_found!: (Datadog::Core::Telemetry::Http::Adapters::Net::Response response) -> void
+
         def buffer_klass: () -> untyped
       end
     end
diff --git a/spec/datadog/core/telemetry/component_spec.rb b/spec/datadog/core/telemetry/component_spec.rb
index 5d1f7f013f7..33f4544ec6e 100644
--- a/spec/datadog/core/telemetry/component_spec.rb
+++ b/spec/datadog/core/telemetry/component_spec.rb
@@ -82,7 +82,7 @@
       it do
         started!
 
-        expect(worker).to_not have_received(:start)
+        expect(worker).to_not have_received(:enqueue)
       end
     end
 
@@ -118,7 +118,7 @@
         expect_in_fork do
           telemetry.started!
 
-          expect(worker).to_not have_received(:start)
+          expect(worker).to_not have_received(:enqueue)
         end
       end
     end
diff --git a/spec/datadog/core/telemetry/worker_spec.rb b/spec/datadog/core/telemetry/worker_spec.rb
index ba389c23801..6008cefd892 100644
--- a/spec/datadog/core/telemetry/worker_spec.rb
+++ b/spec/datadog/core/telemetry/worker_spec.rb
@@ -42,8 +42,10 @@
   end
 
   after do
-    worker.stop(true, 0)
+    worker.stop(true)
     worker.join
+
+    Datadog::Core::Telemetry::Worker::TELEMETRY_STARTED_ONCE.send(:reset_ran_once_state_for_tests)
   end
 
   describe '.new' do
@@ -97,19 +99,19 @@
         end
 
         it 'always sends heartbeat event after started event' do
-          @sent_hearbeat = false
+          sent_hearbeat = false
           allow(emitter).to receive(:request).with(kind_of(Datadog::Core::Telemetry::Event::AppHeartbeat)) do
             # app-started was already sent by now
             expect(worker.sent_started_event?).to be(true)
 
-            @sent_hearbeat = true
+            sent_hearbeat = true
 
             response
           end
 
           worker.start
 
-          try_wait_until { @sent_hearbeat }
+          try_wait_until { sent_hearbeat }
         end
       end
 
@@ -124,6 +126,42 @@
           expect(@received_heartbeat).to be(false)
         end
       end
+
+      context 'several workers running' do
+        it 'sends single started event' do
+          started_events = 0
+          allow(emitter).to receive(:request).with(kind_of(Datadog::Core::Telemetry::Event::AppStarted)) do
+            started_events += 1
+
+            response
+          end
+
+          heartbeat_events = 0
+          allow(emitter).to receive(:request).with(kind_of(Datadog::Core::Telemetry::Event::AppHeartbeat)) do
+            heartbeat_events += 1
+
+            response
+          end
+
+          workers = Array.new(3) do
+            described_class.new(
+              enabled: enabled,
+              heartbeat_interval_seconds: heartbeat_interval_seconds,
+              emitter: emitter
+            )
+          end
+          workers.each(&:start)
+
+          try_wait_until { heartbeat_events >= 3 }
+
+          expect(started_events).to be(1)
+
+          workers.each do |w|
+            w.stop(true, 0)
+            w.join
+          end
+        end
+      end
     end
 
     context 'when disabled' do
@@ -137,6 +175,36 @@
     end
   end
 
+  describe '#stop' do
+    let(:heartbeat_interval_seconds) { 3 }
+
+    it 'flushes events and stops the worker' do
+      events_received = 0
+      allow(emitter).to receive(:request).with(
+        an_instance_of(Datadog::Core::Telemetry::Event::AppIntegrationsChange)
+      ) do
+        events_received += 1
+
+        response
+      end
+
+      worker.start
+
+      worker.enqueue(Datadog::Core::Telemetry::Event::AppIntegrationsChange.new)
+      worker.stop(true)
+
+      try_wait_until { !worker.running? }
+
+      expect(worker).to have_attributes(
+        enabled?: true,
+        loop_base_interval: heartbeat_interval_seconds,
+        run_async?: false,
+        running?: false,
+        started?: true
+      )
+    end
+  end
+
   describe '#enqueue' do
     it 'adds events to the buffer and flushes them later' do
       events_received = 0
@@ -144,6 +212,8 @@
         an_instance_of(Datadog::Core::Telemetry::Event::AppIntegrationsChange)
       ) do
         events_received += 1
+
+        response
       end
 
       worker.start