diff --git a/lib/datadog/core/metrics/client.rb b/lib/datadog/core/metrics/client.rb
index cb180d7de2d..cde34bb32db 100644
--- a/lib/datadog/core/metrics/client.rb
+++ b/lib/datadog/core/metrics/client.rb
@@ -2,6 +2,7 @@
 
 require_relative '../utils/time'
 require_relative '../utils/only_once'
+require_relative '../telemetry/logger'
 require_relative '../configuration/ext'
 
 require_relative 'ext'
@@ -100,6 +101,7 @@ def count(stat, value = nil, options = nil, &block)
           Datadog.logger.error(
             "Failed to send count stat. Cause: #{e.class.name} #{e.message} Source: #{Array(e.backtrace).first}"
           )
+          Telemetry::Logger.report(e, description: 'Failed to send count stat')
         end
 
         def distribution(stat, value = nil, options = nil, &block)
@@ -113,6 +115,7 @@ def distribution(stat, value = nil, options = nil, &block)
           Datadog.logger.error(
             "Failed to send distribution stat. Cause: #{e.class.name} #{e.message} Source: #{Array(e.backtrace).first}"
           )
+          Telemetry::Logger.report(e, description: 'Failed to send distribution stat')
         end
 
         def increment(stat, options = nil)
@@ -125,6 +128,7 @@ def increment(stat, options = nil)
           Datadog.logger.error(
             "Failed to send increment stat. Cause: #{e.class.name} #{e.message} Source: #{Array(e.backtrace).first}"
           )
+          Telemetry::Logger.report(e, description: 'Failed to send increment stat')
         end
 
         def gauge(stat, value = nil, options = nil, &block)
@@ -138,6 +142,7 @@ def gauge(stat, value = nil, options = nil, &block)
           Datadog.logger.error(
             "Failed to send gauge stat. Cause: #{e.class.name} #{e.message} Source: #{Array(e.backtrace).first}"
           )
+          Telemetry::Logger.report(e, description: 'Failed to send gauge stat')
         end
 
         def time(stat, options = nil)
@@ -153,9 +158,11 @@ def time(stat, options = nil)
               distribution(stat, ((finished - start) * 1000), options)
             end
           rescue StandardError => e
+            # TODO: Likely to be redundant, since `distribution` handles its own errors.
             Datadog.logger.error(
               "Failed to send time stat. Cause: #{e.class.name} #{e.message} Source: #{Array(e.backtrace).first}"
             )
+            Telemetry::Logger.report(e, description: 'Failed to send time stat')
           end
         end
 
diff --git a/lib/datadog/core/remote/component.rb b/lib/datadog/core/remote/component.rb
index b468ee9dbdc..3c8047cc9d3 100644
--- a/lib/datadog/core/remote/component.rb
+++ b/lib/datadog/core/remote/component.rb
@@ -39,6 +39,7 @@ def initialize(settings, capabilities, agent_settings)
               @client.sync
               @healthy ||= true
             rescue Client::SyncError => e
+              # Transient errors due to network or agent. Logged the error but not via telemetry
               Datadog.logger.error do
                 "remote worker client sync error: #{e.message} location: #{Array(e.backtrace).first}. skipping sync"
               end
@@ -48,6 +49,7 @@ def initialize(settings, capabilities, agent_settings)
               # negotiation object stores error logging state that should be reset.
               negotiation = Negotiation.new(settings, agent_settings)
 
+              # Transient errors due to network or agent. Logged the error but not via telemetry
               Datadog.logger.error do
                 "remote worker error: #{e.class.name} #{e.message} location: #{Array(e.backtrace).first}. "\
                 'reseting client state'
diff --git a/lib/datadog/core/remote/negotiation.rb b/lib/datadog/core/remote/negotiation.rb
index a43eb80a334..d68de4f40b6 100644
--- a/lib/datadog/core/remote/negotiation.rb
+++ b/lib/datadog/core/remote/negotiation.rb
@@ -20,7 +20,7 @@ def endpoint?(path)
 
           if res.internal_error? && network_error?(res.error)
             unless @logged[:agent_unreachable]
-              Datadog.logger.error { "agent unreachable: cannot negotiate #{path}" }
+              Datadog.logger.warn { "agent unreachable: cannot negotiate #{path}" }
               @logged[:agent_unreachable] = true
             end
 
@@ -29,7 +29,7 @@ def endpoint?(path)
 
           if res.not_found?
             unless @logged[:no_info_endpoint]
-              Datadog.logger.error { "agent reachable but has no /info endpoint: cannot negotiate #{path}" }
+              Datadog.logger.warn { "agent reachable but has no /info endpoint: cannot negotiate #{path}" }
               @logged[:no_info_endpoint] = true
             end
 
@@ -38,7 +38,7 @@ def endpoint?(path)
 
           unless res.ok?
             unless @logged[:unexpected_response]
-              Datadog.logger.error { "agent reachable but unexpected response: cannot negotiate #{path}" }
+              Datadog.logger.warn { "agent reachable but unexpected response: cannot negotiate #{path}" }
               @logged[:unexpected_response] = true
             end
 
@@ -47,7 +47,7 @@ def endpoint?(path)
 
           unless res.endpoints.include?(path)
             unless @logged[:no_config_endpoint]
-              Datadog.logger.error { "agent reachable but does not report #{path}" }
+              Datadog.logger.warn { "agent reachable but does not report #{path}" }
               @logged[:no_config_endpoint] = true
             end
 
diff --git a/lib/datadog/core/runtime/metrics.rb b/lib/datadog/core/runtime/metrics.rb
index c07c75319e4..6c89d5b7dc7 100644
--- a/lib/datadog/core/runtime/metrics.rb
+++ b/lib/datadog/core/runtime/metrics.rb
@@ -94,7 +94,7 @@ def gc_metrics
         def try_flush
           yield
         rescue StandardError => e
-          Datadog.logger.error("Error while sending runtime metric. Cause: #{e.class.name} #{e.message}")
+          Datadog.logger.warn("Error while sending runtime metric. Cause: #{e.class.name} #{e.message}")
         end
 
         def default_metric_options
diff --git a/lib/datadog/core/telemetry/event.rb b/lib/datadog/core/telemetry/event.rb
index 3808c475893..fabc8014207 100644
--- a/lib/datadog/core/telemetry/event.rb
+++ b/lib/datadog/core/telemetry/event.rb
@@ -1,5 +1,8 @@
 # frozen_string_literal: true
 
+require_relative '../utils/forking'
+require_relative '../utils/sequence'
+
 module Datadog
   module Core
     module Telemetry
diff --git a/lib/datadog/opentelemetry/sdk/propagator.rb b/lib/datadog/opentelemetry/sdk/propagator.rb
index f45e4e9d7f4..b711fba2390 100644
--- a/lib/datadog/opentelemetry/sdk/propagator.rb
+++ b/lib/datadog/opentelemetry/sdk/propagator.rb
@@ -15,6 +15,7 @@ def inject(
           setter: ::OpenTelemetry::Context::Propagation.text_map_setter
         )
           unless setter == ::OpenTelemetry::Context::Propagation.text_map_setter
+            # PENDING: Not to report telemetry logs for now
             Datadog.logger.error(
               'Custom setter is not supported. Please inform the `datadog` team at ' \
             ' https://github.com/DataDog/dd-trace-rb of your use case so we can best support you. Using the default ' \
@@ -31,6 +32,7 @@ def extract(
         )
           if getter != ::OpenTelemetry::Context::Propagation.text_map_getter &&
               getter != ::OpenTelemetry::Common::Propagation.rack_env_getter
+            # PENDING: Not to report telemetry logs for now
             Datadog.logger.error(
               "Custom getter #{getter} is not supported. Please inform the `datadog` team at " \
             ' https://github.com/DataDog/dd-trace-rb of your use case so we can best support you. Using the default ' \
diff --git a/lib/datadog/tracing/distributed/propagation.rb b/lib/datadog/tracing/distributed/propagation.rb
index 2c56b441220..9ab993eb56e 100644
--- a/lib/datadog/tracing/distributed/propagation.rb
+++ b/lib/datadog/tracing/distributed/propagation.rb
@@ -3,6 +3,7 @@
 require_relative '../configuration/ext'
 require_relative '../trace_digest'
 require_relative '../trace_operation'
+require_relative '../../core/telemetry/logger'
 
 module Datadog
   module Tracing
@@ -72,6 +73,10 @@ def inject!(digest, data)
             ::Datadog.logger.error(
               "Error injecting distributed trace data. Cause: #{e} Location: #{Array(e.backtrace).first}"
             )
+            ::Datadog::Core::Telemetry::Logger.report(
+              e,
+              description: "Error injecting distributed trace data with #{propagator.class.name}"
+            )
           end
 
           result
@@ -127,6 +132,7 @@ def extract(data)
               )
             end
           rescue => e
+            # TODO: Not to report Telemetry logs for now
             ::Datadog.logger.error(
               "Error extracting distributed trace data. Cause: #{e} Location: #{Array(e.backtrace).first}"
             )
diff --git a/lib/datadog/tracing/sampling/rate_sampler.rb b/lib/datadog/tracing/sampling/rate_sampler.rb
index bc79714bcec..ea581dd70fa 100644
--- a/lib/datadog/tracing/sampling/rate_sampler.rb
+++ b/lib/datadog/tracing/sampling/rate_sampler.rb
@@ -20,7 +20,7 @@ def initialize(sample_rate = 1.0, decision: nil)
           super()
 
           unless sample_rate >= 0.0 && sample_rate <= 1.0
-            Datadog.logger.error('sample rate is not between 0 and 1, falling back to 1')
+            Datadog.logger.warn('sample rate is not between 0 and 1, falling back to 1')
             sample_rate = 1.0
           end
 
diff --git a/lib/datadog/tracing/sampling/rule.rb b/lib/datadog/tracing/sampling/rule.rb
index 9c18bed7fac..6f458ba093f 100644
--- a/lib/datadog/tracing/sampling/rule.rb
+++ b/lib/datadog/tracing/sampling/rule.rb
@@ -2,6 +2,7 @@
 
 require_relative 'matcher'
 require_relative 'rate_sampler'
+require_relative '../../core/telemetry/logger'
 
 module Datadog
   module Tracing
@@ -35,6 +36,7 @@ def match?(trace)
           Datadog.logger.error(
             "Matcher failed. Cause: #{e.class.name} #{e.message} Source: #{Array(e.backtrace).first}"
           )
+          Datadog::Core::Telemetry::Logger.report(e, description: 'Matcher failed')
           nil
         end
 
diff --git a/lib/datadog/tracing/sampling/rule_sampler.rb b/lib/datadog/tracing/sampling/rule_sampler.rb
index 4b7e812e75f..398926233e3 100644
--- a/lib/datadog/tracing/sampling/rule_sampler.rb
+++ b/lib/datadog/tracing/sampling/rule_sampler.rb
@@ -3,6 +3,7 @@
 require_relative 'ext'
 require_relative '../../core/rate_limiter'
 require_relative 'rule'
+require_relative '../../core/telemetry/logger'
 
 module Datadog
   module Tracing
@@ -80,9 +81,10 @@ def self.parse(rules, rate_limit, default_sample_rate)
 
           new(parsed_rules, rate_limit: rate_limit, default_sample_rate: default_sample_rate)
         rescue => e
-          Datadog.logger.error do
+          Datadog.logger.warn do
             "Could not parse trace sampling rules '#{rules}': #{e.class.name} #{e.message} at #{Array(e.backtrace).first}"
           end
+
           nil
         end
 
@@ -140,6 +142,8 @@ def sample_trace(trace)
           Datadog.logger.error(
             "Rule sampling failed. Cause: #{e.class.name} #{e.message} Source: #{Array(e.backtrace).first}"
           )
+          Datadog::Core::Telemetry::Logger.report(e, description: 'Rule sampling failed')
+
           yield(trace)
         end
 
diff --git a/lib/datadog/tracing/transport/http/client.rb b/lib/datadog/tracing/transport/http/client.rb
index e19491ddabc..ab2c7191df8 100644
--- a/lib/datadog/tracing/transport/http/client.rb
+++ b/lib/datadog/tracing/transport/http/client.rb
@@ -38,6 +38,7 @@ def send_request(request, &block)
             if stats.consecutive_errors > 0
               Datadog.logger.debug(message)
             else
+              # Not to report telemetry logs
               Datadog.logger.error(message)
             end
 
diff --git a/lib/datadog/tracing/transport/io/client.rb b/lib/datadog/tracing/transport/io/client.rb
index 685c7512190..4288889ec76 100644
--- a/lib/datadog/tracing/transport/io/client.rb
+++ b/lib/datadog/tracing/transport/io/client.rb
@@ -49,6 +49,7 @@ def send_request(request)
             if stats.consecutive_errors > 0
               Datadog.logger.debug(message)
             else
+              # Not to report telemetry logs
               Datadog.logger.error(message)
             end
 
diff --git a/lib/datadog/tracing/workers.rb b/lib/datadog/tracing/workers.rb
index fdcce6772ba..030986a2204 100644
--- a/lib/datadog/tracing/workers.rb
+++ b/lib/datadog/tracing/workers.rb
@@ -56,7 +56,7 @@ def callback_traces
             # ensures that the thread will not die because of an exception.
             # TODO[manu]: findout the reason and reschedule the send if it's not
             # a fatal exception
-            Datadog.logger.error(
+            Datadog.logger.warn(
               "Error during traces flush: dropped #{traces.length} items. Cause: #{e} Location: #{Array(e.backtrace).first}"
             )
           end
diff --git a/lib/datadog/tracing/workers/trace_writer.rb b/lib/datadog/tracing/workers/trace_writer.rb
index fda409e74e5..bbb04ff219a 100644
--- a/lib/datadog/tracing/workers/trace_writer.rb
+++ b/lib/datadog/tracing/workers/trace_writer.rb
@@ -43,7 +43,7 @@ def write_traces(traces)
           traces = process_traces(traces)
           flush_traces(traces)
         rescue StandardError => e
-          Datadog.logger.error(
+          Datadog.logger.warn(
             "Error while writing traces: dropped #{traces.length} items. Cause: #{e} Location: #{Array(e.backtrace).first}"
           )
         end
diff --git a/spec/datadog/core/metrics/client_spec.rb b/spec/datadog/core/metrics/client_spec.rb
index 5f6fb218b2c..91af802a322 100644
--- a/spec/datadog/core/metrics/client_spec.rb
+++ b/spec/datadog/core/metrics/client_spec.rb
@@ -13,9 +13,16 @@
 
   it { is_expected.to have_attributes(statsd: statsd) }
 
-  shared_examples_for 'missing value arg' do
-    it 'logs an error without raising' do
-      expect(Datadog.logger).to receive(:error)
+  shared_examples_for 'logs an error without raising' do |action|
+    it do
+      expect(Datadog.logger).to receive(:error).with(
+        /Failed to send #{action} stat/
+      )
+      expect(Datadog::Core::Telemetry::Logger).to receive(:report).with(
+        a_kind_of(StandardError),
+        description: "Failed to send #{action} stat"
+      )
+
       expect { subject }.to_not raise_error
     end
   end
@@ -383,7 +390,7 @@
         context 'that does not yield args' do
           subject(:count) { metrics.count(stat) {} }
 
-          it_behaves_like 'missing value arg'
+          it_behaves_like 'logs an error without raising', 'count'
         end
 
         context 'that yields args' do
@@ -433,12 +440,9 @@
       end
 
       context 'which raises an error' do
-        before do
-          expect(statsd).to receive(:count).and_raise(StandardError)
-          expect(Datadog.logger).to receive(:error)
-        end
+        before { allow(statsd).to receive(:count).and_raise(StandardError) }
 
-        it { expect { count }.to_not raise_error }
+        it_behaves_like 'logs an error without raising', 'count'
       end
     end
   end
@@ -464,7 +468,7 @@
         context 'that does not yield args' do
           subject(:distribution) { metrics.distribution(stat) {} }
 
-          it_behaves_like 'missing value arg'
+          it_behaves_like 'logs an error without raising', 'distribution'
         end
 
         context 'that yields args' do
@@ -514,12 +518,9 @@
       end
 
       context 'which raises an error' do
-        before do
-          expect(statsd).to receive(:distribution).and_raise(StandardError)
-          expect(Datadog.logger).to receive(:error)
-        end
+        before { allow(statsd).to receive(:distribution).and_raise(StandardError) }
 
-        it { expect { distribution }.to_not raise_error }
+        it_behaves_like 'logs an error without raising', 'distribution'
       end
     end
   end
@@ -545,7 +546,7 @@
         context 'that does not yield args' do
           subject(:gauge) { metrics.gauge(stat) {} }
 
-          it_behaves_like 'missing value arg'
+          it_behaves_like 'logs an error without raising', 'gauge'
         end
 
         context 'that yields args' do
@@ -595,12 +596,9 @@
       end
 
       context 'which raises an error' do
-        before do
-          expect(statsd).to receive(:gauge).and_raise(StandardError)
-          expect(Datadog.logger).to receive(:error)
-        end
+        before { allow(statsd).to receive(:gauge).and_raise(StandardError) }
 
-        it { expect { gauge }.to_not raise_error }
+        it_behaves_like 'logs an error without raising', 'gauge'
       end
     end
   end
@@ -622,6 +620,12 @@
 
     context 'when #statsd is a Datadog::Statsd' do
       context 'and given a block' do
+        context 'when raise exception' do
+          subject(:increment) { metrics.increment(stat) { raise } }
+
+          it_behaves_like 'logs an error without raising', 'increment'
+        end
+
         context 'that yields args' do
           subject(:increment) { metrics.increment(stat) { stat_options } }
 
@@ -676,12 +680,9 @@
       end
 
       context 'which raises an error' do
-        before do
-          expect(statsd).to receive(:increment).and_raise(StandardError)
-          expect(Datadog.logger).to receive(:error)
-        end
+        before { allow(statsd).to receive(:increment).and_raise(StandardError) }
 
-        it { expect { increment }.to_not raise_error }
+        it_behaves_like 'logs an error without raising', 'increment'
       end
     end
   end
@@ -711,7 +712,10 @@
           let(:error) { RuntimeError.new }
           # Expect the given block to raise its errors through
 
-          it { expect { time }.to raise_error(error) }
+          it do
+            expect(Datadog.logger).not_to receive(:error)
+            expect { time }.to raise_error(error)
+          end
         end
       end
 
diff --git a/spec/datadog/core/remote/negotiation_spec.rb b/spec/datadog/core/remote/negotiation_spec.rb
index e34a0af2d59..71770a6ce51 100644
--- a/spec/datadog/core/remote/negotiation_spec.rb
+++ b/spec/datadog/core/remote/negotiation_spec.rb
@@ -50,13 +50,13 @@
       end
 
       it do
-        expect(Datadog.logger).to_not receive(:error)
+        expect(Datadog.logger).to_not receive(:warn)
 
         expect(endpoint?).to be true
       end
 
       it do
-        expect(Datadog.logger).to receive(:error).and_return(nil)
+        expect(Datadog.logger).to receive(:warn)
 
         expect(negotiation.endpoint?('/bar')).to be false
       end
@@ -65,7 +65,7 @@
         let(:suppress_logging) { { no_config_endpoint: true } }
 
         it 'does not log an error' do
-          expect(Datadog.logger).to_not receive(:error)
+          expect(Datadog.logger).to_not receive(:warn)
 
           expect(negotiation.endpoint?('/bar')).to be false
         end
@@ -77,7 +77,7 @@
       let(:response_body) { '404 page not found' }
 
       before do
-        expect(Datadog.logger).to receive(:error).and_return(nil)
+        expect(Datadog.logger).to receive(:warn)
       end
 
       it { expect(endpoint?).to be false }
@@ -95,7 +95,7 @@
       let(:response_body) { '400 bad request' }
 
       before do
-        expect(Datadog.logger).to receive(:error).and_return(nil)
+        expect(Datadog.logger).to receive(:warn)
       end
 
       it { expect(endpoint?).to be false }
@@ -113,7 +113,7 @@
       let(:response_body) { '500 internal server error' }
 
       before do
-        expect(Datadog.logger).to receive(:error).and_return(nil)
+        expect(Datadog.logger).to receive(:warn)
       end
 
       it { expect(endpoint?).to be false }
@@ -133,7 +133,7 @@
       end
 
       before do
-        expect(Datadog.logger).to receive(:error).and_return(nil)
+        expect(Datadog.logger).to receive(:warn)
       end
 
       it { expect(endpoint?).to be false }
@@ -150,7 +150,7 @@
       let(:request_exception) { Errno::ECONNREFUSED.new }
 
       before do
-        expect(Datadog.logger).to receive(:error).and_return(nil)
+        expect(Datadog.logger).to receive(:warn)
       end
 
       it { expect(endpoint?).to be false }
diff --git a/spec/datadog/core/runtime/metrics_spec.rb b/spec/datadog/core/runtime/metrics_spec.rb
index 13488814f9b..f3480969ef4 100644
--- a/spec/datadog/core/runtime/metrics_spec.rb
+++ b/spec/datadog/core/runtime/metrics_spec.rb
@@ -98,7 +98,7 @@
       end
 
       context 'when an error is thrown' do
-        before { allow(Datadog.logger).to receive(:error) }
+        before { allow(Datadog.logger).to receive(:warn) }
 
         it do
           allow(metric).to receive(:available?)
@@ -106,7 +106,7 @@
 
           flush
 
-          expect(Datadog.logger).to have_received(:error)
+          expect(Datadog.logger).to have_received(:warn)
             .with(/Error while sending runtime metric./)
             .at_least(:once)
         end
diff --git a/spec/datadog/tracing/sampling/rate_sampler_spec.rb b/spec/datadog/tracing/sampling/rate_sampler_spec.rb
index 5c26c02b47f..993efb1d0b4 100644
--- a/spec/datadog/tracing/sampling/rate_sampler_spec.rb
+++ b/spec/datadog/tracing/sampling/rate_sampler_spec.rb
@@ -22,6 +22,12 @@
         it_behaves_like 'sampler with sample rate', 1.0 do
           let(:trace) { nil }
         end
+
+        it do
+          expect(Datadog.logger).to receive(:warn).with('sample rate is not between 0 and 1, falling back to 1')
+
+          sampler
+        end
       end
 
       context 'that is 0' do
@@ -46,6 +52,12 @@
         let(:sample_rate) { 1.5 }
 
         it_behaves_like 'sampler with sample rate', 1.0
+
+        it do
+          expect(Datadog.logger).to receive(:warn).with('sample rate is not between 0 and 1, falling back to 1')
+
+          sampler
+        end
       end
     end
   end
diff --git a/spec/datadog/tracing/sampling/rule_sampler_spec.rb b/spec/datadog/tracing/sampling/rule_sampler_spec.rb
index 43c2ea25d22..e63e2e9d6ca 100644
--- a/spec/datadog/tracing/sampling/rule_sampler_spec.rb
+++ b/spec/datadog/tracing/sampling/rule_sampler_spec.rb
@@ -173,7 +173,7 @@
       let(:rule) { { sample_rate: 'oops' } }
 
       it 'does not accept rule with a non-float sample_rate' do
-        expect(Datadog.logger).to receive(:error)
+        expect(Datadog.logger).to receive(:warn)
         is_expected.to be_nil
       end
     end
@@ -182,7 +182,7 @@
       let(:rule) { { name: 'test' } }
 
       it 'does not accept rule missing the mandatory sample_rate' do
-        expect(Datadog.logger).to receive(:error)
+        expect(Datadog.logger).to receive(:warn)
         is_expected.to be_nil
       end
 
@@ -190,7 +190,7 @@
         let(:rules) { [{ sample_rate: 0.1 }, { name: 'test' }] }
 
         it 'rejects all rules if one is missing the mandatory sample_rate' do
-          expect(Datadog.logger).to receive(:error)
+          expect(Datadog.logger).to receive(:warn)
           is_expected.to be_nil
         end
       end
@@ -200,7 +200,7 @@
       let(:rules) { 'not a json array' }
 
       it 'returns nil in case of parsing error' do
-        expect(Datadog.logger).to receive(:error)
+        expect(Datadog.logger).to receive(:warn)
         is_expected.to be_nil
       end
     end
diff --git a/spec/datadog/tracing/sampling/rule_spec.rb b/spec/datadog/tracing/sampling/rule_spec.rb
index 6451c32e51d..305eb4a41ac 100644
--- a/spec/datadog/tracing/sampling/rule_spec.rb
+++ b/spec/datadog/tracing/sampling/rule_spec.rb
@@ -53,6 +53,8 @@
 
         expect(Datadog.logger).to receive(:error)
           .with(a_string_including("Matcher failed. Cause: #{error}"))
+        expect(Datadog::Core::Telemetry::Logger).to receive(:report)
+          .with(error, description: 'Matcher failed')
       end
 
       it { is_expected.to be nil }