diff --git a/lib/datadog/core/remote/client.rb b/lib/datadog/core/remote/client.rb
index 911011515fa..8c5c2767245 100644
--- a/lib/datadog/core/remote/client.rb
+++ b/lib/datadog/core/remote/client.rb
@@ -10,6 +10,7 @@ module Core
     module Remote
       # Client communicates with the agent and sync remote configuration
       class Client
+        class TransportError < StandardError; end
         class SyncError < StandardError; end
 
         attr_reader :transport, :repository, :id, :dispatcher
@@ -107,6 +108,8 @@ def sync
             else
               dispatcher.dispatch(changes, repository)
             end
+          elsif response.internal_error?
+            raise TransportError, response.to_s
           end
         end
         # rubocop:enable Metrics/AbcSize,Metrics/PerceivedComplexity,Metrics/MethodLength,Metrics/CyclomaticComplexity
diff --git a/lib/datadog/core/remote/component.rb b/lib/datadog/core/remote/component.rb
index 34838c8d75f..aea2ed828ca 100644
--- a/lib/datadog/core/remote/component.rb
+++ b/lib/datadog/core/remote/component.rb
@@ -45,6 +45,11 @@ def initialize(settings, capabilities, agent_settings)
                 "remote worker client sync error: #{e.message} location: #{Array(e.backtrace).first}. skipping sync"
               end
             rescue StandardError => e
+              # In case of unexpected errors, reset the negotiation object
+              # given external conditions have changed and the negotiation
+              # negotiation object stores error logging state that should be reset.
+              negotiation = Negotiation.new(settings, agent_settings)
+
               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 f9307dfe041..823d330f5f6 100644
--- a/lib/datadog/core/remote/negotiation.rb
+++ b/lib/datadog/core/remote/negotiation.rb
@@ -12,31 +12,44 @@ def initialize(_settings, agent_settings)
           transport_options[:agent_settings] = agent_settings if agent_settings
 
           @transport_root = Datadog::Core::Transport::HTTP.root(**transport_options.dup)
+          @logged = {}
         end
 
         def endpoint?(path)
           res = @transport_root.send_info
 
           if res.internal_error? && network_error?(res.error)
-            Datadog.logger.error { "agent unreachable: cannot negotiate #{path}" }
+            unless @logged[:agent_unreachable]
+              Datadog.logger.error { "agent unreachable: cannot negotiate #{path}" }
+              @logged[:agent_unreachable] = true
+            end
 
             return false
           end
 
           if res.not_found?
-            Datadog.logger.error { "agent reachable but has no /info endpoint: cannot negotiate #{path}" }
+            unless @logged[:no_info_endpoint]
+              Datadog.logger.error { "agent reachable but has no /info endpoint: cannot negotiate #{path}" }
+              @logged[:no_info_endpoint] = true
+            end
 
             return false
           end
 
           unless res.ok?
-            Datadog.logger.error { "agent reachable but unexpected response: cannot negotiate #{path}" }
+            unless @logged[:unexpected_response]
+              Datadog.logger.error { "agent reachable but unexpected response: cannot negotiate #{path}" }
+              @logged[:unexpected_response] = true
+            end
 
             return false
           end
 
           unless res.endpoints.include?(path)
-            Datadog.logger.error { "agent reachable but does not report #{path}" }
+            unless @logged[:no_config_endpoint]
+              Datadog.logger.error { "agent reachable but does not report #{path}" }
+              @logged[:no_config_endpoint] = true
+            end
 
             return false
           end
diff --git a/lib/datadog/core/transport/http/client.rb b/lib/datadog/core/transport/http/client.rb
index 09437936060..89d1325daa5 100644
--- a/lib/datadog/core/transport/http/client.rb
+++ b/lib/datadog/core/transport/http/client.rb
@@ -30,7 +30,7 @@ def send_request(request, &block)
               "Internal error during #{self.class.name} request. Cause: #{e.class.name} #{e.message} " \
               "Location: #{Array(e.backtrace).first}"
 
-            Datadog.logger.error(message)
+            Datadog.logger.debug(message)
 
             Datadog::Transport::InternalErrorResponse.new(e)
           end
diff --git a/sig/datadog/core/remote/client.rbs b/sig/datadog/core/remote/client.rbs
index 1bcdf76d7bf..0521f3bb25b 100644
--- a/sig/datadog/core/remote/client.rbs
+++ b/sig/datadog/core/remote/client.rbs
@@ -2,6 +2,9 @@ module Datadog
   module Core
     module Remote
       class Client
+        class TransportError < StandardError
+        end
+
         class SyncError < StandardError
         end
 
diff --git a/sig/datadog/core/remote/negotiation.rbs b/sig/datadog/core/remote/negotiation.rbs
index d892890f040..126cfc398de 100644
--- a/sig/datadog/core/remote/negotiation.rbs
+++ b/sig/datadog/core/remote/negotiation.rbs
@@ -3,6 +3,7 @@ module Datadog
     module Remote
       class Negotiation
         @transport_root: Datadog::Core::Transport::Negotiation::Transport
+        @logged: ::Hash[::Symbol, bool]
 
         def initialize: (Datadog::Core::Configuration::Settings _settings, Datadog::Core::Configuration::AgentSettingsResolver::AgentSettings agent_settings) -> void
 
diff --git a/spec/datadog/core/remote/client_spec.rb b/spec/datadog/core/remote/client_spec.rb
index 830f66d911e..1db669f53a9 100644
--- a/spec/datadog/core/remote/client_spec.rb
+++ b/spec/datadog/core/remote/client_spec.rb
@@ -12,7 +12,6 @@
       allow(http_request).to receive(:body=)
       allow(request_class).to receive(:new).and_return(http_request)
 
-      http_connection = instance_double(::Net::HTTP)
       allow(::Net::HTTP).to receive(:new).and_return(http_connection)
 
       allow(http_connection).to receive(:open_timeout=)
@@ -37,6 +36,7 @@
     end
   end
 
+  let(:http_connection) { instance_double(::Net::HTTP) }
   let(:transport) { Datadog::Core::Transport::HTTP.v7(&proc { |_client| }) }
   let(:roots) do
     [
@@ -458,6 +458,14 @@
           end
         end
       end
+
+      context 'with a network error' do
+        it 'raises a transport error' do
+          expect(http_connection).to receive(:request).and_raise(IOError)
+
+          expect { client.sync }.to raise_error(Datadog::Core::Remote::Client::TransportError)
+        end
+      end
     end
 
     describe '#payload' do
diff --git a/spec/datadog/core/remote/component_spec.rb b/spec/datadog/core/remote/component_spec.rb
index d0ff1dbc98f..ce99f0a7f63 100644
--- a/spec/datadog/core/remote/component_spec.rb
+++ b/spec/datadog/core/remote/component_spec.rb
@@ -61,7 +61,7 @@
       before do
         expect(Datadog::Core::Transport::HTTP).to receive(:v7).and_return(transport_v7)
         expect(Datadog::Core::Remote::Client).to receive(:new).and_return(client)
-        expect(Datadog::Core::Remote::Negotiation).to receive(:new).and_return(negotiation)
+        allow(Datadog::Core::Remote::Negotiation).to receive(:new).and_return(negotiation)
 
         expect(worker).to receive(:start).and_call_original
         expect(worker).to receive(:stop).and_call_original
@@ -118,6 +118,14 @@
 
             expect(component.client.object_id).to eql(second_client.object_id)
           end
+
+          it 'resets the negotiation object' do
+            allow(Datadog::Core::Remote::Client).to receive(:new).and_return(second_client)
+
+            component.barrier(:once)
+
+            expect(Datadog::Core::Remote::Negotiation).to have_received(:new).twice
+          end
         end
 
         context 'Client::SyncError' do
diff --git a/spec/datadog/core/remote/negotiation_spec.rb b/spec/datadog/core/remote/negotiation_spec.rb
index 556bdc2b252..ed1c503e38a 100644
--- a/spec/datadog/core/remote/negotiation_spec.rb
+++ b/spec/datadog/core/remote/negotiation_spec.rb
@@ -34,7 +34,8 @@
   describe '#endpoint?' do
     include_context 'HTTP connection stub'
 
-    subject(:negotiation) { described_class.new(settings, agent_settings) }
+    subject(:endpoint?) { negotiation.endpoint?('/foo') }
+    let(:negotiation) { described_class.new(settings, agent_settings) }
 
     context 'when /info exists' do
       let(:response_code) { 200 }
@@ -50,7 +51,7 @@
       it do
         expect(Datadog.logger).to_not receive(:error)
 
-        expect(negotiation.endpoint?('/foo')).to be true
+        expect(endpoint?).to be true
       end
 
       it do
@@ -68,7 +69,14 @@
         expect(Datadog.logger).to receive(:error).and_return(nil)
       end
 
-      it { expect(negotiation.endpoint?('/foo')).to be false }
+      it { expect(endpoint?).to be false }
+
+      context 'on repeated errors' do
+        it 'only logs once' do
+          negotiation.endpoint?('/foo')
+          negotiation.endpoint?('/foo')
+        end
+      end
     end
 
     context 'when agent rejects request' do
@@ -79,7 +87,14 @@
         expect(Datadog.logger).to receive(:error).and_return(nil)
       end
 
-      it { expect(negotiation.endpoint?('/foo')).to be false }
+      it { expect(endpoint?).to be false }
+
+      context 'on repeated errors' do
+        it 'only logs once' do
+          negotiation.endpoint?('/foo')
+          negotiation.endpoint?('/foo')
+        end
+      end
     end
 
     context 'when agent is in error' do
@@ -90,7 +105,14 @@
         expect(Datadog.logger).to receive(:error).and_return(nil)
       end
 
-      it { expect(negotiation.endpoint?('/foo')).to be false }
+      it { expect(endpoint?).to be false }
+
+      context 'on repeated errors' do
+        it 'only logs once' do
+          negotiation.endpoint?('/foo')
+          negotiation.endpoint?('/foo')
+        end
+      end
     end
 
     context 'when agent causes an error' do
@@ -100,20 +122,34 @@
       end
 
       before do
-        expect(Datadog.logger).to receive(:error).twice.and_return(nil)
+        expect(Datadog.logger).to receive(:error).and_return(nil)
       end
 
-      it { expect(negotiation.endpoint?('/foo')).to be false }
+      it { expect(endpoint?).to be false }
+
+      context 'on repeated errors' do
+        it 'only logs once' do
+          negotiation.endpoint?('/foo')
+          negotiation.endpoint?('/foo')
+        end
+      end
     end
 
     context 'when agent is unreachable' do
       let(:request_exception) { Errno::ECONNREFUSED.new }
 
       before do
-        expect(Datadog.logger).to receive(:error).twice.and_return(nil)
+        expect(Datadog.logger).to receive(:error).and_return(nil)
       end
 
-      it { expect(negotiation.endpoint?('/foo')).to be false }
+      it { expect(endpoint?).to be false }
+
+      context 'on repeated errors' do
+        it 'only logs once' do
+          negotiation.endpoint?('/foo')
+          negotiation.endpoint?('/foo')
+        end
+      end
     end
   end
 end
diff --git a/spec/datadog/core/transport/http_spec.rb b/spec/datadog/core/transport/http_spec.rb
index e89cbd64037..f3b645fbf32 100644
--- a/spec/datadog/core/transport/http_spec.rb
+++ b/spec/datadog/core/transport/http_spec.rb
@@ -18,7 +18,6 @@
       allow(http_request).to receive(:body=)
       allow(request_class).to receive(:new).and_return(http_request)
 
-      http_connection = instance_double(::Net::HTTP)
       allow(::Net::HTTP).to receive(:new).and_return(http_connection)
 
       allow(http_connection).to receive(:open_timeout=)
@@ -32,6 +31,8 @@
     end
   end
 
+  let(:http_connection) { instance_double(::Net::HTTP) }
+
   describe '.root' do
     subject(:transport) { described_class.root(&client_options) }
 
@@ -199,6 +200,16 @@
       it { is_expected.to have_attributes(:roots => be_a(Array)) }
       it { is_expected.to have_attributes(:targets => be_a(Hash)) }
       it { is_expected.to have_attributes(:target_files => be_a(Array)) }
+
+      context 'with a network error' do
+        it 'raises a transport error' do
+          expect(http_connection).to receive(:request).and_raise(IOError)
+
+          expect(Datadog.logger).to receive(:debug).with(/IOError/)
+
+          expect(response).to have_attributes(internal_error?: true)
+        end
+      end
     end
   end
 end