diff --git a/lib/ddtrace/profiling/ext/cpu.rb b/lib/ddtrace/profiling/ext/cpu.rb
index d0a5d0955b5..7eb7be20b0e 100644
--- a/lib/ddtrace/profiling/ext/cpu.rb
+++ b/lib/ddtrace/profiling/ext/cpu.rb
@@ -5,6 +5,17 @@ module Ext
       module CPU
         FFI_MINIMUM_VERSION = Gem::Version.new('1.0')
 
+        # We cannot apply our CPU extension if a broken rollbar is around because that can cause customer apps to fail
+        # with a SystemStackError: stack level too deep.
+        #
+        # This occurs whenever our extensions to Thread are applied BEFORE rollbar applies its own. This happens
+        # because a loop forms: our extension tries to call Thread#initialize, but it's intercepted by rollbar, which
+        # then tries to call the original Thread#initialize as well, but instead alls our extension, leading to stack
+        # exhaustion.
+        #
+        # See https://github.com/rollbar/rollbar-gem/pull/1018 for more details on the issue
+        ROLLBAR_INCOMPATIBLE_VERSIONS = Gem::Requirement.new('<= 3.1.1')
+
         def self.supported?
           unsupported_reason.nil?
         end
@@ -37,6 +48,10 @@ def self.unsupported_reason
           elsif Gem.loaded_specs['ffi'].version < FFI_MINIMUM_VERSION
             'Your ffi gem dependency is too old; ensure that you have ffi >= 1.0 by ' \
             "adding `gem 'ffi', '~> 1.0'` to your Gemfile or gems.rb file"
+          elsif Gem::Specification.find_all_by_name('rollbar', ROLLBAR_INCOMPATIBLE_VERSIONS).any?
+            'You have an incompatible rollbar gem version installed; ensure that you have rollbar >= 3.1.2 by ' \
+            "adding `gem 'rollbar', '>= 3.1.2'` to your Gemfile or gems.rb file. " \
+            'See https://github.com/rollbar/rollbar-gem/pull/1018 for details.'
           end
         end
       end
diff --git a/lib/ddtrace/profiling/tasks/setup.rb b/lib/ddtrace/profiling/tasks/setup.rb
index af044cd913a..bc8802efaac 100644
--- a/lib/ddtrace/profiling/tasks/setup.rb
+++ b/lib/ddtrace/profiling/tasks/setup.rb
@@ -9,7 +9,6 @@ module Tasks
       # Takes care of loading our extensions/monkey patches and starting up profiler
       class Setup
         def run
-          check_warnings!
           activate_main_extensions
           autostart_profiler
         end
@@ -80,22 +79,6 @@ def autostart_profiler
           log "[DDTRACE] Could not autostart profiling. Cause: #{e.message} Location: #{e.backtrace.first}"
         end
 
-        def check_warnings!
-          warn_if_incompatible_rollbar_gem_detected
-        end
-
-        # See https://github.com/rollbar/rollbar-gem/pull/1018 for details on the incompatibility
-        def warn_if_incompatible_rollbar_gem_detected
-          incompatible_rollbar_versions = Gem::Requirement.new('<= 3.1.1')
-
-          if Gem::Specification.find_all_by_name('rollbar', incompatible_rollbar_versions).any?
-            log "[DDTRACE] Incompatible version of the rollbar gem is installed (#{incompatible_rollbar_versions}). " \
-              'Loading this version of the rollbar gem will disable ddtrace\'s CPU profiling. ' \
-              'Please upgrade to the latest rollbar version. ' \
-              'See https://github.com/rollbar/rollbar-gem/pull/1018 for details.'
-          end
-        end
-
         private
 
         def log(message)
diff --git a/spec/ddtrace/profiling/ext/cpu_spec.rb b/spec/ddtrace/profiling/ext/cpu_spec.rb
index 20ce6b8a9dd..f43cb2ff444 100644
--- a/spec/ddtrace/profiling/ext/cpu_spec.rb
+++ b/spec/ddtrace/profiling/ext/cpu_spec.rb
@@ -74,7 +74,29 @@
                 include_context 'loaded gems',
                                 ffi: described_class::FFI_MINIMUM_VERSION
 
-                it { is_expected.to be nil }
+                let(:last_version_of_rollbar_affected) { '3.1.1' }
+
+                context 'when incompatible rollbar gem is installed' do
+                  before do
+                    expect(Gem::Specification)
+                      .to receive(:find_all_by_name)
+                      .with('rollbar', Gem::Requirement.new("<= #{last_version_of_rollbar_affected}"))
+                      .and_return([instance_double(Gem::Specification), instance_double(Gem::Specification)])
+                  end
+
+                  it { is_expected.to include 'rollbar >= 3.1.2'}
+                end
+
+                context 'when compatible rollbar gem is installed or no version at all is installed' do
+                  before do
+                    expect(Gem::Specification)
+                      .to receive(:find_all_by_name)
+                      .with('rollbar', Gem::Requirement.new("<= #{last_version_of_rollbar_affected}"))
+                      .and_return([]) # Because we search with a <= requirement, not installed/compatible version installed both lead to empty return here
+                  end
+
+                  it { is_expected.to be nil }
+                end
               end
             end
           end
@@ -89,7 +111,7 @@
     before { stub_const('Thread', ::Thread.dup) }
 
     context 'when native CPU time is supported' do
-      before { skip 'CPU profiling not supported' unless described_class.supported? }
+      before { skip 'CPU profiling not supported on current platform' unless described_class.supported? }
 
       it 'adds Thread extensions' do
         apply!
diff --git a/spec/ddtrace/profiling/tasks/setup_spec.rb b/spec/ddtrace/profiling/tasks/setup_spec.rb
index 5d77dcf5d5c..0d80f745931 100644
--- a/spec/ddtrace/profiling/tasks/setup_spec.rb
+++ b/spec/ddtrace/profiling/tasks/setup_spec.rb
@@ -12,7 +12,6 @@
     subject(:run) { task.run }
 
     it do
-      expect(task).to receive(:check_warnings!).ordered
       expect(task).to receive(:activate_main_extensions).ordered
       expect(task).to receive(:autostart_profiler).ordered
       run
@@ -347,63 +346,4 @@
       end
     end
   end
-
-  describe '#check_warnings!' do
-    subject(:check_warnings!) { task.check_warnings! }
-
-    it do
-      expect(task).to receive(:warn_if_incompatible_rollbar_gem_detected)
-
-      check_warnings!
-    end
-  end
-
-  describe '#warn_if_incompatible_rollbar_gem_detected' do
-    subject(:warn_if_incompatible_rollbar_gem_detected) { task.warn_if_incompatible_rollbar_gem_detected }
-
-    let(:last_version_of_rollbar_affected) { '3.1.1' }
-
-    before do
-      # Simulate the result of the gem apis, so that we can check different combinations of having or not having the
-      # rollbar gem and affected versions
-      expect(Gem::Specification)
-        .to receive(:find_all_by_name)
-        .with('rollbar', Gem::Requirement.new("<= #{last_version_of_rollbar_affected}"))
-        .and_return(rollbar_versions_found)
-    end
-
-    context 'when rollbar gem is not installed' do
-      let(:rollbar_versions_found) { [] }
-
-      it 'does not display a warning to STDOUT' do
-        expect(STDOUT).to_not receive(:puts)
-
-        warn_if_incompatible_rollbar_gem_detected
-      end
-    end
-
-    context 'when compatible version of rollbar gem is installed' do
-      # same as "no gem installed" because we use a version requirement when
-      # calling find_all_by_name, so only incompatible versions get returned
-      let(:rollbar_versions_found) { [] }
-
-      it 'does not display a warning to STDOUT' do
-        expect(STDOUT).to_not receive(:puts)
-
-        warn_if_incompatible_rollbar_gem_detected
-      end
-    end
-
-    context 'when incompatible version of rollbar gem is installed' do
-      let(:rollbar_versions_found) { [instance_double(Gem::Specification), instance_double(Gem::Specification)] }
-
-      it 'displays a warning to STDOUT' do
-        expect(STDOUT).to receive(:puts) do |message|
-          expect(message).to include('Incompatible version of the rollbar')
-        end
-
-        warn_if_incompatible_rollbar_gem_detected
-      end
-    end
-  end
 end