diff --git a/spec/ddcov/calculator_with_symlinks/calculator.rb b/spec/ddcov/calculator_with_symlinks/calculator.rb
new file mode 100644
index 00000000..9f1cbc00
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/calculator.rb
@@ -0,0 +1,28 @@
+# frozen_string_literal: true
+
+require_relative "vendor/gems/operations/operations"
+
+class Calculator
+  def initialize
+    @adder = Add.new
+    @subtractor = Subtract.new
+    @multiplier = Multiply.new
+    @divider = Divide.new
+  end
+
+  def add(a, b)
+    @adder.call(a, b)
+  end
+
+  def subtract(a, b)
+    @subtractor.call(a, b)
+  end
+
+  def multiply(a, b)
+    @multiplier.call(a, b)
+  end
+
+  def divide(a, b)
+    @divider.call(a, b)
+  end
+end
diff --git a/spec/ddcov/calculator_with_symlinks/operations/add.rb b/spec/ddcov/calculator_with_symlinks/operations/add.rb
new file mode 100644
index 00000000..ad4ca3a1
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/operations/add.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class Add
+  def call(a, b)
+    a + b
+  end
+end
diff --git a/spec/ddcov/calculator_with_symlinks/operations/divide.rb b/spec/ddcov/calculator_with_symlinks/operations/divide.rb
new file mode 100644
index 00000000..178b9a83
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/operations/divide.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+require_relative "helpers/calculator_logger"
+
+class Divide
+  prepend CalculatorLogger
+
+  def call(a, b)
+    a / b
+  end
+end
diff --git a/spec/ddcov/calculator_with_symlinks/operations/helpers/calculator_logger.rb b/spec/ddcov/calculator_with_symlinks/operations/helpers/calculator_logger.rb
new file mode 100644
index 00000000..e46399b8
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/operations/helpers/calculator_logger.rb
@@ -0,0 +1,12 @@
+# frozen_string_literal: true
+
+module CalculatorLogger
+  def call(a, b)
+    res = super
+
+    @log ||= []
+    @log << "operation performed"
+
+    res
+  end
+end
diff --git a/spec/ddcov/calculator_with_symlinks/operations/multiply.rb b/spec/ddcov/calculator_with_symlinks/operations/multiply.rb
new file mode 100644
index 00000000..0290d969
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/operations/multiply.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class Multiply
+  def call(a, b)
+    a * b
+  end
+end
diff --git a/spec/ddcov/calculator_with_symlinks/operations/operations.rb b/spec/ddcov/calculator_with_symlinks/operations/operations.rb
new file mode 100644
index 00000000..7fb3b210
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/operations/operations.rb
@@ -0,0 +1,4 @@
+require_relative "add"
+require_relative "divide"
+require_relative "multiply"
+require_relative "subtract"
diff --git a/spec/ddcov/calculator_with_symlinks/operations/subtract.rb b/spec/ddcov/calculator_with_symlinks/operations/subtract.rb
new file mode 100644
index 00000000..da667953
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/operations/subtract.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class Subtract
+  def call(a, b)
+    a - b
+  end
+end
diff --git a/spec/ddcov/calculator_with_symlinks/vendor/gems/operations b/spec/ddcov/calculator_with_symlinks/vendor/gems/operations
new file mode 120000
index 00000000..accd45a8
--- /dev/null
+++ b/spec/ddcov/calculator_with_symlinks/vendor/gems/operations
@@ -0,0 +1 @@
+/Users/andrey.marchenko/p/datadog-ci-rb/spec/ddcov/calculator_with_symlinks/operations
\ No newline at end of file
diff --git a/spec/ddcov/ddcov_with_symlinks_spec.rb b/spec/ddcov/ddcov_with_symlinks_spec.rb
new file mode 100644
index 00000000..915f438c
--- /dev/null
+++ b/spec/ddcov/ddcov_with_symlinks_spec.rb
@@ -0,0 +1,37 @@
+# frozen_string_literal: true
+
+require "datadog_cov.#{RUBY_VERSION}_#{RUBY_PLATFORM}"
+
+require_relative "calculator_with_symlinks/calculator"
+
+RSpec.describe Datadog::CI::ITR::Coverage::DDCov do
+  def absolute_path(path)
+    File.expand_path(File.join(__dir__, path))
+  end
+
+  subject { described_class.new(root: root) }
+
+  describe "code coverage collection" do
+    let!(:calculator) { Calculator.new }
+
+    context "when root is the calculator project dir" do
+      let(:root) { absolute_path("calculator_with_symlinks") }
+
+      it "collects code coverage including Calculator and operations" do
+        subject.start
+
+        expect(calculator.add(1, 2)).to eq(3)
+        expect(calculator.subtract(1, 2)).to eq(-1)
+
+        coverage = subject.stop
+
+        expect(coverage.size).to eq(3)
+        expect(coverage.keys).to include(
+          absolute_path("calculator_with_symlinks/calculator.rb"),
+          absolute_path("calculator_with_symlinks/operations/add.rb"),
+          absolute_path("calculator_with_symlinks/operations/subtract.rb")
+        )
+      end
+    end
+  end
+end