diff --git a/cspell.json b/cspell.json
index 2b900a1..9342020 100644
--- a/cspell.json
+++ b/cspell.json
@@ -4,14 +4,15 @@
     "dictionaryDefinitions": [],
     "dictionaries": [],
     "words": [
-        "Rubrik",
-        "PKCS",
-        "Tempfile",
-        "rubygems",
-        "ETSI",
+        "Annots",
         "codebases",
         "devcontainer",
-        "simplecov"
+        "ETSI",
+        "PKCS",
+        "Rubrik",
+        "rubygems",
+        "simplecov",
+        "Tempfile"
     ],
     "ignoreWords": [],
     "import": []
diff --git a/lib/rubrik/document.rb b/lib/rubrik/document.rb
index e629bd1..c7ca32c 100644
--- a/lib/rubrik/document.rb
+++ b/lib/rubrik/document.rb
@@ -76,10 +76,20 @@ def add_signature_field
         }
       }
 
-      modified_page = objects.fetch(first_page_reference).dup
-      (modified_page[:Annots] ||= []) << signature_field_id
+      first_page = objects.fetch(first_page_reference)
+      annots = first_page[:Annots]
 
-      modified_objects << {id: first_page_reference, value: modified_page}
+      if annots.is_a?(PDF::Reader::Reference)
+        new_annots = objects.fetch(annots).dup
+        new_annots << signature_field_id
+
+        modified_objects << {id: annots, value: new_annots}
+      else
+        new_first_page = first_page.dup
+        (new_first_page[:Annots] ||= []) << signature_field_id
+
+        modified_objects << {id: first_page_reference, value: new_first_page}
+      end
 
       (interactive_form[:Fields] ||= []) << signature_field_id
 
diff --git a/test/rubrik/document_test.rb b/test/rubrik/document_test.rb
index 032886d..6bdcb4b 100644
--- a/test/rubrik/document_test.rb
+++ b/test/rubrik/document_test.rb
@@ -18,7 +18,7 @@ def test_initialize_document_without_interactive_form
       assert_equal(6, document.last_object_id)
       assert_kind_of(PDF::Reader::ObjectHash, document.objects)
 
-      acro_form = document.modified_objects.find { |obj| obj.dig(:value, :Type) == :Catalog }
+      acro_form = document.modified_objects.find { |obj| obj.is_a?(Hash) && obj.dig(:value, :Type) == :Catalog }
       acro_form_reference = T.must(acro_form).dig(:value, :AcroForm)
       assert_pattern do
         document.modified_objects => [*, {id: ^acro_form_reference, value: {Fields: [], SigFlags: 3}}, *]
@@ -62,7 +62,7 @@ def test_add_signature_field
       assert_equal(3, number_of_added_objects)
 
       assert_pattern do
-        signature_value = document.modified_objects.find { _1[:id] == result }
+        signature_value = document.modified_objects.find { _1.is_a?(Hash) && _1[:id] == result }
         signature_value => {id: ^result,
           value: {
             Type: :Sig,
@@ -74,7 +74,7 @@ def test_add_signature_field
         }
       end
 
-      signature_field = document.modified_objects.find { _1.dig(:value, :FT) == :Sig }
+      signature_field = document.modified_objects.find { _1.is_a?(Hash) && _1.dig(:value, :FT) == :Sig }
       assert_pattern do
         first_page_reference = document.objects.page_references[0]
         signature_field => {
@@ -93,12 +93,66 @@ def test_add_signature_field
 
       signature_field_id = T.must(signature_field)[:id]
 
-      first_page = document.modified_objects.find { _1.dig(:value, :Type) == :Page }
+      first_page = document.modified_objects.find { _1.is_a?(Hash) && _1.dig(:value, :Type) == :Page }
       assert_pattern { first_page => {value: {Annots: [*, ^signature_field_id, *]}}}
 
       assert_pattern { document.send(:interactive_form) => {Fields: [*, ^signature_field_id, *]} }
     ensure
       input&.close
     end
+
+    def test_add_signature_field_with_indirect_annots
+      # Arrange
+      input = File.open(SupportPDF["indirect_annots"], "rb")
+      document = Document.new(input)
+      initial_number_of_objects = document.modified_objects.size
+
+      # Act
+      result = document.add_signature_field
+
+      # Assert
+      number_of_added_objects = document.modified_objects.size - initial_number_of_objects
+      assert_equal(3, number_of_added_objects)
+
+      assert_pattern do
+        signature_value = document.modified_objects.find { _1.is_a?(Hash) && _1[:id] == result }
+        signature_value => {id: ^result,
+          value: {
+            Type: :Sig,
+            Filter: :"Adobe.PPKLite",
+            SubFilter: :"adbe.pkcs7.detached",
+            Contents: Document::CONTENTS_PLACEHOLDER,
+            ByteRange: Document::BYTE_RANGE_PLACEHOLDER
+          }
+        }
+      end
+
+      signature_field = document.modified_objects.find { _1.is_a?(Hash) && _1.dig(:value, :FT) == :Sig }
+      assert_pattern do
+        first_page_reference = document.objects.page_references[0]
+        signature_field => {
+          id: PDF::Reader::Reference,
+          value: {
+            T: /Signature-\w{4}/,
+            V: ^result,
+            Type: :Annot,
+            Subtype: :Widget,
+            Rect: [0, 0, 0, 0],
+            F: 4,
+            P: ^first_page_reference
+          }
+        }
+      end
+
+      signature_field_id = T.must(signature_field)[:id]
+
+      assert_pattern do
+        document.modified_objects => [*, {id: PDF::Reader::Reference, value: [signature_field_id]} , *]
+      end
+
+      assert_pattern { document.send(:interactive_form) => {Fields: [*, ^signature_field_id, *]} }
+    ensure
+      input&.close
+    end
   end
 end
diff --git a/test/pkcs7_signature_test.rb b/test/rubrik/pkcs7_signature_test.rb
similarity index 100%
rename from test/pkcs7_signature_test.rb
rename to test/rubrik/pkcs7_signature_test.rb
diff --git a/test/rubrik/sign_test.rb b/test/rubrik/sign_test.rb
index 8eff1bb..c6217be 100644
--- a/test/rubrik/sign_test.rb
+++ b/test/rubrik/sign_test.rb
@@ -76,5 +76,44 @@ def test_document_without_interactive_form
       input_pdf&.close
       expected_output&.close
     end
+
+    def test_document_with_indirect_annots
+      # Arrange
+      input_pdf = File.open(SupportPDF["indirect_annots"], "rb")
+      # FACT: the output file is opened with only write permission and should be later reopened to rw.
+      output_pdf = File.open(SupportPDF["indirect_annots_temp"], "wb")
+      certificate_file = File.open("test/support/demo_cert.pem", "rb")
+
+      private_key = OpenSSL::PKey::RSA.new(certificate_file, "")
+      certificate_file.rewind
+      certificate = OpenSSL::X509::Certificate.new(certificate_file)
+
+      # Act
+      Sign.call(input_pdf, output_pdf, private_key:, certificate:)
+
+      # Assert
+      expected_output = File.open(SupportPDF["indirect_annots.expected"], "rb")
+
+      expected_output.readlines.zip(output_pdf.readlines).each do |(expected_line, actual_line)|
+        # We can't verify the signature because it changes on every run
+        if actual_line&.match?("/Type /Sig")
+          actual_line.sub!(/<[a-f0-9]+>/, "")
+          expected_line.sub!(/<[a-f0-9]+>/, "")
+        # The signature field name is also random
+        elsif actual_line&.match?(/Signature-[a-f0-9]{4}/)
+          actual_line.sub!(/Signature-[a-f0-9]{4}/, "")
+          expected_line.sub!(/Signature-[a-f0-9]{4}/, "")
+        end
+
+        assert_equal(expected_line, actual_line)
+      end
+    ensure
+      certificate_file&.close
+      input_pdf&.close
+      expected_output&.close
+
+      output_pdf&.close
+      File.delete(output_pdf.path) if output_pdf
+    end
   end
 end
diff --git a/test/support/indirect_annots.expected.pdf b/test/support/indirect_annots.expected.pdf
new file mode 100644
index 0000000..a4deb76
Binary files /dev/null and b/test/support/indirect_annots.expected.pdf differ
diff --git a/test/support/indirect_annots.pdf b/test/support/indirect_annots.pdf
new file mode 100644
index 0000000..924186e
Binary files /dev/null and b/test/support/indirect_annots.pdf differ