diff --git a/hcl2/rules/base.py b/hcl2/rules/base.py
index ce457f45..dacec8b4 100644
--- a/hcl2/rules/base.py
+++ b/hcl2/rules/base.py
@@ -85,8 +85,8 @@ def serialize(
                 attribute_names.add(child.identifier.serialize(options))
                 result.update(child.serialize(options))
                 if options.with_comments:
-                    # collect in-line comments from attribute assignments, expressions etc
                     inline_comments.extend(child.expression.inline_comments())
+                    comments.extend(child.expression.absorbed_comments())
 
             if isinstance(child, NewLineOrCommentRule) and options.with_comments:
                 child_comments = child.to_list()
diff --git a/hcl2/rules/expressions.py b/hcl2/rules/expressions.py
index f29eea5a..057e1ffc 100644
--- a/hcl2/rules/expressions.py
+++ b/hcl2/rules/expressions.py
@@ -242,6 +242,38 @@ def binary_term(self) -> BinaryTermRule:
         """Return the binary term (operator + right-hand operand)."""
         return self._children[1]
 
+    @property
+    def _trailing_nl(self) -> Optional[NewLineOrCommentRule]:
+        """Return the trailing new_line_or_comment child, if present."""
+        child = self._children[2]
+        if isinstance(child, NewLineOrCommentRule):
+            return child
+        return None
+
+    def inline_comments(self):
+        """Collect inline comments, excluding absorbed body-level comments."""
+        trailing = self._trailing_nl
+        result = []
+        for child in self._children:
+            if isinstance(child, NewLineOrCommentRule):
+                # Trailing NL_OR_COMMENT with a leading newline contains
+                # body-level comments absorbed by the grammar, not inline ones.
+                if child is trailing and not child.is_inline:
+                    continue
+                comments = child.to_list()
+                if comments is not None:
+                    result.extend(comments)
+            elif isinstance(child, InlineCommentMixIn):
+                result.extend(child.inline_comments())
+        return result
+
+    def absorbed_comments(self):
+        """Return body-level comments absorbed into the trailing NL_OR_COMMENT."""
+        trailing = self._trailing_nl
+        if trailing is not None and not trailing.is_inline:
+            return trailing.to_list() or []
+        return []
+
     def serialize(
         self, options=SerializationOptions(), context=SerializationContext()
     ) -> Any:
diff --git a/hcl2/rules/whitespace.py b/hcl2/rules/whitespace.py
index 9488a77b..9cb464f7 100644
--- a/hcl2/rules/whitespace.py
+++ b/hcl2/rules/whitespace.py
@@ -26,7 +26,17 @@ def serialize(
         self, options=SerializationOptions(), context=SerializationContext()
     ) -> Any:
         """Serialize to the raw comment/newline string."""
-        return self.token.serialize()
+        return "".join(child.serialize() for child in self._children)
+
+    @property
+    def is_inline(self) -> bool:
+        """True if this comment is on the same line as preceding code.
+
+        A raw string starting with ``\\n`` means the comment sits on its own
+        line (standalone).  One starting with ``#``, ``//``, or ``/*`` is
+        inline — it follows code on the same line.
+        """
+        return not self.serialize().startswith("\n")
 
     def to_list(
         self, options: SerializationOptions = SerializationOptions()
@@ -91,3 +101,11 @@ def inline_comments(self):
                 result.extend(child.inline_comments())
 
         return result
+
+    def absorbed_comments(self):
+        """Return body-level comments absorbed by grammar into this expression.
+
+        Default: empty.  ``BinaryOpRule`` overrides this because its trailing
+        ``new_line_or_comment?`` can swallow the next body-level comment.
+        """
+        return []
diff --git a/test/integration/specialized/comments.json b/test/integration/specialized/comments.json
new file mode 100644
index 00000000..5d7e6ef4
--- /dev/null
+++ b/test/integration/specialized/comments.json
@@ -0,0 +1,57 @@
+{
+  "resource": [
+    {
+      "\"aws_instance\"": {
+        "\"web\"": {
+          "ami": "\"abc-123\"",
+          "instance_type": "\"t2.micro\"",
+          "count": "${1 + 2}",
+          "tags": {
+            "Name": "\"web\"",
+            "Env": "\"prod\""
+          },
+          "enabled": "true",
+          "nested": [
+            {
+              "key": "\"value\"",
+              "__comments__": [
+                {
+                  "value": "comment inside nested block"
+                }
+              ],
+              "__is_block__": true
+            }
+          ],
+          "__comments__": [
+            {
+              "value": "standalone comment inside block"
+            },
+            {
+              "value": "hash standalone comment"
+            },
+            {
+              "value": "absorbed standalone after binary_op"
+            },
+            {
+              "value": "multi-line\n  block comment"
+            }
+          ],
+          "__inline_comments__": [
+            {
+              "value": "comment inside object"
+            },
+            {
+              "value": "inline after value"
+            }
+          ],
+          "__is_block__": true
+        }
+      }
+    }
+  ],
+  "__comments__": [
+    {
+      "value": "top-level standalone comment"
+    }
+  ]
+}
diff --git a/test/integration/specialized/comments.tf b/test/integration/specialized/comments.tf
new file mode 100644
index 00000000..6755f2d3
--- /dev/null
+++ b/test/integration/specialized/comments.tf
@@ -0,0 +1,28 @@
+// top-level standalone comment
+resource "aws_instance" "web" {
+  ami = "abc-123"
+
+  // standalone comment inside block
+  instance_type = "t2.micro"
+
+  # hash standalone comment
+  count = 1 + 2
+  # absorbed standalone after binary_op
+
+  tags = {
+    Name = "web"
+    # comment inside object
+    Env  = "prod" # inline after value
+  }
+
+  /*
+  multi-line
+  block comment
+  */
+  enabled = true
+
+  nested {
+    // comment inside nested block
+    key = "value"
+  }
+}
diff --git a/test/integration/test_specialized.py b/test/integration/test_specialized.py
index 399b486a..60faf194 100644
--- a/test/integration/test_specialized.py
+++ b/test/integration/test_specialized.py
@@ -150,6 +150,86 @@ def test_full_round_trip(self):
         self.assertEqual(reserialized, serialized)
 
 
+class TestCommentSerialization(TestCase):
+    """Test that comments are correctly classified during HCL → JSON serialization.
+
+    Covers:
+    - Standalone comments (// and #) at body level → __comments__
+    - Standalone comments absorbed by binary_op grammar → __comments__
+    - Comments inside expressions (objects) → __inline_comments__
+    - Multi-line block comments → __comments__
+    - Comments in nested blocks
+    - Top-level comments
+    """
+
+    maxDiff = None
+    _OPTIONS = SerializationOptions(with_comments=True)
+
+    def test_comment_classification(self):
+        hcl_path = SPECIAL_DIR / "comments.tf"
+        json_path = SPECIAL_DIR / "comments.json"
+
+        actual = _parse_and_serialize(hcl_path.read_text(), options=self._OPTIONS)
+        expected = json.loads(json_path.read_text())
+
+        self.assertEqual(actual, expected)
+
+    def test_top_level_comments(self):
+        actual = _parse_and_serialize("// file header\nx = 1\n", options=self._OPTIONS)
+        self.assertEqual(actual["__comments__"], [{"value": "file header"}])
+
+    def test_standalone_in_body(self):
+        actual = _parse_and_serialize(
+            'resource "a" "b" {\n  # standalone\n  x = 1\n}\n',
+            options=self._OPTIONS,
+        )
+        block = actual["resource"][0]['"a"']['"b"']
+        self.assertEqual(block["__comments__"], [{"value": "standalone"}])
+        self.assertNotIn("__inline_comments__", block)
+
+    def test_absorbed_after_binary_op(self):
+        actual = _parse_and_serialize(
+            "x {\n  a = 1 + 2\n  # absorbed\n  b = 3\n}\n",
+            options=self._OPTIONS,
+        )
+        block = actual["x"][0]
+        self.assertIn({"value": "absorbed"}, block["__comments__"])
+        self.assertNotIn("__inline_comments__", block)
+
+    def test_inline_after_binary_op(self):
+        actual = _parse_and_serialize(
+            "x {\n  a = 1 + 2 # inline\n  b = 3\n}\n",
+            options=self._OPTIONS,
+        )
+        block = actual["x"][0]
+        self.assertEqual(block["__inline_comments__"], [{"value": "inline"}])
+
+    def test_comment_inside_object(self):
+        actual = _parse_and_serialize(
+            "x {\n  m = {\n    # inside\n    k = 1\n  }\n}\n",
+            options=self._OPTIONS,
+        )
+        block = actual["x"][0]
+        self.assertEqual(block["__inline_comments__"], [{"value": "inside"}])
+        self.assertNotIn("__comments__", block)
+
+    def test_multiline_block_comment(self):
+        actual = _parse_and_serialize(
+            "x {\n  /*\n  multi\n  line\n  */\n  a = 1\n}\n",
+            options=self._OPTIONS,
+        )
+        block = actual["x"][0]
+        self.assertEqual(block["__comments__"], [{"value": "multi\n  line"}])
+
+    def test_no_comments_without_option(self):
+        actual = _parse_and_serialize(
+            "// comment\nx = 1\n",
+            options=SerializationOptions(with_comments=False),
+        )
+        self.assertNotIn("__comments__", actual)
+        self.assertNotIn("__inline_comments__", actual)
+
+
 class TestHeredocs(TestCase):
     """Test heredoc serialization, flattening, restoration, and round-trips.