diff --git a/lib/src/ast/css/comment.dart b/lib/src/ast/css/comment.dart
index 04c8b8ebd..4724a83b2 100644
--- a/lib/src/ast/css/comment.dart
+++ b/lib/src/ast/css/comment.dart
@@ -16,9 +16,5 @@ abstract class CssComment extends CssNode {
   /// compressed mode.
   bool get isPreserved;
 
-  /// Whether this comment follows non-comment text on a line and should remain
-  /// attached to that non-comment text when being serialized.
-  bool get isTrailing;
-
   T accept<T>(CssVisitor<T> visitor) => visitor.visitCssComment(this);
 }
diff --git a/lib/src/ast/css/modifiable/comment.dart b/lib/src/ast/css/modifiable/comment.dart
index a6b7749bd..40e7838c7 100644
--- a/lib/src/ast/css/modifiable/comment.dart
+++ b/lib/src/ast/css/modifiable/comment.dart
@@ -13,12 +13,10 @@ import 'node.dart';
 class ModifiableCssComment extends ModifiableCssNode implements CssComment {
   final String text;
   final FileSpan span;
-  final bool _isTrailing;
 
   bool get isPreserved => text.codeUnitAt(2) == $exclamation;
-  bool get isTrailing => _isTrailing;
 
-  ModifiableCssComment(this.text, this.span, this._isTrailing);
+  ModifiableCssComment(this.text, this.span);
 
   T accept<T>(ModifiableCssVisitor<T> visitor) => visitor.visitCssComment(this);
 }
diff --git a/lib/src/ast/sass/statement/loud_comment.dart b/lib/src/ast/sass/statement/loud_comment.dart
index d9443f1b3..41e824645 100644
--- a/lib/src/ast/sass/statement/loud_comment.dart
+++ b/lib/src/ast/sass/statement/loud_comment.dart
@@ -15,11 +15,7 @@ class LoudComment implements Statement {
 
   FileSpan get span => text.span;
 
-  /// Whether this comment follows non-comment text on a line and should remain
-  /// attached to that non-comment text when being serialized.
-  final bool isTrailing;
-
-  LoudComment(this.text, this.isTrailing);
+  LoudComment(this.text);
 
   T accept<T>(StatementVisitor<T> visitor) => visitor.visitLoudComment(this);
 
diff --git a/lib/src/parse/sass.dart b/lib/src/parse/sass.dart
index 0a4d93a90..8bc81ce2c 100644
--- a/lib/src/parse/sass.dart
+++ b/lib/src/parse/sass.dart
@@ -9,7 +9,6 @@ import '../ast/sass.dart';
 import '../interpolation_buffer.dart';
 import '../logger.dart';
 import '../util/character.dart';
-import '../value.dart';
 import 'stylesheet.dart';
 
 /// A parser for the indented syntax.
@@ -99,21 +98,9 @@ class SassParser extends StylesheetParser {
       scanner.readChar();
       next = scanner.peekChar();
     }
-    var url = scanner.substring(start.position);
-    var span = scanner.spanFrom(start);
-
-    if (isPlainImportUrl(url)) {
-      // Serialize [url] as a Sass string because [StaticImport] expects it to
-      // include quotes.
-      return StaticImport(
-          Interpolation([SassString(url).toString()], span), span);
-    } else {
-      try {
-        return DynamicImport(parseImportUrl(url), span);
-      } on FormatException catch (innerError) {
-        error("Invalid URL: ${innerError.message}", span);
-      }
-    }
+
+    return DynamicImport(parseImportUrl(scanner.substring(start.position)),
+        scanner.spanFrom(start));
   }
 
   bool scanElse(int ifIndentation) {
@@ -306,8 +293,7 @@ class SassParser extends StylesheetParser {
     }
     if (!buffer.trailingString.trimRight().endsWith("*/")) buffer.write(" */");
 
-    // The sass syntax does not support trailing loud comments ==> isTrailing = false.
-    return LoudComment(buffer.interpolation(scanner.spanFrom(start)), false);
+    return LoudComment(buffer.interpolation(scanner.spanFrom(start)));
   }
 
   void whitespace() {
diff --git a/lib/src/parse/scss.dart b/lib/src/parse/scss.dart
index 8dd7e0320..aec633d57 100644
--- a/lib/src/parse/scss.dart
+++ b/lib/src/parse/scss.dart
@@ -61,8 +61,8 @@ class ScssParser extends StylesheetParser {
 
   List<Statement> children(Statement child()) {
     scanner.expectChar($lbrace);
+    whitespaceWithoutComments();
     var children = <Statement>[];
-    _whitespaceAndOptionalTrailingLoudComment(children);
     while (true) {
       switch (scanner.peekChar()) {
         case $dollar:
@@ -76,7 +76,7 @@ class ScssParser extends StylesheetParser {
               whitespaceWithoutComments();
               break;
             case $asterisk:
-              children.add(_loudComment(/* isTrailing= */ false));
+              children.add(_loudComment());
               whitespaceWithoutComments();
               break;
             default:
@@ -87,7 +87,7 @@ class ScssParser extends StylesheetParser {
 
         case $semicolon:
           scanner.readChar();
-          _whitespaceAndOptionalTrailingLoudComment(children);
+          whitespaceWithoutComments();
           break;
 
         case $rbrace:
@@ -103,7 +103,7 @@ class ScssParser extends StylesheetParser {
 
   List<Statement> statements(Statement statement()) {
     var statements = <Statement>[];
-    _whitespaceAndOptionalTrailingLoudComment(statements);
+    whitespaceWithoutComments();
     while (!scanner.isDone) {
       switch (scanner.peekChar()) {
         case $dollar:
@@ -117,7 +117,7 @@ class ScssParser extends StylesheetParser {
               whitespaceWithoutComments();
               break;
             case $asterisk:
-              statements.add(_loudComment(/* isTrailing= */ false));
+              statements.add(_loudComment());
               whitespaceWithoutComments();
               break;
             default:
@@ -129,7 +129,7 @@ class ScssParser extends StylesheetParser {
 
         case $semicolon:
           scanner.readChar();
-          _whitespaceAndOptionalTrailingLoudComment(statements);
+          whitespaceWithoutComments();
           break;
 
         default:
@@ -163,7 +163,7 @@ class ScssParser extends StylesheetParser {
   }
 
   /// Consumes a statement-level loud comment block.
-  LoudComment _loudComment(bool isTrailing) {
+  LoudComment _loudComment() {
     var start = scanner.state;
     scanner.expect("/*");
     var buffer = InterpolationBuffer()..write("/*");
@@ -182,8 +182,7 @@ class ScssParser extends StylesheetParser {
           if (scanner.peekChar() != $slash) break;
 
           buffer.writeCharCode(scanner.readChar());
-          return LoudComment(
-              buffer.interpolation(scanner.spanFrom(start)), isTrailing);
+          return LoudComment(buffer.interpolation(scanner.spanFrom(start)));
 
         case $cr:
           scanner.readChar();
@@ -201,26 +200,4 @@ class ScssParser extends StylesheetParser {
       }
     }
   }
-
-  /// Consumes whitespace and optionally a trailing loud comment, adding the
-  /// trailing loud comment to [statements] if consumed.
-  ///
-  /// A trailing loud comment is only possible if the initially consumed
-  /// whitespace lacks any newlines.  If that's the case and a loud comment
-  /// immediately follows, the loud comment will also be consumed.
-  void _whitespaceAndOptionalTrailingLoudComment(List<Statement> statements) {
-    bool sawAnyNewlines = whitespaceWithoutComments();
-    if (_peekForStartOfLoudComment()) {
-      bool isTrailing = !sawAnyNewlines;
-      statements.add(_loudComment(isTrailing));
-      whitespaceWithoutComments();
-    }
-  }
-
-  /// Returns whether the scanner is pointing at the start of a loud comment.
-  bool _peekForStartOfLoudComment() {
-    return !scanner.isDone &&
-        scanner.peekChar() == $slash &&
-        scanner.peekChar(1) == $asterisk;
-  }
 }
diff --git a/lib/src/visitor/async_evaluate.dart b/lib/src/visitor/async_evaluate.dart
index edc2d02f1..2f5cb2e31 100644
--- a/lib/src/visitor/async_evaluate.dart
+++ b/lib/src/visitor/async_evaluate.dart
@@ -1500,7 +1500,7 @@ class _EvaluateVisitor
     }
 
     _parent.addChild(ModifiableCssComment(
-        await _performInterpolation(node.text), node.span, node.isTrailing));
+        await _performInterpolation(node.text), node.span));
     return null;
   }
 
@@ -2424,8 +2424,7 @@ class _EvaluateVisitor
       _endOfImports++;
     }
 
-    _parent
-        .addChild(ModifiableCssComment(node.text, node.span, node.isTrailing));
+    _parent.addChild(ModifiableCssComment(node.text, node.span));
   }
 
   Future<void> visitCssDeclaration(CssDeclaration node) async {
diff --git a/lib/src/visitor/clone_css.dart b/lib/src/visitor/clone_css.dart
index f317859d4..c5d9f855f 100644
--- a/lib/src/visitor/clone_css.dart
+++ b/lib/src/visitor/clone_css.dart
@@ -37,7 +37,7 @@ class _CloneCssVisitor implements CssVisitor<ModifiableCssNode> {
   }
 
   ModifiableCssComment visitCssComment(CssComment node) =>
-      ModifiableCssComment(node.text, node.span, node.isTrailing);
+      ModifiableCssComment(node.text, node.span);
 
   ModifiableCssDeclaration visitCssDeclaration(CssDeclaration node) =>
       ModifiableCssDeclaration(node.name, node.value, node.span,
diff --git a/lib/src/visitor/evaluate.dart b/lib/src/visitor/evaluate.dart
index 3bd895346..38031840d 100644
--- a/lib/src/visitor/evaluate.dart
+++ b/lib/src/visitor/evaluate.dart
@@ -5,7 +5,7 @@
 // DO NOT EDIT. This file was generated from async_evaluate.dart.
 // See tool/grind/synchronize.dart for details.
 //
-// Checksum: 56067ad7a31ee7adf5bb4e9d484fe95f38d3762c
+// Checksum: f4f4c5d1cbc9894d14b6d8ce7c1a3c09146db9ba
 //
 // ignore_for_file: unused_import
 
@@ -1498,8 +1498,8 @@ class _EvaluateVisitor
       _endOfImports++;
     }
 
-    _parent.addChild(ModifiableCssComment(
-        _performInterpolation(node.text), node.span, node.isTrailing));
+    _parent.addChild(
+        ModifiableCssComment(_performInterpolation(node.text), node.span));
     return null;
   }
 
@@ -2409,8 +2409,7 @@ class _EvaluateVisitor
       _endOfImports++;
     }
 
-    _parent
-        .addChild(ModifiableCssComment(node.text, node.span, node.isTrailing));
+    _parent.addChild(ModifiableCssComment(node.text, node.span));
   }
 
   void visitCssDeclaration(CssDeclaration node) {
diff --git a/lib/src/visitor/serialize.dart b/lib/src/visitor/serialize.dart
index 2377d2568..f7c31d30d 100644
--- a/lib/src/visitor/serialize.dart
+++ b/lib/src/visitor/serialize.dart
@@ -156,19 +156,16 @@ class _SerializeVisitor
 
   void visitCssStylesheet(CssStylesheet node) {
     CssNode previous;
-    for (var i = 0; i < node.children.length; i++) {
-      var child = node.children[i];
+    for (CssNode child in node.children) {
       if (_isInvisible(child)) continue;
-
       if (previous != null) {
         if (_requiresSemicolon(previous)) _buffer.writeCharCode($semicolon);
-        if (_shouldWriteLineFeedBeforeChild(child)) {
-          _writeLineFeed();
-        } else {
+        if (_isTrailingComment(child, previous)) {
           _writeOptionalSpace();
+        } else {
+          _writeLineFeed();
+          if (previous.isGroupEnd) _writeLineFeed();
         }
-
-        if (previous.isGroupEnd) _writeLineFeed();
       }
       previous = child;
 
@@ -218,7 +215,7 @@ class _SerializeVisitor
 
     if (!node.isChildless) {
       _writeOptionalSpace();
-      _visitChildren(node.children);
+      _visitChildren(node.children, node);
     }
   }
 
@@ -236,7 +233,7 @@ class _SerializeVisitor
     });
 
     _writeOptionalSpace();
-    _visitChildren(node.children);
+    _visitChildren(node.children, node);
   }
 
   void visitCssImport(CssImport node) {
@@ -287,7 +284,7 @@ class _SerializeVisitor
         () =>
             _writeBetween(node.selector.value, _commaSeparator, _buffer.write));
     _writeOptionalSpace();
-    _visitChildren(node.children);
+    _visitChildren(node.children, node);
   }
 
   void _visitMediaQuery(CssMediaQuery query) {
@@ -312,7 +309,7 @@ class _SerializeVisitor
 
     _for(node.selector, () => node.selector.value.accept(this));
     _writeOptionalSpace();
-    _visitChildren(node.children);
+    _visitChildren(node.children, node);
   }
 
   void visitCssSupportsRule(CssSupportsRule node) {
@@ -329,7 +326,7 @@ class _SerializeVisitor
     });
 
     _writeOptionalSpace();
-    _visitChildren(node.children);
+    _visitChildren(node.children, node);
   }
 
   void visitCssDeclaration(CssDeclaration node) {
@@ -1083,7 +1080,7 @@ class _SerializeVisitor
       _for(value, () => _buffer.write(value.value));
 
   /// Emits [children] in a block.
-  void _visitChildren(List<CssNode> children) {
+  void _visitChildren(Iterable<CssNode> children, CssNode parent) {
     _buffer.writeCharCode($lbrace);
     if (children.every(_isInvisible)) {
       _buffer.writeCharCode($rbrace);
@@ -1091,38 +1088,37 @@ class _SerializeVisitor
     }
 
     bool indentNextChild;
-    if (_shouldWriteLineFeedBeforeChildren(children)) {
-      _writeLineFeed();
-      indentNextChild = true;
-    } else {
+    if (children.isNotEmpty && _isTrailingComment(children.first, parent)) {
       _writeOptionalSpace();
       indentNextChild = false;
+    } else {
+      _writeLineFeed();
+      indentNextChild = true;
     }
 
     CssNode previous;
     for (var child in children) {
-      var child = children[i];
       if (_isInvisible(child)) continue;
 
       if (previous != null) {
         if (_requiresSemicolon(previous)) _buffer.writeCharCode($semicolon);
-        if (_shouldWriteLineFeedBeforeChild(child)) {
-          _writeLineFeed();
-          indentNextChild = true;
-        } else {
+        if (_isTrailingComment(child, previous)) {
           _writeOptionalSpace();
           indentNextChild = false;
+        } else {
+          _writeLineFeed();
+          indentNextChild = true;
         }
         if (previous.isGroupEnd) _writeLineFeed();
       }
       previous = child;
 
       if (indentNextChild) {
-        _indentation++;
-      }
-      child.accept(this);
-      if (indentNextChild) {
-        _indentation--;
+        _indent(() {
+          child.accept(this);
+        });
+      } else {
+        child.accept(this);
       }
     }
 
@@ -1138,15 +1134,21 @@ class _SerializeVisitor
   bool _requiresSemicolon(CssNode node) =>
       node is CssParentNode ? node.isChildless : node is! CssComment;
 
-  /// Whether [child] should have a line feed written before the child is serialized.
-  bool _shouldWriteLineFeedBeforeChild(CssNode child) =>
-      child is! CssComment || !(child as CssComment).isTrailing;
+  /// Whether [node] represents a trailing comment when it appears after
+  /// [previous] in a sequence of nodes.  If there are no nodes before [node],
+  /// then [previous] should be the parent node.
+  bool _isTrailingComment(CssNode node, CssNode previous) {
+    if (node is CssComment) {
+      if (previous is CssParentNode) {
+        // TODO(nbehrens): Can we do better?
+        return node.span.start.line == previous.span.start.line ||
+            node.span.start.line == previous.span.end.line;
+      } else {
+        return node.span.start.line == previous.span.end.line;
+      }
+    }
 
-  /// Whether [children] should have a line feed written before the children are serialized.
-  bool _shouldWriteLineFeedBeforeChildren(List<CssNode> children) {
-    return children.isEmpty ||
-        !(children.first is CssComment) ||
-        !((children.first as CssComment).isTrailing);
+    return false;
   }
 
   /// Writes a line feed, unless this emitting compressed CSS.
@@ -1190,6 +1192,13 @@ class _SerializeVisitor
   /// Returns a comma used to separate values in lists.
   String get _commaSeparator => _isCompressed ? "," : ", ";
 
+  /// Runs [callback] with indentation increased one level.
+  void _indent(void callback()) {
+    _indentation++;
+    callback();
+    _indentation--;
+  }
+
   /// Returns whether [node] is considered invisible.
   bool _isInvisible(CssNode node) {
     if (_inspect) return false;
diff --git a/test/output_test.dart b/test/output_test.dart
index 484d5cb4c..f929011f9 100644
--- a/test/output_test.dart
+++ b/test/output_test.dart
@@ -60,33 +60,72 @@ void main() {
     });
   });
 
-  // Regression test for sass/dart-sass#417.
-  group("preserve trailing loud comments", () {
-    // No need for "in Sass" cases as it's not possible to have
-    // trailing loud comments in the Sass syntax.
-    group("in SCSS", () {
-      test("after open block", () {
-        expect(compileString("""
+  // Tests for sass/dart-sass#417.
+  //
+  // Note there's no need for "in Sass" cases as it's not possible to have
+  // trailing loud comments in the Sass syntax.
+  group("preserve trailing loud comments in SCSS", () {
+    test("after open block", () {
+      expect(compileString("""
 selector { /* please don't move me */
   name: value;
 }"""), equals("""
 selector { /* please don't move me */
   name: value;
 }"""));
-      });
-      test("after declaration", () {
-        expect(compileString("""
+    });
+
+    test("after close block", () {
+      expect(compileString("""
 selector {
-  name: value; /* please don't move me */
+  name: value;
+} /* please don't move me */"""), equals("""
+selector {
+  name: value;
+} /* please don't move me */"""));
+    });
+
+    test("only content in block", () {
+      expect(compileString("""
+selector {
+  /* please don't move me */
 }"""), equals("""
 selector {
-  name: value; /* please don't move me */
+  /* please don't move me */
 }"""));
-      });
-      test("after top-level statement", () {
-        expect(compileString("@rule; /* please don't move me */"),
-            equals("@rule; /* please don't move me */"));
-      });
+    });
+
+    test("after property in block", () {
+      expect(compileString("""
+selector {
+  name1: value1; /* please don't move me 1 */
+  name2: value2; /* please don't move me 2 */
+  name3: value3; /* please don't move me 3 */
+}"""), equals("""
+selector {
+  name1: value1; /* please don't move me 1 */
+  name2: value2; /* please don't move me 2 */
+  name3: value3; /* please don't move me 3 */
+}"""));
+    });
+
+    test("after rule in block", () {
+      expect(compileString("""
+selector {
+  @rule1; /* please don't move me 1 */
+  @rule2; /* please don't move me 2 */
+  @rule3; /* please don't move me 3 */
+}"""), equals("""
+selector {
+  @rule1; /* please don't move me 1 */
+  @rule2; /* please don't move me 2 */
+  @rule3; /* please don't move me 3 */
+}"""));
+    });
+
+    test("after top-level statement", () {
+      expect(compileString("@rule; /* please don't move me */"),
+          equals("@rule; /* please don't move me */"));
     });
   });
 }