diff --git a/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs b/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs
index c515770ca7..9f9886164c 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs
@@ -18,6 +18,8 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
 
         // Special
         Comment = 8,
-        Tag = 9
+        Tag = 9,
+
+        HtmlComment = 10
     }
 }
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Legacy/HtmlMarkupParser.cs b/src/Microsoft.AspNetCore.Razor.Language/Legacy/HtmlMarkupParser.cs
index 4fdee1322f..332023b775 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Legacy/HtmlMarkupParser.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Legacy/HtmlMarkupParser.cs
@@ -207,6 +207,10 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             if (last != null)
             {
                 Accept(last);
+                if (At(HtmlSymbolType.OpenAngle) && last.Type == HtmlSymbolType.Text)
+                {
+                    Output(SpanKindInternal.Markup);
+                }
             }
         }
 
@@ -494,26 +498,34 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             {
                 if (CurrentSymbol.Type == HtmlSymbolType.DoubleHyphen)
                 {
-                    AcceptAndMoveNext();
-
-                    Span.EditHandler.AcceptedCharacters = AcceptedCharactersInternal.Any;
-                    while (!EndOfFile)
+                    using (Context.Builder.StartBlock(BlockKindInternal.HtmlComment))
                     {
-                        SkipToAndParseCode(HtmlSymbolType.DoubleHyphen);
-                        if (At(HtmlSymbolType.DoubleHyphen))
+                        AcceptAndMoveNext();
+
+                        Span.EditHandler.AcceptedCharacters = AcceptedCharactersInternal.Any;
+                        while (!EndOfFile)
                         {
-                            AcceptWhile(HtmlSymbolType.DoubleHyphen);
-
-                            if (At(HtmlSymbolType.Text) &&
-                                string.Equals(CurrentSymbol.Content, "-", StringComparison.Ordinal))
+                            SkipToAndParseCode(HtmlSymbolType.DoubleHyphen);
+                            if (At(HtmlSymbolType.DoubleHyphen))
                             {
-                                AcceptAndMoveNext();
-                            }
+                                AcceptWhile(HtmlSymbolType.DoubleHyphen);
 
-                            if (At(HtmlSymbolType.CloseAngle))
-                            {
-                                AcceptAndMoveNext();
-                                return true;
+                                if (At(HtmlSymbolType.Text) &&
+                                    string.Equals(CurrentSymbol.Content, "-", StringComparison.Ordinal))
+                                {
+                                    AcceptAndMoveNext();
+                                }
+
+                                if (At(HtmlSymbolType.CloseAngle))
+                                {
+                                    // This is the end of a comment block
+                                    Accept(this.CurrentSymbol);
+                                    Output(SpanKindInternal.Markup);
+
+                                    NextToken();
+                                    //AcceptAndMoveNext();
+                                    return true;
+                                }
                             }
                         }
                     }
@@ -1476,6 +1488,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                     {
                         AcceptAndMoveNext(); // Accept '<'
                         BangTag();
+
                         return;
                     }
 
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Legacy/TagHelperParseTreeRewriter.cs b/src/Microsoft.AspNetCore.Razor.Language/Legacy/TagHelperParseTreeRewriter.cs
index 930b928949..6cac8b46ea 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Legacy/TagHelperParseTreeRewriter.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Legacy/TagHelperParseTreeRewriter.cs
@@ -488,7 +488,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
 
         private void ValidateParentAllowsContent(Span child, ErrorSink errorSink)
         {
-            if (HasAllowedChildren() && !IsComment(child))
+            if (HasAllowedChildren() && !IsComment(child) && child.Kind != SpanKindInternal.Transition && child.Kind != SpanKindInternal.Code)
             {
                 var content = child.Content;
                 if (!string.IsNullOrWhiteSpace(content))
@@ -817,14 +817,18 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             return relevantSymbol.Type == HtmlSymbolType.ForwardSlash;
         }
 
-        private static bool IsComment(Span span)
+        internal static bool IsComment(Span span)
         {
-            bool isHtmlComment = span.Content?.StartsWith("<!--") == true;
-            bool isRazorComment = span.Parent?.Type == BlockKindInternal.Comment;
+            Block currentBlock = span.Parent;
+            while (currentBlock != null && currentBlock.Type != BlockKindInternal.Comment && currentBlock.Type != BlockKindInternal.HtmlComment)
+            {
+                currentBlock = currentBlock.Parent;
+            }
 
-            return isHtmlComment || isRazorComment;
+            return currentBlock != null;
         }
 
+
         private static void EnsureTagBlock(Block tagBlock)
         {
             Debug.Assert(tagBlock.Type == BlockKindInternal.Tag);
diff --git a/src/Microsoft.VisualStudio.Editor.Razor/BlockKind.cs b/src/Microsoft.VisualStudio.Editor.Razor/BlockKind.cs
index 48ad2e4fb4..2559231329 100644
--- a/src/Microsoft.VisualStudio.Editor.Razor/BlockKind.cs
+++ b/src/Microsoft.VisualStudio.Editor.Razor/BlockKind.cs
@@ -19,6 +19,8 @@ namespace Microsoft.VisualStudio.Editor.Razor
 
         // Special
         Comment,
-        Tag
+        Tag,
+
+        HtmlComment
     }
 }
diff --git a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/TagHelperParseTreeRewriterTest.cs b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/TagHelperParseTreeRewriterTest.cs
index 4a640b1990..45a1ffa907 100644
--- a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/TagHelperParseTreeRewriterTest.cs
+++ b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/TagHelperParseTreeRewriterTest.cs
@@ -1109,12 +1109,12 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
         }
 
         [Fact]
-        public void Rewrite_AllowsHtmlCommentsAsChildren()
+        public void Rewrite_AllowsSimpleHtmlCommentsAsChildren()
         {
             // Arrangestring documentContent,
             IEnumerable<string> allowedChildren = new List<string> { "b" };
             string literal = "asdf";
-            string commentOutput = $"<!--Hello World-->";
+            string commentOutput = "<!--Hello World-->";
             string expectedOutput = $"<p><b>{literal}</b>{commentOutput}</p>";
 
             var pTagHelperBuilder = TagHelperDescriptorBuilder
@@ -1138,7 +1138,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                     blockFactory.MarkupTagBlock("<b>"),
                     factory.Markup(literal),
                     blockFactory.MarkupTagBlock("</b>"),
-                    factory.Markup(commentOutput)));
+                    new HtmlCommentBlock(factory.Markup(commentOutput))));
 
             // Act & Assert
             EvaluateData(
@@ -1148,6 +1148,58 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                 Array.Empty<RazorDiagnostic>());
         }
 
+        [Fact]
+        public void Rewrite_FailsForContentWithCommentsAsChildren()
+        {
+            // Arrangestring documentContent,
+            Func<string, string, string, int, int, RazorDiagnostic> nestedTagError =
+                    (childName, parentName, allowed, location, length) =>
+                    RazorDiagnosticFactory.CreateTagHelper_InvalidNestedTag(
+                        new SourceSpan(absoluteIndex: location, lineIndex: 0, characterIndex: location, length: length), childName, parentName, allowed);
+            Func<string, string, int, int, RazorDiagnostic> nestedContentError =
+                (parentName, allowed, location, length) =>
+                RazorDiagnosticFactory.CreateTagHelper_CannotHaveNonTagContent(
+                    new SourceSpan(absoluteIndex: location, lineIndex: 0, characterIndex: location, length: length), parentName, allowed);
+
+            IEnumerable<string> allowedChildren = new List<string> { "b" };
+            string comment1 = "Hello";
+            string literal = "asdf";
+            string comment2 = "World";
+            string expectedOutput = $"<p><!--{comment1}-->{literal}<!--{comment2}--></p>";
+
+            var pTagHelperBuilder = TagHelperDescriptorBuilder
+                .Create("PTagHelper", "SomeAssembly")
+                .TagMatchingRuleDescriptor(rule => rule.RequireTagName("p"));
+            foreach (var childTag in allowedChildren)
+            {
+                pTagHelperBuilder.AllowChildTag(childTag);
+            }
+
+            var descriptors = new TagHelperDescriptor[]
+            {
+                pTagHelperBuilder.Build()
+            };
+
+            var factory = new SpanFactory();
+            var blockFactory = new BlockFactory(factory);
+
+            var expectedMarkup = new MarkupBlock(
+                new MarkupTagHelperBlock("p",
+                    new HtmlCommentBlock(factory.Markup($"<!--{comment1}-->")),
+                    factory.Markup(literal),
+                    new HtmlCommentBlock(factory.Markup($"<!--{comment2}-->"))));
+
+            // Act & Assert
+            EvaluateData(
+                descriptors,
+                expectedOutput,
+                expectedMarkup,
+                new[]
+                {
+                    nestedContentError("p", "b", 15, 4),
+                });
+        }
+
         [Fact]
         public void Rewrite_AllowsRazorCommentsAsChildren()
         {
@@ -1193,6 +1245,54 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                 Array.Empty<RazorDiagnostic>());
         }
 
+        [Fact]
+        public void Rewrite_AllowsRazorMarkupInHtmlComment()
+        {
+            // Arrangestring documentContent,
+            IEnumerable<string> allowedChildren = new List<string> { "b" };
+            string literal = "asdf";
+            string part1 = "<!--Hello ";
+            string part2 = "World";
+            string part3 = "-->";
+            string expectedOutput = $"<p><b>{literal}</b>{part1}@{part2}{part3}</p>";
+
+            var pTagHelperBuilder = TagHelperDescriptorBuilder
+                .Create("PTagHelper", "SomeAssembly")
+                .TagMatchingRuleDescriptor(rule => rule.RequireTagName("p"));
+            foreach (var childTag in allowedChildren)
+            {
+                pTagHelperBuilder.AllowChildTag(childTag);
+            }
+
+            var descriptors = new TagHelperDescriptor[]
+            {
+                pTagHelperBuilder.Build()
+            };
+
+            var factory = new SpanFactory();
+            var blockFactory = new BlockFactory(factory);
+
+            var expectedMarkup = new MarkupBlock(
+                new MarkupTagHelperBlock("p",
+                    blockFactory.MarkupTagBlock("<b>"),
+                    factory.Markup(literal),
+                    blockFactory.MarkupTagBlock("</b>"),
+                    new HtmlCommentBlock(factory.Markup(part1),
+                     new ExpressionBlock(
+                        factory.CodeTransition(),
+                        factory.Code(part2)
+                            .AsImplicitExpression(CSharpCodeParser.DefaultKeywords)
+                            .Accepts(AcceptedCharactersInternal.NonWhiteSpace)),
+                    factory.Markup(part3))));
+
+            // Act & Assert
+            EvaluateData(
+                descriptors,
+                expectedOutput,
+                expectedMarkup,
+                Array.Empty<RazorDiagnostic>());
+        }
+
         [Fact]
         public void Rewrite_UnderstandsNullTagNameWithAllowedChildrenForCatchAll()
         {
@@ -3993,7 +4093,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                     new MarkupBlock(
                         new MarkupTagBlock(
                             factory.Markup("<foo>")),
-                        factory.Markup("<!-- Hello World -->"),
+                        new HtmlCommentBlock( factory.Markup("<!-- Hello World -->")),
                         new MarkupTagBlock(
                             factory.Markup("</foo>")))
                 };
@@ -4003,13 +4103,13 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                     new MarkupBlock(
                         new MarkupTagBlock(
                             factory.Markup("<foo>")),
-                        factory.Markup("<!-- "),
-                        new ExpressionBlock(
-                            factory.CodeTransition(),
-                            factory.Code("foo")
-                                   .AsImplicitExpression(CSharpCodeParser.DefaultKeywords)
-                                   .Accepts(AcceptedCharactersInternal.NonWhiteSpace)),
-                        factory.Markup(" -->"),
+                        new HtmlCommentBlock(factory.Markup("<!-- "),
+                            new ExpressionBlock(
+                                factory.CodeTransition(),
+                                factory.Code("foo")
+                                       .AsImplicitExpression(CSharpCodeParser.DefaultKeywords)
+                                       .Accepts(AcceptedCharactersInternal.NonWhiteSpace)),
+                            factory.Markup(" -->")),
                         new MarkupTagBlock(
                             factory.Markup("</foo>")))
                 };
diff --git a/test/Microsoft.AspNetCore.Razor.Test.Common/Language/Legacy/BlockTypes.cs b/test/Microsoft.AspNetCore.Razor.Test.Common/Language/Legacy/BlockTypes.cs
index c08e88d56f..56deb6b460 100644
--- a/test/Microsoft.AspNetCore.Razor.Test.Common/Language/Legacy/BlockTypes.cs
+++ b/test/Microsoft.AspNetCore.Razor.Test.Common/Language/Legacy/BlockTypes.cs
@@ -217,4 +217,14 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
         {
         }
     }
+
+    internal class HtmlCommentBlock : Block
+    {
+        private const BlockKindInternal ThisBlockKind = BlockKindInternal.HtmlComment;
+
+        public HtmlCommentBlock(params SyntaxTreeNode[] children)
+            : base(ThisBlockKind, children, ParentChunkGenerator.Null)
+        {
+        }
+    }
 }