diff --git a/src/Microsoft.AspNetCore.Razor.Language/DirectiveDescriptor.cs b/src/Microsoft.AspNetCore.Razor.Language/DirectiveDescriptor.cs
index afb315948f..f2591b9f68 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/DirectiveDescriptor.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/DirectiveDescriptor.cs
@@ -38,6 +38,11 @@ namespace Microsoft.AspNetCore.Razor.Language
         /// </summary>
         public abstract DirectiveKind Kind { get; }
 
+        /// <summary>
+        /// Gets the way a directive can be used. The usage determines how many, and where directives can exist per document.
+        /// </summary>
+        public abstract DirectiveUsage Usage { get; }
+
         /// <summary>
         /// Gets the list of directive tokens that can follow the directive keyword.
         /// </summary>
@@ -189,6 +194,8 @@ namespace Microsoft.AspNetCore.Razor.Language
 
             public DirectiveKind Kind { get; }
 
+            public DirectiveUsage Usage { get; set; }
+
             public IList<DirectiveTokenDescriptor> Tokens { get; }
 
             public DirectiveDescriptor Build()
@@ -218,7 +225,7 @@ namespace Microsoft.AspNetCore.Razor.Language
                     }
                 }
 
-                return new DefaultDirectiveDescriptor(Directive, Kind, Tokens.ToArray(), DisplayName, Description);
+                return new DefaultDirectiveDescriptor(Directive, Kind, Usage, Tokens.ToArray(), DisplayName, Description);
             }
         }
 
@@ -227,12 +234,14 @@ namespace Microsoft.AspNetCore.Razor.Language
             public DefaultDirectiveDescriptor(
                 string directive, 
                 DirectiveKind kind, 
+                DirectiveUsage usage,
                 DirectiveTokenDescriptor[] tokens,
                 string displayName,
                 string description)
             {
                 Directive = directive;
                 Kind = kind;
+                Usage = usage;
                 Tokens = tokens;
                 DisplayName = displayName;
                 Description = description;
@@ -246,6 +255,8 @@ namespace Microsoft.AspNetCore.Razor.Language
 
             public override DirectiveKind Kind { get; }
 
+            public override DirectiveUsage Usage { get; }
+
             public override IReadOnlyList<DirectiveTokenDescriptor> Tokens { get; }
         }
     }
diff --git a/src/Microsoft.AspNetCore.Razor.Language/DirectiveUsage.cs b/src/Microsoft.AspNetCore.Razor.Language/DirectiveUsage.cs
new file mode 100644
index 0000000000..5af9311748
--- /dev/null
+++ b/src/Microsoft.AspNetCore.Razor.Language/DirectiveUsage.cs
@@ -0,0 +1,11 @@
+// Copyright(c) .NET Foundation.All rights reserved.
+// Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
+
+namespace Microsoft.AspNetCore.Razor.Language
+{
+    public enum DirectiveUsage
+    {
+        Unrestricted,
+        FileScopedSinglyOccurring,
+    }
+}
diff --git a/src/Microsoft.AspNetCore.Razor.Language/IDirectiveDescriptorBuilder.cs b/src/Microsoft.AspNetCore.Razor.Language/IDirectiveDescriptorBuilder.cs
index c8e79d8d05..465069dbcf 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/IDirectiveDescriptorBuilder.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/IDirectiveDescriptorBuilder.cs
@@ -30,6 +30,11 @@ namespace Microsoft.AspNetCore.Razor.Language
         /// </summary>
         DirectiveKind Kind { get; }
 
+        /// <summary>
+        /// Gets or sets the directive usage. The usage determines how many, and where directives can exist per document.
+        /// </summary>
+        DirectiveUsage Usage { get; set; }
+
         /// <summary>
         /// Gets a list of the directive tokens.
         /// </summary>
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs b/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs
index 7533909396..8ad87468e0 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Legacy/BlockKindInternal.cs
@@ -8,13 +8,10 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
         // Code
         Statement,
         Directive,
-        Functions,
         Expression,
-        Helper,
 
         // Markup
         Markup,
-        Section,
         Template,
 
         // Special
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs b/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs
index f85d6b2d46..960cc7cf04 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs
@@ -54,6 +54,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
 
         private Dictionary<string, Action> _directiveParsers = new Dictionary<string, Action>(StringComparer.Ordinal);
         private Dictionary<CSharpKeyword, Action<bool>> _keywordParsers = new Dictionary<CSharpKeyword, Action<bool>>();
+        private HashSet<string> _seenDirectives = new HashSet<string>(StringComparer.Ordinal);
 
         public CSharpCodeParser(ParserContext context)
             : this(directives: Enumerable.Empty<DirectiveDescriptor>(), context: context)
@@ -91,7 +92,12 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
         {
             foreach (var directive in directives)
             {
-                _directiveParsers.Add(directive, handler);
+                _directiveParsers.Add(directive, () =>
+                {
+                    handler();
+                    _seenDirectives.Add(directive);
+                });
+
                 Keywords.Add(directive);
 
                 // These C# keywords are reserved for use in directives. It's an error to use them outside of
@@ -1589,10 +1595,13 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                 AcceptAndMoveNext();
                 Output(SpanKindInternal.MetaCode, AcceptedCharactersInternal.None);
 
+                // Even if an error was logged do not bail out early. If a directive was used incorrectly it doesn't mean it can't be parsed.
+                ValidateDirectiveUsage(descriptor);
+
                 for (var i = 0; i < descriptor.Tokens.Count; i++)
                 {
                     if (!At(CSharpSymbolType.WhiteSpace) &&
-                        !At(CSharpSymbolType.NewLine) && 
+                        !At(CSharpSymbolType.NewLine) &&
                         !EndOfFile)
                     {
                         Context.ErrorSink.OnError(
@@ -1767,6 +1776,56 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             }
         }
 
+
+        private void ValidateDirectiveUsage(DirectiveDescriptor descriptor)
+        {
+            if (descriptor.Usage == DirectiveUsage.FileScopedSinglyOccurring)
+            {
+                if (_seenDirectives.Contains(descriptor.Directive))
+                {
+                    UsageError(Resources.FormatDuplicateDirective(descriptor.Directive));
+                    return;
+                }
+
+                var root = Context.Builder.ActiveBlocks.Last();
+                for (var i = 0; i < root.Children.Count; i++)
+                {
+                    // Directives, comments and whitespace are valid prior to an unnested directive.
+
+                    var child = root.Children[i];
+                    if (child is Legacy.Block block)
+                    {
+                        if (block.Type == BlockKindInternal.Directive || block.Type == BlockKindInternal.Comment)
+                        {
+                            continue;
+                        }
+                    }
+                    else if (child is Span span)
+                    {
+                        if (span.Length == 0 ||
+                            span.Kind == SpanKindInternal.Comment ||
+                            span.Symbols.All(symbol => string.IsNullOrWhiteSpace(symbol.Content)))
+                        {
+                            continue;
+                        }
+                    }
+
+                    UsageError(Resources.FormatDirectiveMustExistBeforeMarkupOrCode(descriptor.Directive));
+                    return;
+                }
+            }
+
+            return;
+
+            void UsageError(string message)
+            {
+                // There wil always be at least 1 child because of the `@` transition.
+                var directiveStart = Context.Builder.CurrentBlock.Children.First().Start;
+                var errorLength = /* @ */ 1 + descriptor.Directive.Length;
+                Context.ErrorSink.OnError(directiveStart, message, errorLength);
+            }
+        }
+
         private void ParseDirectiveBlock(DirectiveDescriptor descriptor, Action<SourceLocation> parseChildren)
         {
             if (EndOfFile)
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Legacy/SyntaxTreeBuilder.cs b/src/Microsoft.AspNetCore.Razor.Language/Legacy/SyntaxTreeBuilder.cs
index 6dc4cac374..65db009fca 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Legacy/SyntaxTreeBuilder.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Legacy/SyntaxTreeBuilder.cs
@@ -17,7 +17,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             _endBlock = EndBlock;
         }
 
-        public IEnumerable<BlockBuilder> ActiveBlocks => _blockStack;
+        public IReadOnlyCollection<BlockBuilder> ActiveBlocks => _blockStack;
 
         public BlockBuilder CurrentBlock => _blockStack.Peek();
 
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs b/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs
index 602d0627af..f03e6bd554 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs
@@ -514,6 +514,34 @@ namespace Microsoft.AspNetCore.Razor.Language
         internal static string FormatIntermediateNodeReference_CollectionIsReadOnly(object p0)
             => string.Format(CultureInfo.CurrentCulture, GetString("IntermediateNodeReference_CollectionIsReadOnly"), p0);
 
+        /// <summary>
+        /// The '{0}' directive may only occur once per document.
+        /// </summary>
+        internal static string DuplicateDirective
+        {
+            get => GetString("DuplicateDirective");
+        }
+
+        /// <summary>
+        /// The '{0}' directive may only occur once per document.
+        /// </summary>
+        internal static string FormatDuplicateDirective(object p0)
+            => string.Format(CultureInfo.CurrentCulture, GetString("DuplicateDirective"), p0);
+
+        /// <summary>
+        /// The '{0}' directive must exist prior to markup or code.
+        /// </summary>
+        internal static string DirectiveMustExistBeforeMarkupOrCode
+        {
+            get => GetString("DirectiveMustExistBeforeMarkupOrCode");
+        }
+
+        /// <summary>
+        /// The '{0}' directive must exist prior to markup or code.
+        /// </summary>
+        internal static string FormatDirectiveMustExistBeforeMarkupOrCode(object p0)
+            => string.Format(CultureInfo.CurrentCulture, GetString("DirectiveMustExistBeforeMarkupOrCode"), p0);
+
         private static string GetString(string name, params string[] formatterNames)
         {
             var value = _resourceManager.GetString(name);
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Resources.resx b/src/Microsoft.AspNetCore.Razor.Language/Resources.resx
index f1ab0f0674..3298994894 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Resources.resx
+++ b/src/Microsoft.AspNetCore.Razor.Language/Resources.resx
@@ -225,4 +225,10 @@
   <data name="IntermediateNodeReference_CollectionIsReadOnly" xml:space="preserve">
     <value>The node '{0}' has a read-only child collection and cannot be modified.</value>
   </data>
+  <data name="DuplicateDirective" xml:space="preserve">
+    <value>The '{0}' directive may only occur once per document.</value>
+  </data>
+  <data name="DirectiveMustExistBeforeMarkupOrCode" xml:space="preserve">
+    <value>The '{0}' directive must exist prior to markup or code.</value>
+  </data>
 </root>
\ No newline at end of file
diff --git a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/BlockTest.cs b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/BlockTest.cs
index f182c224a9..aa826bb323 100644
--- a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/BlockTest.cs
+++ b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/BlockTest.cs
@@ -30,7 +30,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             var expected = new ExpressionChunkGenerator();
             var builder = new BlockBuilder()
             {
-                Type = BlockKindInternal.Helper,
+                Type = BlockKindInternal.Statement,
                 ChunkGenerator = expected
             };
 
@@ -48,7 +48,7 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             var expected = new SpanBuilder(SourceLocation.Undefined) { Kind = SpanKindInternal.Code }.Build();
             var builder = new BlockBuilder()
             {
-                Type = BlockKindInternal.Functions
+                Type = BlockKindInternal.Statement
             };
             builder.Children.Add(expected);
 
diff --git a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs
index 4c48b7a8de..19e0b6aa5c 100644
--- a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs
+++ b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs
@@ -11,6 +11,295 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
 {
     public class CSharpDirectivesTest : CsHtmlCodeParserTestBase
     {
+        [Fact]
+        public void DirectiveDescriptor_SinglePreContent_ErrorsIfNestedInCode()
+        {
+            // Arrange
+            var descriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddTypeToken();
+                });
+            var chunkGenerator = new DirectiveChunkGenerator(descriptor);
+            chunkGenerator.Diagnostics.Add(
+                RazorDiagnostic.Create(
+                    new RazorError(
+                        Resources.FormatDirectiveMustExistBeforeMarkupOrCode("custom"),
+                        1 + Environment.NewLine.Length, 1, 0, 7)));
+
+            // Act & Assert
+            ParseCodeBlockTest(
+@"{
+@custom System.Text.Encoding.ASCIIEncoding
+}",
+                new[] { descriptor },
+                new StatementBlock(
+                    Factory.MetaCode("{").Accepts(AcceptedCharactersInternal.None),
+                    Factory.Code(Environment.NewLine)
+                        .AsStatement()
+                        .AutoCompleteWith(autoCompleteString: null, atEndOfSpan: false),
+                    new DirectiveBlock(chunkGenerator,
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("custom").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "System.Text.Encoding.ASCIIEncoding", markup: false).AsDirectiveToken(descriptor.Tokens[0]),
+                        Factory.MetaCode(Environment.NewLine).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    Factory.EmptyCSharp().AsStatement(),
+                    Factory.MetaCode("}").Accepts(AcceptedCharactersInternal.None)));
+        }
+
+        [Fact]
+        public void DirectiveDescriptor_SinglePreContent_ErrorsIfNestedInHtml()
+        {
+            // Arrange
+            var descriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddTypeToken();
+                });
+            var chunkGenerator = new DirectiveChunkGenerator(descriptor);
+            chunkGenerator.Diagnostics.Add(
+                RazorDiagnostic.Create(
+                    new RazorError(
+                        Resources.FormatDirectiveMustExistBeforeMarkupOrCode("custom"),
+                        3 + Environment.NewLine.Length, 1, 0, 7)));
+
+            // Act & Assert
+            ParseDocumentTest(
+@"<p>
+@custom System.Text.Encoding.ASCIIEncoding
+</p>",
+                new[] { descriptor },
+                new MarkupBlock(
+                    BlockFactory.MarkupTagBlock("<p>"),
+                    Factory.Markup(Environment.NewLine),
+                    new DirectiveBlock(chunkGenerator,
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("custom").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "System.Text.Encoding.ASCIIEncoding", markup: false).AsDirectiveToken(descriptor.Tokens[0]),
+                        Factory.MetaCode(Environment.NewLine).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    BlockFactory.MarkupTagBlock("</p>")));
+        }
+
+        [Fact]
+        public void DirectiveDescriptor_SinglePreContent_ErrorsIfDuplicate()
+        {
+            // Arrange
+            var descriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddTypeToken();
+                });
+            var chunkGenerator = new DirectiveChunkGenerator(descriptor);
+            chunkGenerator.Diagnostics.Add(
+                RazorDiagnostic.Create(
+                    new RazorError(
+                        Resources.FormatDuplicateDirective("custom"),
+                        42 + Environment.NewLine.Length, 1, 0, 7)));
+
+            // Act & Assert
+            ParseDocumentTest(
+@"@custom System.Text.Encoding.ASCIIEncoding
+@custom System.Text.Encoding.UTF8Encoding",
+                new[] { descriptor },
+                new MarkupBlock(
+                    Factory.EmptyHtml(),
+                    new DirectiveBlock(new DirectiveChunkGenerator(descriptor),
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("custom").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "System.Text.Encoding.ASCIIEncoding", markup: false).AsDirectiveToken(descriptor.Tokens[0]),
+                        Factory.MetaCode(Environment.NewLine).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    Factory.EmptyHtml(),
+                    new DirectiveBlock(chunkGenerator,
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("custom").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "System.Text.Encoding.UTF8Encoding", markup: false).AsDirectiveToken(descriptor.Tokens[0])),
+                    Factory.EmptyHtml()));
+        }
+
+        [Fact]
+        public void DirectiveDescriptor_SinglePreContent_CanBeBeneathOtherDirectives()
+        {
+            // Arrange
+            var customDescriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddTypeToken();
+                });
+            var somethingDescriptor = DirectiveDescriptor.CreateDirective(
+                "something",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddMemberToken();
+                });
+
+            // Act & Assert
+            ParseDocumentTest(
+@"@custom System.Text.Encoding.ASCIIEncoding
+@something Else",
+                new[] { customDescriptor, somethingDescriptor },
+                new MarkupBlock(
+                    Factory.EmptyHtml(),
+                    new DirectiveBlock(new DirectiveChunkGenerator(customDescriptor),
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("custom").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "System.Text.Encoding.ASCIIEncoding", markup: false).AsDirectiveToken(customDescriptor.Tokens[0]),
+                        Factory.MetaCode(Environment.NewLine).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    Factory.EmptyHtml(),
+                    new DirectiveBlock(new DirectiveChunkGenerator(somethingDescriptor),
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("something").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "Else", markup: false).AsDirectiveToken(somethingDescriptor.Tokens[0])),
+                    Factory.EmptyHtml()));
+        }
+
+        [Fact]
+        public void DirectiveDescriptor_SinglePreContent_CanBeBeneathOtherWhiteSpaceCommentsAndDirectives()
+        {
+            // Arrange
+            var customDescriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddTypeToken();
+                });
+            var somethingDescriptor = DirectiveDescriptor.CreateDirective(
+                "something",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddMemberToken();
+                });
+
+            // Act & Assert
+            ParseDocumentTest(
+@"@* There are two directives beneath this *@
+@custom System.Text.Encoding.ASCIIEncoding
+
+@something Else
+
+<p>This is extra</p>",
+                new[] { customDescriptor, somethingDescriptor },
+                new MarkupBlock(
+                    Factory.EmptyHtml(),
+                    new CommentBlock(
+                        Factory.MarkupTransition(HtmlSymbolType.RazorCommentTransition).Accepts(AcceptedCharactersInternal.None),
+                        Factory.MetaMarkup("*", HtmlSymbolType.RazorCommentStar).Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Comment, new HtmlSymbol(" There are two directives beneath this ", HtmlSymbolType.RazorComment)).Accepts(AcceptedCharactersInternal.Any),
+                        Factory.MetaMarkup("*", HtmlSymbolType.RazorCommentStar).Accepts(AcceptedCharactersInternal.None),
+                        Factory.MarkupTransition(HtmlSymbolType.RazorCommentTransition).Accepts(AcceptedCharactersInternal.None)),
+                    Factory.Markup(Environment.NewLine),
+                    new DirectiveBlock(new DirectiveChunkGenerator(customDescriptor),
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("custom").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "System.Text.Encoding.ASCIIEncoding", markup: false).AsDirectiveToken(customDescriptor.Tokens[0]),
+                        Factory.MetaCode(Environment.NewLine).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    Factory.Markup(Environment.NewLine),
+                    new DirectiveBlock(new DirectiveChunkGenerator(somethingDescriptor),
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("something").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "Else", markup: false).AsDirectiveToken(somethingDescriptor.Tokens[0]),
+                        Factory.MetaCode(Environment.NewLine).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    Factory.Markup(Environment.NewLine),
+                    BlockFactory.MarkupTagBlock("<p>"),
+                    Factory.Markup("This is extra"),
+                    BlockFactory.MarkupTagBlock("</p>")));
+        }
+
+        [Fact]
+        public void DirectiveDescriptor_SinglePreContent_MixedContentErrors()
+        {
+            // Arrange
+            var customDescriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddTypeToken();
+                });
+            var somethingDescriptor = DirectiveDescriptor.CreateDirective(
+                "something",
+                DirectiveKind.SingleLine,
+                builder =>
+                {
+                    builder.Usage = DirectiveUsage.SinglePreContent;
+                    builder.AddMemberToken();
+                });
+            var chunkGenerator = new DirectiveChunkGenerator(somethingDescriptor);
+            chunkGenerator.Diagnostics.Add(
+                RazorDiagnostic.Create(
+                    new RazorError(
+                        Resources.FormatDirectiveMustExistBeforeMarkupOrCode("something"),
+                        151 + Environment.NewLine.Length * 4, 4, 0, 10)));
+
+            // Act & Assert
+            ParseDocumentTest(
+@"@custom System.Text.Encoding.ASCIIEncoding
+@* There is invalid content beneath this *@
+<p>Should cause error</p>
+@* There is invalid content above this *@
+@something Else",
+                new[] { customDescriptor, somethingDescriptor },
+                new MarkupBlock(
+                    Factory.EmptyHtml(),
+                    new DirectiveBlock(new DirectiveChunkGenerator(customDescriptor),
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("custom").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "System.Text.Encoding.ASCIIEncoding", markup: false).AsDirectiveToken(customDescriptor.Tokens[0]),
+                        Factory.MetaCode(Environment.NewLine).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    Factory.EmptyHtml(),
+                    new CommentBlock(
+                        Factory.MarkupTransition(HtmlSymbolType.RazorCommentTransition).Accepts(AcceptedCharactersInternal.None),
+                        Factory.MetaMarkup("*", HtmlSymbolType.RazorCommentStar).Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Comment, new HtmlSymbol(" There is invalid content beneath this ", HtmlSymbolType.RazorComment)).Accepts(AcceptedCharactersInternal.Any),
+                        Factory.MetaMarkup("*", HtmlSymbolType.RazorCommentStar).Accepts(AcceptedCharactersInternal.None),
+                        Factory.MarkupTransition(HtmlSymbolType.RazorCommentTransition).Accepts(AcceptedCharactersInternal.None)),
+                    Factory.Markup(Environment.NewLine),
+                    BlockFactory.MarkupTagBlock("<p>"),
+                    Factory.Markup("Should cause error"),
+                    BlockFactory.MarkupTagBlock("</p>"),
+                    Factory.Markup(Environment.NewLine),
+                    new CommentBlock(
+                        Factory.MarkupTransition(HtmlSymbolType.RazorCommentTransition).Accepts(AcceptedCharactersInternal.None),
+                        Factory.MetaMarkup("*", HtmlSymbolType.RazorCommentStar).Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Comment, new HtmlSymbol(" There is invalid content above this ", HtmlSymbolType.RazorComment)).Accepts(AcceptedCharactersInternal.Any),
+                        Factory.MetaMarkup("*", HtmlSymbolType.RazorCommentStar).Accepts(AcceptedCharactersInternal.None),
+                        Factory.MarkupTransition(HtmlSymbolType.RazorCommentTransition).Accepts(AcceptedCharactersInternal.None)),
+                    Factory.Markup(Environment.NewLine).With(SpanChunkGenerator.Null),
+                    new DirectiveBlock(chunkGenerator,
+                        Factory.CodeTransition(),
+                        Factory.MetaCode("something").Accepts(AcceptedCharactersInternal.None),
+                        Factory.Span(SpanKindInternal.Code, " ", markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace),
+                        Factory.Span(SpanKindInternal.Code, "Else", markup: false).AsDirectiveToken(somethingDescriptor.Tokens[0])),
+                    Factory.EmptyHtml()));
+        }
+
         [Fact]
         public void DirectiveDescriptor_TokensMustBeSeparatedBySpace()
         {