diff --git a/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs b/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs
index 621d7f666e..6d45b45404 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Legacy/CSharpCodeParser.cs
@@ -101,7 +101,11 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
         {
             foreach (var directive in directives)
             {
-                _directiveParsers.Add(directive, handler);
+                _directiveParsers.Add(directive, () =>
+                {
+                    EnsureDirectiveIsAtStartOfLine();
+                    handler();
+                });
                 Keywords.Add(directive);
 
                 // These C# keywords are reserved for use in directives. It's an error to use them outside of
@@ -1519,6 +1523,30 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
             MapDirectives(RemoveTagHelperDirective, SyntaxConstants.CSharp.RemoveTagHelperKeyword);
         }
 
+        private void EnsureDirectiveIsAtStartOfLine()
+        {
+            // 1 is the offset of the @ transition for the directive.
+            if (CurrentStart.CharacterIndex > 1)
+            {
+                var index = CurrentStart.AbsoluteIndex - 1;
+                var lineStart = CurrentStart.AbsoluteIndex - CurrentStart.CharacterIndex;
+                while (--index >= lineStart)
+                {
+                    var @char = Context.SourceDocument[index];
+
+                    if (!char.IsWhiteSpace(@char))
+                    {
+                        var currentDirective = CurrentSymbol.Content;
+                        Context.ErrorSink.OnError(
+                            CurrentStart,
+                            Resources.FormatDirectiveMustAppearAtStartOfLine(currentDirective),
+                            length: currentDirective.Length);
+                        break;
+                    }
+                }
+            }
+        }
+
         private void HandleDirective(DirectiveDescriptor descriptor)
         {
             Context.Builder.CurrentBlock.Type = BlockKindInternal.Directive;
diff --git a/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs b/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs
index 1f41dd4ab7..89459d415c 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs
+++ b/src/Microsoft.AspNetCore.Razor.Language/Properties/Resources.Designer.cs
@@ -430,6 +430,20 @@ namespace Microsoft.AspNetCore.Razor.Language
         internal static string FormatDiagnostic_CodeTarget_UnsupportedExtension(object p0, object p1)
             => string.Format(CultureInfo.CurrentCulture, GetString("Diagnostic_CodeTarget_UnsupportedExtension"), p0, p1);
 
+        /// <summary>
+        /// The '{0}` directive must appear at the start of the line.
+        /// </summary>
+        internal static string DirectiveMustAppearAtStartOfLine
+        {
+            get => GetString("DirectiveMustAppearAtStartOfLine");
+        }
+
+        /// <summary>
+        /// The '{0}` directive must appear at the start of the line.
+        /// </summary>
+        internal static string FormatDirectiveMustAppearAtStartOfLine(object p0)
+            => string.Format(CultureInfo.CurrentCulture, GetString("DirectiveMustAppearAtStartOfLine"), 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 85d8d679b3..b05f1016c4 100644
--- a/src/Microsoft.AspNetCore.Razor.Language/Resources.resx
+++ b/src/Microsoft.AspNetCore.Razor.Language/Resources.resx
@@ -207,4 +207,7 @@
   <data name="Diagnostic_CodeTarget_UnsupportedExtension" xml:space="preserve">
     <value>The document type '{0}' does not support the extension '{1}'.</value>
   </data>
+  <data name="DirectiveMustAppearAtStartOfLine" xml:space="preserve">
+    <value>The '{0}` directive must appear at the start of the line.</value>
+  </data>
 </root>
\ No newline at end of file
diff --git a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs
index d9897cfba5..f51d8e33b1 100644
--- a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs
+++ b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpDirectivesTest.cs
@@ -10,6 +10,104 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
 {
     public class CSharpDirectivesTest : CsHtmlCodeParserTestBase
     {
+        [Fact]
+        public void ExtensibleDirectiveDoesNotErorrIfNotAtStartOfLineBecauseOfWhitespace()
+        {
+            // Arrange
+            var descriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                b => b.AddTypeToken());
+
+            // Act & Assert
+            ParseCodeBlockTest(Environment.NewLine + "  @custom System.Text.Encoding.ASCIIEncoding",
+                new[] { descriptor },
+                new DirectiveBlock(
+                    new DirectiveChunkGenerator(descriptor),
+                    Factory.Code(Environment.NewLine + "  ").AsStatement(),
+                    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)
+                        .With(new DirectiveTokenChunkGenerator(descriptor.Tokens[0]))
+                        .Accepts(AcceptedCharactersInternal.NonWhiteSpace)));
+        }
+
+        [Fact]
+        public void BuiltInDirectiveDoesNotErorrIfNotAtStartOfLineBecauseOfWhitespace()
+        {
+            // Act & Assert
+            ParseCodeBlockTest(Environment.NewLine + "  @addTagHelper \"*, Foo\"",
+                Enumerable.Empty<DirectiveDescriptor>(),
+                new DirectiveBlock(
+                    Factory.Code(Environment.NewLine + "  ").AsStatement(),
+                    Factory.CodeTransition(),
+                    Factory.MetaCode(SyntaxConstants.CSharp.AddTagHelperKeyword + " ")
+                            .Accepts(AcceptedCharactersInternal.None),
+                    Factory.Code("\"*, Foo\"")
+                        .AsAddTagHelper("\"*, Foo\"")));
+        }
+
+        [Fact]
+        public void BuiltInDirectiveErorrsIfNotAtStartOfLine()
+        {
+            // Act & Assert
+            ParseCodeBlockTest("{  @addTagHelper \"*, Foo\"" + Environment.NewLine + "}",
+                Enumerable.Empty<DirectiveDescriptor>(),
+                new StatementBlock(
+                    Factory.MetaCode("{").Accepts(AcceptedCharactersInternal.None),
+                    Factory.Code("  ")
+                        .AsStatement()
+                        .AutoCompleteWith(autoCompleteString: null, atEndOfSpan: false),
+                    new DirectiveBlock(
+                        Factory.CodeTransition(),
+                        Factory.MetaCode(SyntaxConstants.CSharp.AddTagHelperKeyword + " ")
+                               .Accepts(AcceptedCharactersInternal.None),
+                        Factory.Code("\"*, Foo\"")
+                            .AsAddTagHelper("\"*, Foo\"")),
+                    Factory.Code(Environment.NewLine).AsStatement(),
+                    Factory.MetaCode("}").Accepts(AcceptedCharactersInternal.None)),
+                new RazorError(
+                        Resources.FormatDirectiveMustAppearAtStartOfLine("addTagHelper"),
+                        new SourceLocation(4, 0, 4),
+                        12));
+        }
+
+        [Fact]
+        public void ExtensibleDirectiveErorrsIfNotAtStartOfLine()
+        {
+            // Arrange
+            var descriptor = DirectiveDescriptor.CreateDirective(
+                "custom",
+                DirectiveKind.SingleLine,
+                b => b.AddTypeToken());
+
+            // Act & Assert
+            ParseCodeBlockTest(
+                "{  @custom System.Text.Encoding.ASCIIEncoding" + Environment.NewLine + "}",
+                new[] { descriptor },
+                new StatementBlock(
+                    Factory.MetaCode("{").Accepts(AcceptedCharactersInternal.None),
+                    Factory.Code("  ")
+                        .AsStatement()
+                        .AutoCompleteWith(autoCompleteString: null, atEndOfSpan: false),
+                    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)
+                            .With(new DirectiveTokenChunkGenerator(descriptor.Tokens[0]))
+                            .Accepts(AcceptedCharactersInternal.NonWhiteSpace),
+                        Factory.Span(SpanKindInternal.Markup, Environment.NewLine, markup: false).Accepts(AcceptedCharactersInternal.WhiteSpace)),
+                    Factory.EmptyCSharp().AsStatement(),
+                    Factory.MetaCode("}").Accepts(AcceptedCharactersInternal.None)),
+                new RazorError(
+                    Resources.FormatDirectiveMustAppearAtStartOfLine("custom"),
+                    new SourceLocation(4, 0, 4),
+                    6));
+        }
+
         [Fact]
         public void DirectiveDescriptor_UnderstandsTypeTokens()
         {
diff --git a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpSectionTest.cs b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpSectionTest.cs
index a05f37dd26..3f4511525a 100644
--- a/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpSectionTest.cs
+++ b/test/Microsoft.AspNetCore.Razor.Language.Test/Legacy/CSharpSectionTest.cs
@@ -164,6 +164,10 @@ namespace Microsoft.AspNetCore.Razor.Language.Legacy
                             Factory.Markup(" ")),
                         Factory.MetaCode("}").Accepts(AcceptedCharactersInternal.None)),
                     Factory.EmptyHtml()),
+                new RazorError(
+                    Resources.FormatDirectiveMustAppearAtStartOfLine("section"),
+                    new SourceLocation(16, 0, 16),
+                    7),
                 new RazorError(
                     LegacyResources.FormatParseError_Sections_Cannot_Be_Nested(LegacyResources.SectionExample_CS),
                     new SourceLocation(15, 0, 15),