diff --git a/src/EditorFeatures/CSharpTest2/Recommendations/ThisKeywordRecommenderTests.cs b/src/EditorFeatures/CSharpTest2/Recommendations/ThisKeywordRecommenderTests.cs
index 3a6418d0c8f73b9daeba722ce94e36e0e3661900..8f2a26a7b2a4695b253bebe5b0153a4bb1a3dfea 100644
--- a/src/EditorFeatures/CSharpTest2/Recommendations/ThisKeywordRecommenderTests.cs
+++ b/src/EditorFeatures/CSharpTest2/Recommendations/ThisKeywordRecommenderTests.cs
@@ -342,6 +342,230 @@ void nested()
 }");
         }
 
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInAnonymousMethod()
+        {
+            await VerifyKeywordAsync(
+@"class C
+{
+    int Method()
+    {
+        Action a = delegate
+        {
+            $$
+        };
+    }
+}");
+        }
+
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedAnonymousMethod()
+        {
+            await VerifyKeywordAsync(
+@"class C
+{
+    int Method()
+    {
+        Action a = delegate
+        {
+            Action b = delegate
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInAnonymousMethodInStaticMethod()
+        {
+            await VerifyAbsenceAsync(
+@"class C
+{
+    static int Method()
+    {
+        Action a = delegate
+        {
+            $$
+        };
+    }
+}");
+        }
+
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedAnonymousMethodInStaticMethod()
+        {
+            await VerifyAbsenceAsync(
+@"class C
+{
+    static int Method()
+    {
+        Action a = delegate
+        {
+            Action b = delegate
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInLambdaExpression()
+        {
+            await VerifyKeywordAsync(
+@"class C
+{
+    int Method()
+    {
+        Action a = () =>
+        {
+            $$
+        };
+    }
+}");
+        }
+
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedLambdaExpression()
+        {
+            await VerifyKeywordAsync(
+@"class C
+{
+    int Method()
+    {
+        Action a = () =>
+        {
+            Action b = () =>
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInLambdaExpressionInStaticMethod()
+        {
+            await VerifyAbsenceAsync(
+@"class C
+{
+    static int Method()
+    {
+        Action a = () =>
+        {
+            $$
+        };
+    }
+}");
+        }
+
+        [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedLambdaExpressionInStaticMethod()
+        {
+            await VerifyAbsenceAsync(
+@"class C
+{
+    static int Method()
+    {
+        Action a = () =>
+        {
+            Action b = () =>
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedLambdaExpressionInAnonymousMethod()
+        {
+            await VerifyKeywordAsync(
+@"class C
+{
+    int Method()
+    {
+        Action a = delegate
+        {
+            Action b = () =>
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedAnonymousInLambdaExpression()
+        {
+            await VerifyKeywordAsync(
+@"class C
+{
+    int Method()
+    {
+        Action a = () =>
+        {
+            Action b = delegate
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedAnonymousMethodInLambdaExpressionInStaticMethod()
+        {
+            await VerifyAbsenceAsync(
+@"class C
+{
+    static int Method()
+    {
+        Action a = () =>
+        {
+            Action b = delegate
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
+        [WorkItem(27923, "https://github.com/dotnet/roslyn/issues/27923")]
+        public async Task TestInNestedLambdaExpressionInAnonymousMethodInStaticMethod()
+        {
+            await VerifyAbsenceAsync(
+@"class C
+{
+    static int Method()
+    {
+        Action a = delegate
+        {
+            Action b = () =>
+            {
+                $$
+            };
+        };
+    }
+}");
+        }
+
         [Fact, Trait(Traits.Feature, Traits.Features.KeywordRecommending)]
         public async Task TestAfterAttribute()
         {
diff --git a/src/Workspaces/CSharp/Portable/Extensions/ContextQuery/SyntaxTreeExtensions.cs b/src/Workspaces/CSharp/Portable/Extensions/ContextQuery/SyntaxTreeExtensions.cs
index cc1497d8d8dae03a211fd8fc87bc2003c7a5ac53..23b71f220601dc322b3a18e19dd62485e925a7b0 100644
--- a/src/Workspaces/CSharp/Portable/Extensions/ContextQuery/SyntaxTreeExtensions.cs
+++ b/src/Workspaces/CSharp/Portable/Extensions/ContextQuery/SyntaxTreeExtensions.cs
@@ -1772,7 +1772,7 @@ public static bool IsInstanceContext(this SyntaxTree syntaxTree, SyntaxToken tar
 
             var enclosingSymbol = semanticModel.GetEnclosingSymbol(targetToken.SpanStart, cancellationToken);
 
-            while (enclosingSymbol is IMethodSymbol method && method.MethodKind == MethodKind.LocalFunction)
+            while (enclosingSymbol is IMethodSymbol method && (method.MethodKind == MethodKind.LocalFunction || method.MethodKind == MethodKind.AnonymousFunction))
             {
                 // It is allowed to reference the instance (`this`) within a local function, as long as the containing method allows it
                 enclosingSymbol = method.ContainingSymbol;