diff --git a/src/Swashbuckle.AspNetCore.SwaggerGen/SchemaGenerator/MemberInfoExtensions.cs b/src/Swashbuckle.AspNetCore.SwaggerGen/SchemaGenerator/MemberInfoExtensions.cs
index 574c305f32..e376e00b5b 100644
--- a/src/Swashbuckle.AspNetCore.SwaggerGen/SchemaGenerator/MemberInfoExtensions.cs
+++ b/src/Swashbuckle.AspNetCore.SwaggerGen/SchemaGenerator/MemberInfoExtensions.cs
@@ -136,8 +136,8 @@ private static object GetNullableAttribute(this MemberInfo memberInfo)
         private static bool GetNullableFallbackValue(this MemberInfo memberInfo)
         {
             var declaringTypes = memberInfo.DeclaringType.IsNested
-                ? new Type[] { memberInfo.DeclaringType, memberInfo.DeclaringType.DeclaringType }
-                : new Type[] { memberInfo.DeclaringType };
+                ? GetDeclaringTypeChain(memberInfo)
+                : new List<Type>(1) { memberInfo.DeclaringType };
 
             foreach (var declaringType in declaringTypes)
             {
@@ -162,5 +162,19 @@ private static bool GetNullableFallbackValue(this MemberInfo memberInfo)
 
             return false;
         }
+
+        private static List<Type> GetDeclaringTypeChain(MemberInfo memberInfo)
+        {
+            var chain = new List<Type>();
+            var currentType = memberInfo.DeclaringType;
+
+            while (currentType != null)
+            {
+                chain.Add(currentType);
+                currentType = currentType.DeclaringType;
+            }
+
+            return chain;
+        }
     }
 }
diff --git a/test/Swashbuckle.AspNetCore.SwaggerGen.Test/SchemaGenerator/JsonSerializerSchemaGeneratorTests.cs b/test/Swashbuckle.AspNetCore.SwaggerGen.Test/SchemaGenerator/JsonSerializerSchemaGeneratorTests.cs
index 88e20d03f9..7db3a66387 100644
--- a/test/Swashbuckle.AspNetCore.SwaggerGen.Test/SchemaGenerator/JsonSerializerSchemaGeneratorTests.cs
+++ b/test/Swashbuckle.AspNetCore.SwaggerGen.Test/SchemaGenerator/JsonSerializerSchemaGeneratorTests.cs
@@ -981,6 +981,28 @@ public void GenerateSchema_SupportsOption_SuppressImplicitRequiredAttributeForNo
             Assert.Equal(!suppress, propertyIsRequired);
         }
 
+        [Theory]
+        [InlineData(typeof(TypeWithNullableContextAnnotated), nameof(TypeWithNullableContextAnnotated.SubTypeWithNestedSubType.Nested), nameof(TypeWithNullableContextAnnotated.SubTypeWithNestedSubType.Nested.NullableString), true)]
+        [InlineData(typeof(TypeWithNullableContextAnnotated), nameof(TypeWithNullableContextAnnotated.SubTypeWithNestedSubType.Nested), nameof(TypeWithNullableContextAnnotated.SubTypeWithNestedSubType.Nested.NonNullableString), false)]
+        [InlineData(typeof(TypeWithNullableContextNotAnnotated), nameof(TypeWithNullableContextNotAnnotated.SubTypeWithNestedSubType.Nested), nameof(TypeWithNullableContextAnnotated.SubTypeWithNestedSubType.Nested.NullableString), true)]
+        [InlineData(typeof(TypeWithNullableContextNotAnnotated), nameof(TypeWithNullableContextNotAnnotated.SubTypeWithNestedSubType.Nested), nameof(TypeWithNullableContextAnnotated.SubTypeWithNestedSubType.Nested.NonNullableString), false)]
+        public void GenerateSchema_SupportsOption_SupportNonNullableReferenceTypes_NestedWithinNested(
+            Type declaringType,
+            string subType,
+            string propertyName,
+            bool expectedNullable)
+        {
+            var subject = Subject(
+                configureGenerator: c => c.SupportNonNullableReferenceTypes = true
+            );
+            var schemaRepository = new SchemaRepository();
+
+            subject.GenerateSchema(declaringType, schemaRepository);
+
+            var propertySchema = schemaRepository.Schemas[subType].Properties[propertyName];
+            Assert.Equal(expectedNullable, propertySchema.Nullable);
+        }
+
         [Theory]
         [InlineData(typeof(TypeWithNullableContextAnnotated))]
         [InlineData(typeof(TypeWithNullableContextNotAnnotated))]
diff --git a/test/Swashbuckle.AspNetCore.TestSupport/Fixtures/TypeWithNullableContext.cs b/test/Swashbuckle.AspNetCore.TestSupport/Fixtures/TypeWithNullableContext.cs
index 81cf7dcb5c..8d83a01e1f 100644
--- a/test/Swashbuckle.AspNetCore.TestSupport/Fixtures/TypeWithNullableContext.cs
+++ b/test/Swashbuckle.AspNetCore.TestSupport/Fixtures/TypeWithNullableContext.cs
@@ -48,6 +48,7 @@ public class TypeWithNullableContextNotAnnotated
 
         public List<SubTypeWithOneNullableContent>? NullableList { get; set; }
         public List<SubTypeWithOneNonNullableContent> NonNullableList { get; set; } = default!;
+        public SubTypeWithNestedSubType NestedWithNested { get; set; } = default!;
 
         public Dictionary<string, string>? NullableDictionaryInNonNullableContent { get; set; }
         public Dictionary<string, string> NonNullableDictionaryInNonNullableContent { get; set; } = default!;
@@ -88,6 +89,17 @@ public class SubTypeWithOneNonNullableContent
         {
             public string NonNullableString { get; set; } = default!;
         }
+
+        public class SubTypeWithNestedSubType
+        {
+            public Nested NestedProperty { get; set; } = default!;
+
+            public class Nested
+            {
+                public string? NullableString { get; set; }
+                public string NonNullableString { get; set; } = default!;
+            }
+        }
     }
 
     /// <summary>
@@ -128,6 +140,7 @@ public class TypeWithNullableContextAnnotated
 
         public List<SubTypeWithOneNullableContent>? NullableList { get; set; }
         public List<SubTypeWithOneNonNullableContent> NonNullableList { get; set; } = default!;
+        public SubTypeWithNestedSubType NestedWithNested { get; set; } = default!;
 
         public Dictionary<string, string>? NullableDictionaryInNonNullableContent { get; set; }
         public Dictionary<string, string> NonNullableDictionaryInNonNullableContent { get; set; } = default!;
@@ -168,6 +181,17 @@ public class SubTypeWithOneNonNullableContent
         {
             public string NonNullableString { get; set; } = default!;
         }
+
+        public class SubTypeWithNestedSubType
+        {
+            public Nested NestedProperty { get; set; } = default!;
+
+            public class Nested
+            {
+                public string? NullableString { get; set; }
+                public string NonNullableString { get; set; } = default!;
+            }
+        }
     }
 #nullable restore
 }