diff --git a/src/Microsoft.AspNetCore.Mvc.ViewFeatures/ViewFeatures/HtmlHelperOfT.cs b/src/Microsoft.AspNetCore.Mvc.ViewFeatures/ViewFeatures/HtmlHelperOfT.cs
index bb61b5867d..833a271740 100644
--- a/src/Microsoft.AspNetCore.Mvc.ViewFeatures/ViewFeatures/HtmlHelperOfT.cs
+++ b/src/Microsoft.AspNetCore.Mvc.ViewFeatures/ViewFeatures/HtmlHelperOfT.cs
@@ -63,6 +63,22 @@ namespace Microsoft.AspNetCore.Mvc.ViewFeatures
             }
 
             ViewData = viewContext.ViewData as ViewDataDictionary<TModel>;
+
+            if (ViewData == null)
+            {
+                // The view data that we have at this point might be of a more derived type than the one defined at compile time.
+                // For example ViewDataDictionary<Derived> where our TModel is Base and Derived : Base.
+                // This can't happen for regular views, but it can happen in razor pages if someone modified the model type through
+                // the page application model.
+                // In that case, we check if the type of the current view data, 'ViewDataDictionary<TRuntime>' is "covariant" with the
+                // one defined at compile time 'ViewDataDictionary<TCompile>'
+                var runtimeType = viewContext.ViewData.ModelMetadata.ModelType;
+                if (runtimeType != null && typeof(TModel) != runtimeType && typeof(TModel).IsAssignableFrom(runtimeType))
+                {
+                    ViewData = new ViewDataDictionary<TModel>(viewContext.ViewData, viewContext.ViewData.Model);
+                }
+            }
+
             if (ViewData == null)
             {
                 // viewContext may contain a base ViewDataDictionary instance. So complain about that type, not TModel.
diff --git a/test/Microsoft.AspNetCore.Mvc.ViewFeatures.Test/Rendering/HtmlHelperTest.cs b/test/Microsoft.AspNetCore.Mvc.ViewFeatures.Test/Rendering/HtmlHelperTest.cs
index 180dea3415..29ffb589d8 100644
--- a/test/Microsoft.AspNetCore.Mvc.ViewFeatures.Test/Rendering/HtmlHelperTest.cs
+++ b/test/Microsoft.AspNetCore.Mvc.ViewFeatures.Test/Rendering/HtmlHelperTest.cs
@@ -1,6 +1,7 @@
 // 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.
 
+using System;
 using System.Collections.Generic;
 using Microsoft.AspNetCore.Mvc.ViewFeatures;
 using Xunit;
@@ -286,6 +287,81 @@ namespace Microsoft.AspNetCore.Mvc.Rendering
             Assert.Equal(expectedString, result.ToString());
         }
 
+        [Fact]
+        public void Contextualize_WorksWithCovariantViewDataDictionary()
+        {
+            // Arrange
+            var helperToContextualize = DefaultTemplatesUtilities
+                .GetHtmlHelper<BaseModel>(model: null);
+
+            var viewContext = DefaultTemplatesUtilities
+                .GetHtmlHelper<DerivedModel>(model: null)
+                .ViewContext;
+
+            // Act
+            helperToContextualize.Contextualize(viewContext);
+
+            // Assert
+            Assert.IsType<ViewDataDictionary<BaseModel>>(
+                helperToContextualize.ViewData);
+
+            Assert.Same(helperToContextualize.ViewContext, viewContext);
+        }
+
+        [Fact]
+        public void Contextualize_ThrowsIfViewDataDictionariesAreNotCompatible()
+        {
+            // Arrange
+            var helperToContextualize = DefaultTemplatesUtilities
+                .GetHtmlHelper<BaseModel>(model: null);
+
+            var viewContext = DefaultTemplatesUtilities
+                .GetHtmlHelper<NonDerivedModel>(model: null)
+                .ViewContext;
+
+            var expectedMessage = $"Property '{nameof(ViewContext.ViewData)}' is of type " +
+                $"'{typeof(ViewDataDictionary<NonDerivedModel>).FullName}'," +
+                $" but this method requires a value of type '{typeof(ViewDataDictionary<BaseModel>).FullName}'.";
+
+            // Act & Assert
+            var exception = Assert.Throws<ArgumentException>("viewContext", () => helperToContextualize.Contextualize(viewContext));
+            Assert.Contains(expectedMessage, exception.Message);
+        }
+
+        [Fact]
+        public void Contextualize_ThrowsForNonGenericViewDataDictionaries()
+        {
+            // Arrange
+            var helperToContextualize = DefaultTemplatesUtilities
+                .GetHtmlHelper<BaseModel>(model: null);
+
+            var viewContext = DefaultTemplatesUtilities
+                .GetHtmlHelper<BaseModel>(model: null)
+                .ViewContext;
+            viewContext.ViewData = new ViewDataDictionary(viewContext.ViewData);
+
+            var expectedMessage = $"Property '{nameof(ViewContext.ViewData)}' is of type " +
+                $"'{typeof(ViewDataDictionary).FullName}'," +
+                $" but this method requires a value of type '{typeof(ViewDataDictionary<BaseModel>).FullName}'.";
+
+            // Act & Assert
+            var exception = Assert.Throws<ArgumentException>("viewContext", () => helperToContextualize.Contextualize(viewContext));
+            Assert.Contains(expectedMessage, exception.Message);
+        }
+
+        private class BaseModel
+        {
+            public string Name { get; set; }
+        }
+
+        private class DerivedModel : BaseModel
+        {
+        }
+
+        private class NonDerivedModel
+        {
+        }
+
         [Theory]
         [InlineData("SomeName", "SomeName")]
         [InlineData("Obj1.Prop1", "Obj1_Prop1")]