diff --git a/src/CommunityToolkit.Mvvm.SourceGenerators/CommunityToolkit.Mvvm.SourceGenerators.projitems b/src/CommunityToolkit.Mvvm.SourceGenerators/CommunityToolkit.Mvvm.SourceGenerators.projitems
index f875a91df..9e719e412 100644
--- a/src/CommunityToolkit.Mvvm.SourceGenerators/CommunityToolkit.Mvvm.SourceGenerators.projitems
+++ b/src/CommunityToolkit.Mvvm.SourceGenerators/CommunityToolkit.Mvvm.SourceGenerators.projitems
@@ -74,6 +74,7 @@
     <Compile Include="$(MSBuildThisFileDirectory)Extensions\GeneratorAttributeSyntaxContextWithOptions.cs" />
     <Compile Include="$(MSBuildThisFileDirectory)Extensions\IncrementalGeneratorInitializationContextExtensions.cs" />
     <Compile Include="$(MSBuildThisFileDirectory)Extensions\IncrementalValuesProviderExtensions.cs" />
+    <Compile Include="$(MSBuildThisFileDirectory)Extensions\IMethodSymbolExtensions.cs" />
     <Compile Include="$(MSBuildThisFileDirectory)Extensions\MethodDeclarationSyntaxExtensions.cs" />
     <Compile Include="$(MSBuildThisFileDirectory)Extensions\SymbolInfoExtensions.cs" />
     <Compile Include="$(MSBuildThisFileDirectory)Extensions\ISymbolExtensions.cs" />
diff --git a/src/CommunityToolkit.Mvvm.SourceGenerators/Extensions/IMethodSymbolExtensions.cs b/src/CommunityToolkit.Mvvm.SourceGenerators/Extensions/IMethodSymbolExtensions.cs
new file mode 100644
index 000000000..23f4786d3
--- /dev/null
+++ b/src/CommunityToolkit.Mvvm.SourceGenerators/Extensions/IMethodSymbolExtensions.cs
@@ -0,0 +1,78 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using System.Collections.Immutable;
+using System.Linq;
+using Microsoft.CodeAnalysis;
+
+namespace CommunityToolkit.Mvvm.SourceGenerators.Extensions;
+
+/// <summary>
+/// Extension methods for the <see cref="IMethodSymbol"/> type.
+/// </summary>
+internal static class IMethodSymbolExtensions
+{
+    /// <summary>
+    /// Checks whether all input symbols are <see cref="IMethodSymbol"/>-s in the same override hierarchy.
+    /// </summary>
+    /// <param name="symbols">The input <see cref="ISymbol"/> set to check.</param>
+    /// <returns>Whether all input symbols are <see cref="IMethodSymbol"/>-s in the same override hierarchy.</returns>
+    public static bool AreAllInSameOverriddenMethodHierarchy(this ImmutableArray<ISymbol> symbols)
+    {
+        IMethodSymbol? baseSymbol = null;
+
+        // Look for the base method
+        foreach (ISymbol currentSymbol in symbols)
+        {
+            // If any input symbol is not a method, we can stop right away
+            if (currentSymbol is not IMethodSymbol methodSymbol)
+            {
+                return false;
+            }
+
+            if (methodSymbol.IsVirtual)
+            {
+                // If we already found a base method, all methods can't possibly be in the same hierarchy
+                if (baseSymbol is not null)
+                {
+                    return false;
+                }
+
+                baseSymbol = methodSymbol;
+            }
+        }
+
+        // If we didn't find any, stop here
+        if (baseSymbol is null)
+        {
+            return false;
+        }
+
+        // Verify all methods are in the same tree
+        foreach (ISymbol currentSymbol in symbols)
+        {
+            IMethodSymbol methodSymbol = (IMethodSymbol)currentSymbol;
+
+            // Ignore the base method
+            if (SymbolEqualityComparer.Default.Equals(methodSymbol, baseSymbol))
+            {
+                continue;
+            }
+
+            // If the current method isn't an override, then fail
+            if (methodSymbol.OverriddenMethod is not { } overriddenMethod)
+            {
+                return false;
+            }
+
+            // The current method must be overriding another one in the set
+            if (!symbols.Any(symbol => SymbolEqualityComparer.Default.Equals(symbol, overriddenMethod)))
+            {
+                return false;
+            }
+        }
+
+        return true;
+    }
+}
diff --git a/src/CommunityToolkit.Mvvm.SourceGenerators/Input/RelayCommandGenerator.Execute.cs b/src/CommunityToolkit.Mvvm.SourceGenerators/Input/RelayCommandGenerator.Execute.cs
index d40086135..57eb1ebcf 100644
--- a/src/CommunityToolkit.Mvvm.SourceGenerators/Input/RelayCommandGenerator.Execute.cs
+++ b/src/CommunityToolkit.Mvvm.SourceGenerators/Input/RelayCommandGenerator.Execute.cs
@@ -810,8 +810,10 @@ private static bool TryGetCanExecuteExpressionType(
 
                 diagnostics.Add(InvalidCanExecuteMemberNameError, methodSymbol, memberName, methodSymbol.ContainingType);
             }
-            else if (canExecuteSymbols.Length > 1)
+            else if (canExecuteSymbols.Length > 1 && !canExecuteSymbols.AreAllInSameOverriddenMethodHierarchy())
             {
+                // We specifically allow targeting methods which are overridden: they'll be more than one,
+                // but it doesn't matter since you'd only ever call "one", being the most derived one.
                 diagnostics.Add(MultipleCanExecuteMemberNameMatchesError, methodSymbol, memberName, methodSymbol.ContainingType);
             }
             else if (TryGetCanExecuteExpressionFromSymbol(canExecuteSymbols[0], commandTypeArguments, out canExecuteExpressionType))
diff --git a/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsCodegen.cs b/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsCodegen.cs
index d3d44ec5b..d91dfe2b2 100644
--- a/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsCodegen.cs
+++ b/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsCodegen.cs
@@ -2060,6 +2060,60 @@ partial class MyViewModel
         VerifyGenerateSources(source, new[] { new RelayCommandGenerator() }, ("MyViewModel.Test.g.cs", result));
     }
 
+    [TestMethod]
+    public void RelayCommandWithOverriddenCanExecute_TargetsOverriddenMethod()
+    {
+        string source = """
+            using CommunityToolkit.Mvvm.ComponentModel;
+            using CommunityToolkit.Mvvm.Input;
+
+            namespace MyApp;
+
+            public partial class BaseViewModel : ObservableObject
+            {
+                protected virtual bool CanDoStuff()
+                {
+                    return false;
+                }
+            }
+
+            public partial class SampleViewModel : BaseViewModel
+            {            
+                [RelayCommand(CanExecute = nameof(CanDoStuff)]
+                private void DoStuff()
+                {
+                }
+
+                protected override bool CanDoStuff()
+                {
+                    return true;
+                }
+            }
+            """;
+
+        string result = """
+            // <auto-generated/>
+            #pragma warning disable
+            #nullable enable
+            namespace MyApp
+            {
+                /// <inheritdoc/>
+                partial class SampleViewModel
+                {
+                    /// <summary>The backing field for <see cref="DoStuffCommand"/>.</summary>
+                    [global::System.CodeDom.Compiler.GeneratedCode("CommunityToolkit.Mvvm.SourceGenerators.RelayCommandGenerator", <ASSEMBLY_VERSION>)]
+                    private global::CommunityToolkit.Mvvm.Input.RelayCommand? doStuffCommand;
+                    /// <summary>Gets an <see cref="global::CommunityToolkit.Mvvm.Input.IRelayCommand"/> instance wrapping <see cref="DoStuff"/>.</summary>
+                    [global::System.CodeDom.Compiler.GeneratedCode("CommunityToolkit.Mvvm.SourceGenerators.RelayCommandGenerator", <ASSEMBLY_VERSION>)]
+                    [global::System.Diagnostics.CodeAnalysis.ExcludeFromCodeCoverage]
+                    public global::CommunityToolkit.Mvvm.Input.IRelayCommand DoStuffCommand => doStuffCommand ??= new global::CommunityToolkit.Mvvm.Input.RelayCommand(new global::System.Action(DoStuff), CanDoStuff);
+                }
+            }
+            """;
+
+        VerifyGenerateSources(source, new[] { new RelayCommandGenerator() }, ("MyApp.SampleViewModel.DoStuff.g.cs", result));
+    }
+
     [TestMethod]
     public void ObservableProperty_AnnotatedFieldHasValueIdentifier()
     {
diff --git a/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsDiagnostics.cs b/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsDiagnostics.cs
index cb866377d..f18ff7dfd 100644
--- a/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsDiagnostics.cs
+++ b/tests/CommunityToolkit.Mvvm.SourceGenerators.UnitTests/Test_SourceGeneratorsDiagnostics.cs
@@ -2259,6 +2259,80 @@ await CSharpAnalyzerWithLanguageVersionTest<WinRTRelayCommandIsNotGeneratedBinda
             editorconfig: [("_MvvmToolkitIsUsingWindowsRuntimePack", true)]);
     }
 
+    [TestMethod]
+    public void RelayCommandWithOverriddenCanExecute_DoesNotWarn()
+    {
+        const string source = """
+            using CommunityToolkit.Mvvm.ComponentModel;
+            using CommunityToolkit.Mvvm.Input;
+            
+            namespace MyApp
+            {
+                public partial class BaseViewModel : ObservableObject
+                {
+                    protected virtual bool CanDoStuff()
+                    {
+                        return false;
+                    }
+                }
+
+                public partial class SampleViewModel : BaseViewModel
+                {            
+                    [RelayCommand(CanExecute = nameof(CanDoStuff))]
+                    private void DoStuff()
+                    {
+                    }
+
+                    protected override bool CanDoStuff()
+                    {
+                        return true;
+                    }
+                }
+            }
+            """;
+
+        VerifyGeneratedDiagnostics<RelayCommandGenerator>(source, LanguageVersion.CSharp12);
+    }
+
+    [TestMethod]
+    public void RelayCommandWithOverriddenCanExecute_WithOneMethodNotInTheSameHierarchy_Warns()
+    {
+        const string source = """
+            using CommunityToolkit.Mvvm.ComponentModel;
+            using CommunityToolkit.Mvvm.Input;
+            
+            namespace MyApp
+            {
+                public partial class BaseViewModel : ObservableObject
+                {
+                    protected virtual bool CanDoStuff()
+                    {
+                        return false;
+                    }
+
+                    protected bool CanDoStuff(string x)
+                    {
+                    }
+                }
+
+                public partial class SampleViewModel : BaseViewModel
+                {            
+                    [RelayCommand(CanExecute = nameof(CanDoStuff)]
+                    private void DoStuff()
+                    {
+                    }
+
+                    private override bool CanDoStuff()
+                    {
+                        return true;
+                    }
+                }
+            }
+            """;
+
+        VerifyGeneratedDiagnostics<RelayCommandGenerator>(source, "MVVMTK0010");
+    }
+
     [TestMethod]
     public async Task WinRTClassUsingNotifyPropertyChangedAttributesAnalyzer_NotTargetingWindows_DoesNotWarn()
     {
@@ -2451,10 +2525,23 @@ internal static async Task VerifyAnalyzerDiagnosticsAndSuccessfulGeneration<TAna
     /// <param name="diagnosticsIds">The diagnostic ids to expect for the input source code.</param>
     internal static void VerifyGeneratedDiagnostics<TGenerator>(string source, params string[] diagnosticsIds)
         where TGenerator : class, IIncrementalGenerator, new()
+    {
+        VerifyGeneratedDiagnostics<TGenerator>(source, LanguageVersion.CSharp8, diagnosticsIds);
+    }
+
+    /// <summary>
+    /// Verifies the output of a source generator.
+    /// </summary>
+    /// <typeparam name="TGenerator">The generator type to use.</typeparam>
+    /// <param name="source">The input source to process.</param>
+    /// <param name="languageVersion">The language version to use to parse code and run tests.</param>
+    /// <param name="diagnosticsIds">The diagnostic ids to expect for the input source code.</param>
+    internal static void VerifyGeneratedDiagnostics<TGenerator>(string source, LanguageVersion languageVersion, params string[] diagnosticsIds)
+        where TGenerator : class, IIncrementalGenerator, new()
     {
         IIncrementalGenerator generator = new TGenerator();
 
-        VerifyGeneratedDiagnostics(CSharpSyntaxTree.ParseText(source, CSharpParseOptions.Default.WithLanguageVersion(LanguageVersion.CSharp8)), new[] { generator }, diagnosticsIds, []);
+        VerifyGeneratedDiagnostics(CSharpSyntaxTree.ParseText(source, CSharpParseOptions.Default.WithLanguageVersion(languageVersion)), new[] { generator }, diagnosticsIds, []);
     }
 
     /// <summary>