diff --git a/Src/FluentAssertions/AssertionExtensions.cs b/Src/FluentAssertions/AssertionExtensions.cs
index aa0b65309a..9a571bc755 100644
--- a/Src/FluentAssertions/AssertionExtensions.cs
+++ b/Src/FluentAssertions/AssertionExtensions.cs
@@ -1028,6 +1028,22 @@ public static void Should(this TypeSelectorAssertions _)
             InvalidShouldCall();
         }
 
+        /// <inheritdoc cref="Should(ExecutionTimeAssertions)" />
+        [Obsolete("You are asserting the 'AndConstraint' itself. Remove the 'Should()' method directly following 'And'", error: true)]
+        public static void Should<TAssertions>(this DateTimeRangeAssertions<TAssertions> _)
+            where TAssertions : DateTimeAssertions<TAssertions>
+        {
+            InvalidShouldCall();
+        }
+
+        /// <inheritdoc cref="Should(ExecutionTimeAssertions)" />
+        [Obsolete("You are asserting the 'AndConstraint' itself. Remove the 'Should()' method directly following 'And'", error: true)]
+        public static void Should<TAssertions>(this DateTimeOffsetRangeAssertions<TAssertions> _)
+            where TAssertions : DateTimeOffsetAssertions<TAssertions>
+        {
+            InvalidShouldCall();
+        }
+
         [DoesNotReturn]
         private static void InvalidShouldCall()
         {
diff --git a/Tests/FluentAssertions.Specs/AssertionExtensionsSpecs.cs b/Tests/FluentAssertions.Specs/AssertionExtensionsSpecs.cs
index e9f4bb26a5..288f92eb2f 100644
--- a/Tests/FluentAssertions.Specs/AssertionExtensionsSpecs.cs
+++ b/Tests/FluentAssertions.Specs/AssertionExtensionsSpecs.cs
@@ -39,7 +39,9 @@ private static bool OverridesEquals(Type t)
         [InlineData(typeof(ReferenceTypeAssertions<object, ObjectAssertions>))]
         [InlineData(typeof(BooleanAssertions<BooleanAssertions>))]
         [InlineData(typeof(DateTimeAssertions<DateTimeAssertions>))]
+        [InlineData(typeof(DateTimeRangeAssertions<DateTimeAssertions>))]
         [InlineData(typeof(DateTimeOffsetAssertions<DateTimeOffsetAssertions>))]
+        [InlineData(typeof(DateTimeOffsetRangeAssertions<DateTimeOffsetAssertions>))]
 #if NET6_0_OR_GREATER
         [InlineData(typeof(DateOnlyAssertions<DateOnlyAssertions>))]
         [InlineData(typeof(TimeOnlyAssertions<TimeOnlyAssertions>))]
@@ -95,6 +97,11 @@ public void Should_methods_have_a_matching_overload_to_guard_against_chaining_an
                 .Where(m => !IsGuardOverload(m))
                 .Select(t => GetMostParentType(t.ReturnType))
                 .Distinct()
+                .Concat(new[]
+                {
+                    typeof(DateTimeRangeAssertions<>),
+                    typeof(DateTimeOffsetRangeAssertions<>)
+                })
                 .ToList();
 
             List<Type> fakeOverloads = shouldOverloads