diff --git a/TUnit.Assertions.SourceGenerator/Generators/AssertionMethodGenerator.cs b/TUnit.Assertions.SourceGenerator/Generators/AssertionMethodGenerator.cs
index d2c023ea00..1120d2c753 100644
--- a/TUnit.Assertions.SourceGenerator/Generators/AssertionMethodGenerator.cs
+++ b/TUnit.Assertions.SourceGenerator/Generators/AssertionMethodGenerator.cs
@@ -699,7 +699,28 @@ private static void GenerateAssertConditionClassForMethod(SourceProductionContex
             sourceBuilder.AppendLine();
         }
 
-        if (!attributeData.TargetType.IsValueType)
+        // Check if the method's first parameter accepts null values
+        // For static methods like string.IsNullOrEmpty(string? value), the first parameter
+        // is the value being asserted. If it's marked as nullable (NullableAnnotation.Annotated),
+        // we should skip the null check and let the method handle null values.
+        var shouldGenerateNullCheck = !attributeData.TargetType.IsValueType;
+        if (shouldGenerateNullCheck && staticMethod.Parameters.Length > 0)
+        {
+            var firstParameter = staticMethod.Parameters[0];
+            // Skip null check if the parameter explicitly accepts null (e.g., string? value)
+            if (firstParameter.NullableAnnotation == NullableAnnotation.Annotated)
+            {
+                shouldGenerateNullCheck = false;
+            }
+            // For backwards compatibility with .NET Framework where NullableAnnotation might not be set,
+            // also check for well-known methods that accept null by design
+            else if (methodName == "IsNullOrEmpty" || methodName == "IsNullOrWhiteSpace")
+            {
+                shouldGenerateNullCheck = false;
+            }
+        }
+
+        if (shouldGenerateNullCheck)
         {
             sourceBuilder.AppendLine("        if (actualValue is null)");
             sourceBuilder.AppendLine("        {");
diff --git a/TUnit.Assertions.Tests/StringNullabilityAssertionTests.cs b/TUnit.Assertions.Tests/StringNullabilityAssertionTests.cs
new file mode 100644
index 0000000000..45c7b48969
--- /dev/null
+++ b/TUnit.Assertions.Tests/StringNullabilityAssertionTests.cs
@@ -0,0 +1,91 @@
+using TUnit.Assertions.Extensions;
+
+namespace TUnit.Assertions.Tests;
+
+/// <summary>
+/// Tests for string assertions that accept null values (IsNullOrEmpty, IsNullOrWhiteSpace)
+/// </summary>
+public class StringNullabilityAssertionTests
+{
+    [Test]
+    public async Task IsNullOrEmpty_WithNullString_Passes()
+    {
+        string? nullString = null;
+        await Assert.That(nullString).IsNullOrEmpty();
+    }
+
+    [Test]
+    public async Task IsNullOrEmpty_WithEmptyString_Passes()
+    {
+        var emptyString = "";
+        await Assert.That(emptyString).IsNullOrEmpty();
+    }
+
+    [Test]
+    public async Task IsNullOrEmpty_WithNonEmptyString_Fails()
+    {
+        var value = "Hello";
+        await Assert.That(async () => await Assert.That(value).IsNullOrEmpty())
+            .Throws<AssertionException>();
+    }
+
+    [Test]
+    public async Task IsNullOrEmpty_WithWhitespace_Fails()
+    {
+        var value = " ";
+        await Assert.That(async () => await Assert.That(value).IsNullOrEmpty())
+            .Throws<AssertionException>();
+    }
+
+    [Test]
+    public async Task IsNullOrWhiteSpace_WithNullString_Passes()
+    {
+        string? nullString = null;
+        await Assert.That(nullString).IsNullOrWhiteSpace();
+    }
+
+    [Test]
+    public async Task IsNullOrWhiteSpace_WithEmptyString_Passes()
+    {
+        var emptyString = "";
+        await Assert.That(emptyString).IsNullOrWhiteSpace();
+    }
+
+    [Test]
+    public async Task IsNullOrWhiteSpace_WithWhitespace_Passes()
+    {
+        var whitespace = "   ";
+        await Assert.That(whitespace).IsNullOrWhiteSpace();
+    }
+
+    [Test]
+    public async Task IsNullOrWhiteSpace_WithNonEmptyString_Fails()
+    {
+        var value = "Hello";
+        await Assert.That(async () => await Assert.That(value).IsNullOrWhiteSpace())
+            .Throws<AssertionException>();
+    }
+
+    [Test]
+    public async Task IsNotNullOrEmpty_WithNullString_Fails()
+    {
+        string? nullString = null;
+        await Assert.That(async () => await Assert.That(nullString).IsNotNullOrEmpty())
+            .Throws<AssertionException>();
+    }
+
+    [Test]
+    public async Task IsNotNullOrEmpty_WithEmptyString_Fails()
+    {
+        var emptyString = "";
+        await Assert.That(async () => await Assert.That(emptyString).IsNotNullOrEmpty())
+            .Throws<AssertionException>();
+    }
+
+    [Test]
+    public async Task IsNotNullOrEmpty_WithNonEmptyString_Passes()
+    {
+        var value = "Hello";
+        await Assert.That(value).IsNotNullOrEmpty();
+    }
+}