diff --git a/src/Spectre.Console.Tests/Unit/Prompts/TextPromptTests.cs b/src/Spectre.Console.Tests/Unit/Prompts/TextPromptTests.cs
index 09d0eb983..d2646a8db 100644
--- a/src/Spectre.Console.Tests/Unit/Prompts/TextPromptTests.cs
+++ b/src/Spectre.Console.Tests/Unit/Prompts/TextPromptTests.cs
@@ -489,4 +489,256 @@ public async Task Uses_case_insensitive_comparison_when_no_comparer_is_passed(st
         // Then
         result.ShouldBe("Yes");
     }
+
+    [Fact]
+    public void Validate_BoolOverload_ShortCircuits()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")
+            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a");
+            }, "missing a");
+
+        // When
+        var result = prompt.Validator?.Invoke("ab");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Error("too short"));
+        secondInvoked.ShouldBeFalse();
+    }
+
+    [Fact]
+    public void Validate_BoolOverload_Returns_Chained_Validation_Error()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")
+            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a");
+            }, "missing a");
+
+        // When
+        var result = prompt.Validator?.Invoke("bbc");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Error("missing a"));
+        secondInvoked.ShouldBeTrue();
+    }
+
+    [Fact]
+    public void Validate_BoolOverload_Returns_Success_When_All_Validators_Pass()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")
+            .Validate(s => s.Contains("a"), "missing a");
+
+        // When
+        var result = prompt.Validator?.Invoke("abc");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Success());
+    }
+
+    [Fact]
+    public void Validate_FuncOverload_ShortCircuits()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+
+        prompt
+            .Validate(s => s.Length < 3 ? ValidationResult.Error("too short") : ValidationResult.Success())
+            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a") ? ValidationResult.Success() : ValidationResult.Error("missing a");
+            } );
+
+        // When
+        var result = prompt.Validator?.Invoke("ab");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Error("too short"));
+        secondInvoked.ShouldBeFalse();
+    }
+
+    [Fact]
+    public void Validate_FuncOverload_Returns_Chained_Validation_Error()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+
+        prompt
+            .Validate(s => s.Length < 3 ? ValidationResult.Error("too short") : ValidationResult.Success())
+            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a") ? ValidationResult.Success() : ValidationResult.Error("missing a");
+            } );
+
+        // When
+        var result = prompt.Validator?.Invoke("bbc");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Error("missing a"));
+        secondInvoked.ShouldBeTrue();
+    }
+
+    [Fact]
+    public void Validate_FuncOverload_Returns_Success_When_All_Validators_Pass()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+
+        prompt
+            .Validate(s => s.Length < 3 ? ValidationResult.Error("too short") : ValidationResult.Success())
+            .Validate(s => s.Contains("a") ? ValidationResult.Success() : ValidationResult.Error("missing a") );
+
+        // When
+        var result = prompt.Validator?.Invoke("abc");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Success());
+    }
+
+    [Fact]
+    public void Validate_MixedOverloads_ShortCircuits()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a") ? ValidationResult.Success() : ValidationResult.Error("missing a");
+            } );
+
+        // When
+        var result = prompt.Validator?.Invoke("ab");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Error("too short"));
+        secondInvoked.ShouldBeFalse();
+    }
+
+    [Fact]
+    public void Validate_MixedOverloads_Returns_Chained_Validation_Error()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")
+            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a") ? ValidationResult.Success() : ValidationResult.Error("missing a");
+            } );
+
+        // When
+        var result = prompt.Validator?.Invoke("bbc");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Error("missing a"));
+        secondInvoked.ShouldBeTrue();
+    }
+
+    [Fact]
+    public void Validate_MixedOverloads_Returns_Success_When_All_Validators_Pass()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")
+            .Validate(s => s.Contains("a") ? ValidationResult.Success() : ValidationResult.Error("missing a") );
+
+        // When
+        var result = prompt.Validator?.Invoke("abc");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Success());
+    }
+
+    [Fact]
+    public void Validate_MixedOverloads_WithThreeValidators_Returns_ThirdValidationError()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+        var thirdInvoked = false;
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")
+            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a")
+                    ? ValidationResult.Success()
+                    : ValidationResult.Error("missing a");
+            })
+            .Validate(s =>
+            {
+                thirdInvoked = true;
+                return s.EndsWith("z");
+            }, "must end with z");
+
+        // When
+        var result = prompt.Validator?.Invoke("abc");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Error("must end with z"));
+        secondInvoked.ShouldBeTrue();
+        thirdInvoked.ShouldBeTrue();
+    }
+
+    [Fact]
+    public void Validate_MixedOverloads_WithThreeValidators_Returns_Success_When_All_Validators_Pass()
+    {
+        // Given
+        var prompt = new TextPrompt<string>("Enter:");
+        var secondInvoked = false;
+        var thirdInvoked = false;
+
+        prompt
+            .Validate(s => s.Length >= 3, "too short")
+            .Validate(s =>
+            {
+                secondInvoked = true;
+                return s.Contains("a")
+                    ? ValidationResult.Success()
+                    : ValidationResult.Error("missing a");
+            })
+            .Validate(s =>
+            {
+                thirdInvoked = true;
+                return s.EndsWith("z");
+            }, "must end with z");
+
+        // When
+        var result = prompt.Validator?.Invoke("abz");
+
+        // Then
+        result.ShouldBeEquivalentTo(ValidationResult.Success());
+        secondInvoked.ShouldBeTrue();
+        thirdInvoked.ShouldBeTrue();
+    }
 }
\ No newline at end of file
diff --git a/src/Spectre.Console/Prompts/TextPromptExtensions.cs b/src/Spectre.Console/Prompts/TextPromptExtensions.cs
index e0e9c4662..bb67f36ce 100644
--- a/src/Spectre.Console/Prompts/TextPromptExtensions.cs
+++ b/src/Spectre.Console/Prompts/TextPromptExtensions.cs
@@ -178,9 +178,20 @@ public static TextPrompt<T> DefaultValue<T>(this TextPrompt<T> obj, T value)
     public static TextPrompt<T> Validate<T>(this TextPrompt<T> obj, Func<T, bool> validator, string? message = null)
     {
         ArgumentNullException.ThrowIfNull(obj);
+        ArgumentNullException.ThrowIfNull(validator);
 
+        var previous = obj.Validator;
         obj.Validator = result =>
         {
+            if (previous is not null)
+            {
+                var previousResult = previous(result);
+                if (!previousResult.Successful)
+                {
+                    return previousResult;
+                }
+            }
+
             if (validator(result))
             {
                 return ValidationResult.Success();
@@ -202,8 +213,23 @@ public static TextPrompt<T> Validate<T>(this TextPrompt<T> obj, Func<T, bool> va
     public static TextPrompt<T> Validate<T>(this TextPrompt<T> obj, Func<T, ValidationResult> validator)
     {
         ArgumentNullException.ThrowIfNull(obj);
+        ArgumentNullException.ThrowIfNull(validator);
+
+        var previous = obj.Validator;
+
+        obj.Validator = result =>
+        {
+            if (previous is not null)
+            {
+                var previousResult = previous(result);
+                if (!previousResult.Successful)
+                {
+                    return previousResult;
+                }
+            }
 
-        obj.Validator = validator;
+            return validator(result);
+        };
 
         return obj;
     }