diff --git a/TUnit.Assertions/Assertions/Enums/EnumAssertions.cs b/TUnit.Assertions/Assertions/Enums/EnumAssertions.cs
index 441a1073be..ca5d001106 100644
--- a/TUnit.Assertions/Assertions/Enums/EnumAssertions.cs
+++ b/TUnit.Assertions/Assertions/Enums/EnumAssertions.cs
@@ -22,7 +22,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TEnum> me
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception));
         }
 
 #if NET
@@ -59,7 +59,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TEnum> me
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception));
         }
 
 #if NET
diff --git a/TUnit.Assertions/Assertions/Regex/GroupAssertion.cs b/TUnit.Assertions/Assertions/Regex/GroupAssertion.cs
index b2b998ea6e..35f47e4d98 100644
--- a/TUnit.Assertions/Assertions/Regex/GroupAssertion.cs
+++ b/TUnit.Assertions/Assertions/Regex/GroupAssertion.cs
@@ -41,7 +41,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Reg
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception);
         }
 
         if (collection == null || collection.Count == 0)
@@ -58,7 +58,8 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Reg
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed(ex.Message);
+            var groupDesc = _groupName != null ? $"group '{_groupName}'" : $"group {_groupIndex}";
+            return AssertionResult.Failed($"failed to get {groupDesc}: {ex.Message}", ex);
         }
 
         var groupAssertion = new ValueAssertion<string>(groupValue, _groupName ?? $"group {_groupIndex}");
@@ -116,7 +117,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Reg
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception);
         }
 
         if (match == null)
@@ -133,7 +134,8 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Reg
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed(ex.Message);
+            var groupDesc = _groupName != null ? $"group '{_groupName}'" : $"group {_groupIndex}";
+            return AssertionResult.Failed($"failed to get {groupDesc}: {ex.Message}", ex);
         }
 
         var groupAssertion = new ValueAssertion<string>(groupValue, _groupName ?? $"group {_groupIndex}");
diff --git a/TUnit.Assertions/Assertions/Regex/MatchAssertion.cs b/TUnit.Assertions/Assertions/Regex/MatchAssertion.cs
index 41aef69833..4649ccd191 100644
--- a/TUnit.Assertions/Assertions/Regex/MatchAssertion.cs
+++ b/TUnit.Assertions/Assertions/Regex/MatchAssertion.cs
@@ -28,7 +28,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Reg
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception);
         }
 
         if (collection == null)
@@ -49,7 +49,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Reg
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed($"Failed to get match at index {_index}: {ex.Message}");
+            return AssertionResult.Failed($"Failed to get match at index {_index}: {ex.Message}", ex);
         }
 
         var matchAssertion = new ValueAssertion<RegexMatch>(match, $"match at index {_index}");
diff --git a/TUnit.Assertions/Assertions/Regex/MatchIndexAssertion.cs b/TUnit.Assertions/Assertions/Regex/MatchIndexAssertion.cs
index fa6867476f..38c92d0665 100644
--- a/TUnit.Assertions/Assertions/Regex/MatchIndexAssertion.cs
+++ b/TUnit.Assertions/Assertions/Regex/MatchIndexAssertion.cs
@@ -46,9 +46,9 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<RegexMatc
         {
             if (exception is ArgumentOutOfRangeException || exception is InvalidOperationException)
             {
-                return Task.FromResult(AssertionResult.Failed(exception.Message));
+                return Task.FromResult(AssertionResult.Failed(exception.Message, exception));
             }
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // If we have a match, the assertion passed
diff --git a/TUnit.Assertions/Assertions/Strings/ParseAssertions.cs b/TUnit.Assertions/Assertions/Strings/ParseAssertions.cs
index b39dea5aad..b89083e08e 100644
--- a/TUnit.Assertions/Assertions/Strings/ParseAssertions.cs
+++ b/TUnit.Assertions/Assertions/Strings/ParseAssertions.cs
@@ -37,7 +37,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception));
         }
 
         if (value == null)
@@ -141,7 +141,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception));
         }
 
         if (value == null)
diff --git a/TUnit.Assertions/Collections/MemoryAssertions.cs b/TUnit.Assertions/Collections/MemoryAssertions.cs
index 0cbaf3b12a..2c24d2c83e 100644
--- a/TUnit.Assertions/Collections/MemoryAssertions.cs
+++ b/TUnit.Assertions/Collections/MemoryAssertions.cs
@@ -29,7 +29,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -65,7 +65,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -107,7 +107,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -149,7 +149,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -204,7 +204,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -250,7 +250,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -292,7 +292,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -331,7 +331,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -370,7 +370,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -409,7 +409,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -448,7 +448,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -609,7 +609,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TMemory>
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
diff --git a/TUnit.Assertions/Conditions/AsyncEnumerableAssertions.cs b/TUnit.Assertions/Conditions/AsyncEnumerableAssertions.cs
index 5dc50b2980..4767edbd14 100644
--- a/TUnit.Assertions/Conditions/AsyncEnumerableAssertions.cs
+++ b/TUnit.Assertions/Conditions/AsyncEnumerableAssertions.cs
@@ -17,7 +17,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<IAs
     {
         if (metadata.Exception != null)
         {
-            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception);
         }
 
         if (metadata.Value == null)
diff --git a/TUnit.Assertions/Conditions/CollectionAssertions.cs b/TUnit.Assertions/Conditions/CollectionAssertions.cs
index f384b00cad..4344fe22e2 100644
--- a/TUnit.Assertions/Conditions/CollectionAssertions.cs
+++ b/TUnit.Assertions/Conditions/CollectionAssertions.cs
@@ -27,7 +27,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -59,7 +59,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -99,7 +99,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -139,7 +139,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -179,7 +179,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -215,7 +215,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -251,7 +251,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -287,7 +287,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -326,7 +326,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -409,7 +409,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -449,7 +449,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -485,7 +485,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -551,7 +551,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -607,7 +607,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -666,7 +666,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TCo
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}", exception);
         }
 
         if (value == null)
@@ -688,7 +688,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TCo
             }
             catch (Exception ex)
             {
-                return AssertionResult.Failed($"item at index {index} failed assertion: {ex.Message}");
+                return AssertionResult.Failed($"item at index {index} failed assertion: {ex.Message}", ex);
             }
             index++;
         }
@@ -732,7 +732,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TCo
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}", exception);
         }
 
         if (value == null)
@@ -755,7 +755,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TCo
             }
             catch (Exception ex)
             {
-                return AssertionResult.Failed($"item at index {index} (mapped by {_mapperDescription}) failed assertion: {ex.Message}");
+                return AssertionResult.Failed($"item at index {index} (mapped by {_mapperDescription}) failed assertion: {ex.Message}", ex);
             }
             index++;
         }
@@ -784,7 +784,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -817,7 +817,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -860,7 +860,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -922,7 +922,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
diff --git a/TUnit.Assertions/Conditions/CollectionCountSource.cs b/TUnit.Assertions/Conditions/CollectionCountSource.cs
index 547140c5cd..3af8180b8f 100644
--- a/TUnit.Assertions/Conditions/CollectionCountSource.cs
+++ b/TUnit.Assertions/Conditions/CollectionCountSource.cs
@@ -164,7 +164,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TCo
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}", exception);
         }
 
         if (value == null)
@@ -278,7 +278,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TCo
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}", exception);
         }
 
         if (value == null)
diff --git a/TUnit.Assertions/Conditions/CompletesWithinAssertion.cs b/TUnit.Assertions/Conditions/CompletesWithinAssertion.cs
index dd633d68b4..a277369013 100644
--- a/TUnit.Assertions/Conditions/CompletesWithinAssertion.cs
+++ b/TUnit.Assertions/Conditions/CompletesWithinAssertion.cs
@@ -54,7 +54,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<obj
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed($"threw {ex.GetType().FullName}: {ex.Message}");
+            return AssertionResult.Failed($"threw {ex.GetType().FullName}: {ex.Message}", ex);
         }
     }
 
@@ -112,7 +112,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<obj
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed($"threw {ex.GetType().FullName}: {ex.Message}");
+            return AssertionResult.Failed($"threw {ex.GetType().FullName}: {ex.Message}", ex);
         }
     }
 
diff --git a/TUnit.Assertions/Conditions/DictionaryAssertions.cs b/TUnit.Assertions/Conditions/DictionaryAssertions.cs
index b0b7ffeb53..7d8a883fe2 100644
--- a/TUnit.Assertions/Conditions/DictionaryAssertions.cs
+++ b/TUnit.Assertions/Conditions/DictionaryAssertions.cs
@@ -46,7 +46,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -102,7 +102,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -146,7 +146,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -186,7 +186,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -229,7 +229,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -266,7 +266,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -303,7 +303,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -340,7 +340,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -377,7 +377,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
diff --git a/TUnit.Assertions/Conditions/EqualsAssertion.cs b/TUnit.Assertions/Conditions/EqualsAssertion.cs
index 6d8766deda..b2d074ffe6 100644
--- a/TUnit.Assertions/Conditions/EqualsAssertion.cs
+++ b/TUnit.Assertions/Conditions/EqualsAssertion.cs
@@ -78,7 +78,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // Deep comparison with ignored types
diff --git a/TUnit.Assertions/Conditions/EquatableAssertion.cs b/TUnit.Assertions/Conditions/EquatableAssertion.cs
index 88a82106b8..9bb5280811 100644
--- a/TUnit.Assertions/Conditions/EquatableAssertion.cs
+++ b/TUnit.Assertions/Conditions/EquatableAssertion.cs
@@ -29,7 +29,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TActual>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -74,7 +74,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TActual?>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (!value.HasValue)
diff --git a/TUnit.Assertions/Conditions/ExceptionPropertyAssertions.cs b/TUnit.Assertions/Conditions/ExceptionPropertyAssertions.cs
index df9366496e..a92986149e 100644
--- a/TUnit.Assertions/Conditions/ExceptionPropertyAssertions.cs
+++ b/TUnit.Assertions/Conditions/ExceptionPropertyAssertions.cs
@@ -30,7 +30,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
@@ -81,7 +81,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
@@ -127,7 +127,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
@@ -172,7 +172,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
@@ -234,7 +234,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
@@ -288,7 +288,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
@@ -335,7 +335,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
@@ -387,7 +387,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TExceptio
 
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException));
         }
 
         if (exception == null)
diff --git a/TUnit.Assertions/Conditions/FileSystemAssertions.cs b/TUnit.Assertions/Conditions/FileSystemAssertions.cs
index a16f2fc8d3..a81eb8f5a3 100644
--- a/TUnit.Assertions/Conditions/FileSystemAssertions.cs
+++ b/TUnit.Assertions/Conditions/FileSystemAssertions.cs
@@ -22,7 +22,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<Directory
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -64,7 +64,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<Directory
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -107,7 +107,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<FileInfo>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -148,7 +148,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<FileInfo>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
diff --git a/TUnit.Assertions/Conditions/HasDistinctItemsAssertion.cs b/TUnit.Assertions/Conditions/HasDistinctItemsAssertion.cs
index b7a8eb0e45..6d4acdaa49 100644
--- a/TUnit.Assertions/Conditions/HasDistinctItemsAssertion.cs
+++ b/TUnit.Assertions/Conditions/HasDistinctItemsAssertion.cs
@@ -31,7 +31,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
diff --git a/TUnit.Assertions/Conditions/IsEquivalentToAssertion.cs b/TUnit.Assertions/Conditions/IsEquivalentToAssertion.cs
index 18f2fa8ae7..73f8a9681e 100644
--- a/TUnit.Assertions/Conditions/IsEquivalentToAssertion.cs
+++ b/TUnit.Assertions/Conditions/IsEquivalentToAssertion.cs
@@ -60,7 +60,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var comparer = GetComparer();
diff --git a/TUnit.Assertions/Conditions/Json/JsonStringAssertionExtensions.cs b/TUnit.Assertions/Conditions/Json/JsonStringAssertionExtensions.cs
index 6d8a1fb25e..ac93c5fcd9 100644
--- a/TUnit.Assertions/Conditions/Json/JsonStringAssertionExtensions.cs
+++ b/TUnit.Assertions/Conditions/Json/JsonStringAssertionExtensions.cs
@@ -19,7 +19,7 @@ public static AssertionResult IsValidJson(this string value)
         }
         catch (JsonException ex)
         {
-            return AssertionResult.Failed($"is not valid JSON: {ex.Message}");
+            return AssertionResult.Failed($"is not valid JSON: {ex.Message}", ex);
         }
     }
 
@@ -51,7 +51,7 @@ public static AssertionResult IsValidJsonObject(this string value)
         }
         catch (JsonException ex)
         {
-            return AssertionResult.Failed($"is not valid JSON: {ex.Message}");
+            return AssertionResult.Failed($"is not valid JSON: {ex.Message}", ex);
         }
     }
 
@@ -69,7 +69,7 @@ public static AssertionResult IsValidJsonArray(this string value)
         }
         catch (JsonException ex)
         {
-            return AssertionResult.Failed($"is not valid JSON: {ex.Message}");
+            return AssertionResult.Failed($"is not valid JSON: {ex.Message}", ex);
         }
     }
 }
diff --git a/TUnit.Assertions/Conditions/ListAssertions.cs b/TUnit.Assertions/Conditions/ListAssertions.cs
index 0a7b0e9d6f..904de2ad88 100644
--- a/TUnit.Assertions/Conditions/ListAssertions.cs
+++ b/TUnit.Assertions/Conditions/ListAssertions.cs
@@ -29,7 +29,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -315,7 +315,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -376,7 +376,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -436,7 +436,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
     {
         if (metadata.Exception != null)
         {
-            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception);
         }
 
         if (metadata.Value == null)
@@ -463,7 +463,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
             }
             catch (Exception ex)
             {
-                return AssertionResult.Failed($"item at index {_index} did not satisfy assertion: {ex.Message}");
+                return AssertionResult.Failed($"item at index {_index} did not satisfy assertion: {ex.Message}", ex);
             }
         }
 
@@ -496,7 +496,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -553,7 +553,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -609,7 +609,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
     {
         if (metadata.Exception != null)
         {
-            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception);
         }
 
         if (metadata.Value == null)
@@ -635,7 +635,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
             }
             catch (Exception ex)
             {
-                return AssertionResult.Failed($"last item did not satisfy assertion: {ex.Message}");
+                return AssertionResult.Failed($"last item did not satisfy assertion: {ex.Message}", ex);
             }
         }
 
diff --git a/TUnit.Assertions/Conditions/MappedSatisfiesAssertion.cs b/TUnit.Assertions/Conditions/MappedSatisfiesAssertion.cs
index fa8494c247..fa386a2700 100644
--- a/TUnit.Assertions/Conditions/MappedSatisfiesAssertion.cs
+++ b/TUnit.Assertions/Conditions/MappedSatisfiesAssertion.cs
@@ -36,7 +36,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TVa
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}", exception);
         }
 
         // Map the value
@@ -47,7 +47,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TVa
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed($"selector threw {ex.GetType().Name}: {ex.Message}");
+            return AssertionResult.Failed($"selector threw {ex.GetType().Name}: {ex.Message}", ex);
         }
 
         // Create an assertion for the mapped value
@@ -65,7 +65,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TVa
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed($"mapped value did not satisfy assertions: {ex.Message}");
+            return AssertionResult.Failed($"mapped value did not satisfy assertions: {ex.Message}", ex);
         }
     }
 
@@ -103,7 +103,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TVa
 
         if (exception != null)
         {
-            return AssertionResult.Failed($"threw {exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {exception.GetType().Name}", exception);
         }
 
         // Map the value asynchronously
@@ -114,7 +114,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TVa
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed($"selector threw {ex.GetType().Name}: {ex.Message}");
+            return AssertionResult.Failed($"selector threw {ex.GetType().Name}: {ex.Message}", ex);
         }
 
         // Create an assertion for the mapped value
@@ -132,7 +132,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TVa
         }
         catch (Exception ex)
         {
-            return AssertionResult.Failed($"mapped value did not satisfy assertions: {ex.Message}");
+            return AssertionResult.Failed($"mapped value did not satisfy assertions: {ex.Message}", ex);
         }
     }
 
diff --git a/TUnit.Assertions/Conditions/MutableDictionaryAssertions.cs b/TUnit.Assertions/Conditions/MutableDictionaryAssertions.cs
index 967079cccc..1550aa5d30 100644
--- a/TUnit.Assertions/Conditions/MutableDictionaryAssertions.cs
+++ b/TUnit.Assertions/Conditions/MutableDictionaryAssertions.cs
@@ -39,7 +39,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -87,7 +87,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -125,7 +125,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -167,7 +167,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -211,7 +211,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -255,7 +255,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -296,7 +296,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -337,7 +337,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -378,7 +378,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TDictiona
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
diff --git a/TUnit.Assertions/Conditions/NotEqualsAssertion.cs b/TUnit.Assertions/Conditions/NotEqualsAssertion.cs
index 3009296539..e604dff8db 100644
--- a/TUnit.Assertions/Conditions/NotEqualsAssertion.cs
+++ b/TUnit.Assertions/Conditions/NotEqualsAssertion.cs
@@ -55,7 +55,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // Deep comparison with ignored types
diff --git a/TUnit.Assertions/Conditions/NotEquivalentToAssertion.cs b/TUnit.Assertions/Conditions/NotEquivalentToAssertion.cs
index 41a6d3d880..49594adea0 100644
--- a/TUnit.Assertions/Conditions/NotEquivalentToAssertion.cs
+++ b/TUnit.Assertions/Conditions/NotEquivalentToAssertion.cs
@@ -59,7 +59,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TCollecti
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var comparer = GetComparer();
diff --git a/TUnit.Assertions/Conditions/NotStructuralEquivalencyAssertion.cs b/TUnit.Assertions/Conditions/NotStructuralEquivalencyAssertion.cs
index b3ae71f028..b03d1491dd 100644
--- a/TUnit.Assertions/Conditions/NotStructuralEquivalencyAssertion.cs
+++ b/TUnit.Assertions/Conditions/NotStructuralEquivalencyAssertion.cs
@@ -72,7 +72,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception));
         }
 
         // Create a temporary StructuralEquivalencyAssertion to reuse the comparison logic
diff --git a/TUnit.Assertions/Conditions/NullAssertion.cs b/TUnit.Assertions/Conditions/NullAssertion.cs
index a098e53c59..2a6c15a742 100644
--- a/TUnit.Assertions/Conditions/NullAssertion.cs
+++ b/TUnit.Assertions/Conditions/NullAssertion.cs
@@ -67,7 +67,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (EqualityComparer<TValue>.Default.Equals(value!, default!))
@@ -100,7 +100,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (!EqualityComparer<TValue>.Default.Equals(value!, default!))
@@ -134,7 +134,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue?>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (!value.HasValue)
@@ -168,7 +168,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue?>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value.HasValue)
@@ -202,7 +202,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (EqualityComparer<TValue>.Default.Equals(value!, default!))
@@ -236,7 +236,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (!EqualityComparer<TValue>.Default.Equals(value!, default!))
diff --git a/TUnit.Assertions/Conditions/NumericIsCloseToAssertion.cs b/TUnit.Assertions/Conditions/NumericIsCloseToAssertion.cs
index d6b0dafb8c..0062380ae7 100644
--- a/TUnit.Assertions/Conditions/NumericIsCloseToAssertion.cs
+++ b/TUnit.Assertions/Conditions/NumericIsCloseToAssertion.cs
@@ -41,7 +41,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<double> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // Handle NaN comparisons
@@ -114,7 +114,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<float> me
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // Handle NaN comparisons
@@ -185,7 +185,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<int> meta
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var diff = Math.Abs((long)value - _expected);
@@ -231,7 +231,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<long> met
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var diff = Math.Abs((decimal) value - _expected);
@@ -275,7 +275,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<decimal>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var diff = Math.Abs(value - _expected);
diff --git a/TUnit.Assertions/Conditions/NumericIsWithinPercentOfAssertion.cs b/TUnit.Assertions/Conditions/NumericIsWithinPercentOfAssertion.cs
index 2457669be7..09f75cbe67 100644
--- a/TUnit.Assertions/Conditions/NumericIsWithinPercentOfAssertion.cs
+++ b/TUnit.Assertions/Conditions/NumericIsWithinPercentOfAssertion.cs
@@ -40,7 +40,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<double> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // Handle NaN comparisons
@@ -121,7 +121,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<float> me
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // Handle NaN comparisons
@@ -198,7 +198,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<int> meta
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var diff = Math.Abs((double)value - _expected);
@@ -251,7 +251,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<long> met
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var diff = Math.Abs((double)value - _expected);
@@ -304,7 +304,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<decimal>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var diff = Math.Abs(value - _expected);
diff --git a/TUnit.Assertions/Conditions/PredicateAssertions.cs b/TUnit.Assertions/Conditions/PredicateAssertions.cs
index b8e8603600..904b20a98f 100644
--- a/TUnit.Assertions/Conditions/PredicateAssertions.cs
+++ b/TUnit.Assertions/Conditions/PredicateAssertions.cs
@@ -30,7 +30,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (_predicate(value))
@@ -80,7 +80,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var comparer = GetComparer();
diff --git a/TUnit.Assertions/Conditions/ReadOnlyListAssertions.cs b/TUnit.Assertions/Conditions/ReadOnlyListAssertions.cs
index 9cade6088f..5d91d94373 100644
--- a/TUnit.Assertions/Conditions/ReadOnlyListAssertions.cs
+++ b/TUnit.Assertions/Conditions/ReadOnlyListAssertions.cs
@@ -31,7 +31,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -317,7 +317,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -378,7 +378,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -438,7 +438,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
     {
         if (metadata.Exception != null)
         {
-            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception);
         }
 
         if (metadata.Value == null)
@@ -465,7 +465,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
             }
             catch (Exception ex)
             {
-                return AssertionResult.Failed($"item at index {_index} did not satisfy assertion: {ex.Message}");
+                return AssertionResult.Failed($"item at index {_index} did not satisfy assertion: {ex.Message}", ex);
             }
         }
 
@@ -498,7 +498,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -555,7 +555,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TList> me
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -611,7 +611,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
     {
         if (metadata.Exception != null)
         {
-            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}");
+            return AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception);
         }
 
         if (metadata.Value == null)
@@ -637,7 +637,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TLi
             }
             catch (Exception ex)
             {
-                return AssertionResult.Failed($"last item did not satisfy assertion: {ex.Message}");
+                return AssertionResult.Failed($"last item did not satisfy assertion: {ex.Message}", ex);
             }
         }
 
diff --git a/TUnit.Assertions/Conditions/SetAssertions.cs b/TUnit.Assertions/Conditions/SetAssertions.cs
index cdb3f84f62..4763d96ff4 100644
--- a/TUnit.Assertions/Conditions/SetAssertions.cs
+++ b/TUnit.Assertions/Conditions/SetAssertions.cs
@@ -30,7 +30,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TSet> met
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -70,7 +70,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TSet> met
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -110,7 +110,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TSet> met
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -150,7 +150,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TSet> met
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -190,7 +190,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TSet> met
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -230,7 +230,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TSet> met
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
@@ -270,7 +270,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TSet> met
     {
         if (metadata.Exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {metadata.Exception.GetType().Name}", metadata.Exception));
         }
 
         if (metadata.Value == null)
diff --git a/TUnit.Assertions/Conditions/SpecializedEqualityAssertions.cs b/TUnit.Assertions/Conditions/SpecializedEqualityAssertions.cs
index 87ca9a9574..abdab1668c 100644
--- a/TUnit.Assertions/Conditions/SpecializedEqualityAssertions.cs
+++ b/TUnit.Assertions/Conditions/SpecializedEqualityAssertions.cs
@@ -423,7 +423,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TimeSpan>
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (_tolerance.HasValue)
diff --git a/TUnit.Assertions/Conditions/StringAssertions.cs b/TUnit.Assertions/Conditions/StringAssertions.cs
index 8879b37f08..ef0fdc653f 100644
--- a/TUnit.Assertions/Conditions/StringAssertions.cs
+++ b/TUnit.Assertions/Conditions/StringAssertions.cs
@@ -70,7 +70,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -189,7 +189,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -256,7 +256,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -323,7 +323,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -390,7 +390,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -457,7 +457,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -498,7 +498,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -610,7 +610,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<RegexMatc
             // Check what type of exception it is
             if (exception is InvalidOperationException)
             {
-                return Task.FromResult(AssertionResult.Failed(exception.Message));
+                return Task.FromResult(AssertionResult.Failed(exception.Message, exception));
             }
             // Rethrow native exceptions (ArgumentNullException, RegexParseException, RegexMatchTimeoutException)
             // so they can be tested with .Throws<T>()
@@ -682,7 +682,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<string> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         // Validate the regex pattern first (by creating a Regex object if we don't have one)
diff --git a/TUnit.Assertions/Conditions/StructuralEquivalencyAssertion.cs b/TUnit.Assertions/Conditions/StructuralEquivalencyAssertion.cs
index 29b80d4d89..92483280e1 100644
--- a/TUnit.Assertions/Conditions/StructuralEquivalencyAssertion.cs
+++ b/TUnit.Assertions/Conditions/StructuralEquivalencyAssertion.cs
@@ -75,7 +75,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}: {exception.Message}", exception));
         }
 
         var result = CompareObjects(
diff --git a/TUnit.Assertions/Conditions/ThrowsAssertion.cs b/TUnit.Assertions/Conditions/ThrowsAssertion.cs
index 3b4de430b7..809d5e0ec3 100644
--- a/TUnit.Assertions/Conditions/ThrowsAssertion.cs
+++ b/TUnit.Assertions/Conditions/ThrowsAssertion.cs
@@ -38,7 +38,7 @@ protected sealed override Task<AssertionResult> CheckAsync(EvaluationMetadata<TE
         // If there was an evaluation exception, something went wrong during evaluation
         if (evaluationException != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {evaluationException.GetType().Name}", evaluationException));
         }
 
         // The exception should be in the value field after MapException
diff --git a/TUnit.Assertions/Conditions/ToleranceBasedEqualsAssertion.cs b/TUnit.Assertions/Conditions/ToleranceBasedEqualsAssertion.cs
index ca9942a99d..3a4a9ad22e 100644
--- a/TUnit.Assertions/Conditions/ToleranceBasedEqualsAssertion.cs
+++ b/TUnit.Assertions/Conditions/ToleranceBasedEqualsAssertion.cs
@@ -70,7 +70,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         var actual = value!;
diff --git a/TUnit.Assertions/Conditions/TypeOfAssertion.cs b/TUnit.Assertions/Conditions/TypeOfAssertion.cs
index 7682f94b87..bc08a750e5 100644
--- a/TUnit.Assertions/Conditions/TypeOfAssertion.cs
+++ b/TUnit.Assertions/Conditions/TypeOfAssertion.cs
@@ -69,7 +69,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
@@ -309,7 +309,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<TValue> m
 
         if (exception != null)
         {
-            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}"));
+            return Task.FromResult(AssertionResult.Failed($"threw {exception.GetType().Name}", exception));
         }
 
         if (value == null)
diff --git a/TUnit.Assertions/Conditions/WaitsForAssertion.cs b/TUnit.Assertions/Conditions/WaitsForAssertion.cs
index 254019468a..e57df59e0f 100644
--- a/TUnit.Assertions/Conditions/WaitsForAssertion.cs
+++ b/TUnit.Assertions/Conditions/WaitsForAssertion.cs
@@ -86,8 +86,10 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<TVa
             ? $"Last error: {ExtractAssertionMessage(lastException)}"
             : "No attempts were made";
 
+        // Inner exception is the last AssertionException (not an originating cause) — kept whole
+        // because it carries the formatted assertion message useful for debugging.
         return AssertionResult.Failed(
-            $"assertion did not pass within {_timeout.TotalMilliseconds:F0}ms after {attemptCount} attempts. {lastErrorMessage}");
+            $"assertion did not pass within {_timeout.TotalMilliseconds:F0}ms after {attemptCount} attempts. {lastErrorMessage}", lastException);
     }
 
     /// <summary>
diff --git a/TUnit.Assertions/Conditions/WithInnerExceptionsAssertion.cs b/TUnit.Assertions/Conditions/WithInnerExceptionsAssertion.cs
index 302451d121..877684f36a 100644
--- a/TUnit.Assertions/Conditions/WithInnerExceptionsAssertion.cs
+++ b/TUnit.Assertions/Conditions/WithInnerExceptionsAssertion.cs
@@ -25,7 +25,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Agg
         var evaluationException = metadata.Exception;
         if (evaluationException != null)
         {
-            return AssertionResult.Failed($"threw {evaluationException.GetType().FullName}");
+            return AssertionResult.Failed($"threw {evaluationException.GetType().FullName}", evaluationException);
         }
 
         var aggregateException = metadata.Value;
@@ -46,7 +46,7 @@ protected override async Task<AssertionResult> CheckAsync(EvaluationMetadata<Agg
             }
             catch (Exception ex)
             {
-                return AssertionResult.Failed($"inner exceptions did not satisfy assertion: {ex.Message}");
+                return AssertionResult.Failed($"inner exceptions did not satisfy assertion: {ex.Message}", ex);
             }
         }
 
diff --git a/TUnit.Assertions/Core/Assertion.cs b/TUnit.Assertions/Core/Assertion.cs
index 5e047a409f..68f58ea0c6 100644
--- a/TUnit.Assertions/Core/Assertion.cs
+++ b/TUnit.Assertions/Core/Assertion.cs
@@ -242,7 +242,9 @@ protected Exception CreateException(AssertionResult result)
             at {Context.ExpressionBuilder}
             """;
 
-        return new AssertionException(message);
+        return result.Exception != null
+            ? new AssertionException(message, result.Exception)
+            : new AssertionException(message);
     }
 
     /// <summary>
diff --git a/TUnit.Assertions/Core/AssertionResult.cs b/TUnit.Assertions/Core/AssertionResult.cs
index e50b4d9424..0e528f1b0c 100644
--- a/TUnit.Assertions/Core/AssertionResult.cs
+++ b/TUnit.Assertions/Core/AssertionResult.cs
@@ -5,27 +5,35 @@ namespace TUnit.Assertions.Core;
 /// </summary>
 public readonly struct AssertionResult
 {
+    private static readonly AssertionResult _passed = new(true, string.Empty);
     internal static readonly Task<AssertionResult> _passedTask = Task.FromResult(Passed);
 
     public bool IsPassed { get; }
     public string Message { get; }
+    public Exception? Exception { get; }
 
-    private AssertionResult(bool isPassed, string message)
+    private AssertionResult(bool isPassed, string message, Exception? exception = null)
     {
         IsPassed = isPassed;
         Message = message ?? string.Empty;
+        Exception = exception;
     }
 
     /// <summary>
     /// Creates a passing assertion result.
     /// </summary>
-    public static AssertionResult Passed => new(true, string.Empty);
+    public static AssertionResult Passed => _passed;
 
     /// <summary>
     /// Creates a failing assertion result with a message describing what was found.
     /// </summary>
     public static AssertionResult Failed(string message) => new(false, message);
 
+    /// <summary>
+    /// Creates a failing assertion result with a message and an associated exception.
+    /// </summary>
+    public static AssertionResult Failed(string message, Exception? exception) => new(false, message, exception);
+
     /// <summary>
     /// Helper method to conditionally create a failed result.
     /// Returns Passed if condition is false, Failed with message if condition is true.
diff --git a/TUnit.Assertions/Core/AssertionResult{T}.cs b/TUnit.Assertions/Core/AssertionResult{T}.cs
index 46be85158f..a0626470cf 100644
--- a/TUnit.Assertions/Core/AssertionResult{T}.cs
+++ b/TUnit.Assertions/Core/AssertionResult{T}.cs
@@ -11,12 +11,14 @@ public readonly struct AssertionResult<T>
     public bool IsPassed { get; }
     public string Message { get; }
     public T? Value { get; }
+    public Exception? Exception { get; }
 
-    private AssertionResult(bool isPassed, string message, T? value)
+    private AssertionResult(bool isPassed, string message, T? value, Exception? exception = null)
     {
         IsPassed = isPassed;
         Message = message ?? string.Empty;
         Value = value;
+        Exception = exception;
     }
 
     /// <summary>
@@ -27,6 +29,8 @@ private AssertionResult(bool isPassed, string message, T? value)
 
     internal static AssertionResult<T> Failed(string message) => new(false, message, default);
 
+    internal static AssertionResult<T> Failed(string message, Exception? exception) => new(false, message, default, exception);
+
     /// <summary>
     /// Allows implicit conversion from a non-generic <see cref="AssertionResult"/> (failure only).
     /// Converting a passed <see cref="AssertionResult"/> without a value will throw.
@@ -39,6 +43,6 @@ public static implicit operator AssertionResult<T>(AssertionResult result)
                 "Cannot convert a passed AssertionResult to AssertionResult<T> without a value. Use AssertionResult<T>.Passed(value) instead.");
         }
 
-        return Failed(result.Message);
+        return new AssertionResult<T>(false, result.Message, default, result.Exception);
     }
 }
diff --git a/TUnit.Mocks.Assertions/WasCalledAssertion.cs b/TUnit.Mocks.Assertions/WasCalledAssertion.cs
index b49f499860..6c29ee631c 100644
--- a/TUnit.Mocks.Assertions/WasCalledAssertion.cs
+++ b/TUnit.Mocks.Assertions/WasCalledAssertion.cs
@@ -34,7 +34,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<ICallVeri
         }
         catch (MockVerificationException ex)
         {
-            return Task.FromResult(AssertionResult.Failed(ex.Message));
+            return Task.FromResult(AssertionResult.Failed(ex.Message, ex));
         }
     }
 
diff --git a/TUnit.Mocks.Assertions/WasNeverCalledAssertion.cs b/TUnit.Mocks.Assertions/WasNeverCalledAssertion.cs
index 455b49bbc1..76cd092e34 100644
--- a/TUnit.Mocks.Assertions/WasNeverCalledAssertion.cs
+++ b/TUnit.Mocks.Assertions/WasNeverCalledAssertion.cs
@@ -30,7 +30,7 @@ protected override Task<AssertionResult> CheckAsync(EvaluationMetadata<ICallVeri
         }
         catch (MockVerificationException ex)
         {
-            return Task.FromResult(AssertionResult.Failed(ex.Message));
+            return Task.FromResult(AssertionResult.Failed(ex.Message, ex));
         }
     }
 
diff --git a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet10_0.verified.txt b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet10_0.verified.txt
index d275bc4517..7599ea612d 100644
--- a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet10_0.verified.txt
+++ b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet10_0.verified.txt
@@ -2405,14 +2405,17 @@ namespace .Core
     }
     public readonly struct AssertionResult
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public static . Passed { get; }
         public static . FailIf(bool condition, string message) { }
         public static . Failed(string message) { }
+        public static . Failed(string message, ? exception) { }
     }
     public readonly struct AssertionResult<T>
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public T Value { get; }
diff --git a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt
index 8e96e7b507..0278b550de 100644
--- a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt
+++ b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet8_0.verified.txt
@@ -2384,14 +2384,17 @@ namespace .Core
     }
     public readonly struct AssertionResult
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public static . Passed { get; }
         public static . FailIf(bool condition, string message) { }
         public static . Failed(string message) { }
+        public static . Failed(string message, ? exception) { }
     }
     public readonly struct AssertionResult<T>
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public T Value { get; }
diff --git a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt
index 130da6da01..307bdde769 100644
--- a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt
+++ b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.DotNet9_0.verified.txt
@@ -2405,14 +2405,17 @@ namespace .Core
     }
     public readonly struct AssertionResult
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public static . Passed { get; }
         public static . FailIf(bool condition, string message) { }
         public static . Failed(string message) { }
+        public static . Failed(string message, ? exception) { }
     }
     public readonly struct AssertionResult<T>
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public T Value { get; }
diff --git a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.Net4_7.verified.txt b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.Net4_7.verified.txt
index d6535daa29..9d341ae661 100644
--- a/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.Net4_7.verified.txt
+++ b/TUnit.PublicAPI/Tests.Assertions_Library_Has_No_API_Changes.Net4_7.verified.txt
@@ -2156,14 +2156,17 @@ namespace .Core
     }
     public readonly struct AssertionResult
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public static . Passed { get; }
         public static . FailIf(bool condition, string message) { }
         public static . Failed(string message) { }
+        public static . Failed(string message, ? exception) { }
     }
     public readonly struct AssertionResult<T>
     {
+        public ? Exception { get; }
         public bool IsPassed { get; }
         public string Message { get; }
         public T Value { get; }
diff --git a/TUnit.TestProject/AssertionResultExceptionPropagationTests.cs b/TUnit.TestProject/AssertionResultExceptionPropagationTests.cs
new file mode 100644
index 0000000000..da9eaef75f
--- /dev/null
+++ b/TUnit.TestProject/AssertionResultExceptionPropagationTests.cs
@@ -0,0 +1,46 @@
+using TUnit.Assertions.Exceptions;
+
+namespace TUnit.TestProject;
+
+public class AssertionResultExceptionPropagationTests
+{
+    [Test]
+    public async Task Nested_Collection_Assertion_Failure_Preserves_InnerException()
+    {
+        var items = new[] { 1, 2, 3 };
+
+        AssertionException? caught = null;
+        try
+        {
+            await Assert.That(items).All().Satisfy(x => x.IsEqualTo(99));
+        }
+        catch (AssertionException ex)
+        {
+            caught = ex;
+        }
+
+        await Assert.That(caught).IsNotNull();
+        await Assert.That(caught!.InnerException).IsNotNull();
+        await Assert.That(caught.InnerException).IsTypeOf<AssertionException>();
+    }
+
+    [Test]
+    public async Task Mapped_Assertion_Failure_Preserves_InnerException()
+    {
+        var value = "hello";
+
+        AssertionException? caught = null;
+        try
+        {
+            await Assert.That(value).Satisfies(v => v.Length, length => length.IsEqualTo(99));
+        }
+        catch (AssertionException ex)
+        {
+            caught = ex;
+        }
+
+        await Assert.That(caught).IsNotNull();
+        await Assert.That(caught!.InnerException).IsNotNull();
+        await Assert.That(caught.InnerException).IsTypeOf<AssertionException>();
+    }
+}