diff --git a/Functions/Assertions/Should.ps1 b/Functions/Assertions/Should.ps1
index 6667ee85e..c611e6018 100644
--- a/Functions/Assertions/Should.ps1
+++ b/Functions/Assertions/Should.ps1
@@ -59,14 +59,14 @@ function Get-FailureMessage($shouldArgs, $value) {
 
     return (& $failureMessageFunction $value $shouldArgs.ExpectedValue)
 }
-function New-ShouldException ($Message,$Line) {
+function New-ShouldException ($Message, $Line, $LineText) {
     $exception = New-Object Exception $Message
     $errorID = 'PesterAssertionFailed'
     $errorCategory = [Management.Automation.ErrorCategory]::InvalidResult
-    $errorRecord = New-Object Management.Automation.ErrorRecord $exception, $errorID, $errorCategory, $null
-    $errorRecord.ErrorDetails = "$Message failed at line: $line"
-
-    $errorRecord
+    # we use ErrorRecord.TargetObject to pass structured information about the error to a reporting system.
+    $targetObject = @{message = $Message; line = $line; linetext = $LineText}
+    $errorRecord = New-Object Management.Automation.ErrorRecord $exception, $errorID, $errorCategory, $targetObject
+    return $errorRecord
 }
 
 function Should {
@@ -83,11 +83,13 @@ function Should {
             $testFailed = Get-TestResult $parsedArgs $value
 
             if ($testFailed) {
+                $ShouldExceptionLineText = $MyInvocation.Line.TrimEnd("`n")
                 $ShouldExceptionLine = $MyInvocation.ScriptLineNumber
+
                 $failureMessage = Get-FailureMessage $parsedArgs $value
 
 
-                throw ( New-ShouldException -Message $failureMessage -Line $ShouldExceptionLine )
+                throw ( New-ShouldException -Message $failureMessage -Line $ShouldExceptionLine -LineText $ShouldExceptionLineText)
             }
         } until ($input.MoveNext() -eq $false)
     }
diff --git a/Functions/It.ps1 b/Functions/It.ps1
index fe0922c3a..0ee571067 100644
--- a/Functions/It.ps1
+++ b/Functions/It.ps1
@@ -274,18 +274,23 @@ function Get-PesterResult {
 
     if ($exception.FullyQualifiedErrorID -eq 'PesterAssertionFailed')
     {
-        $failureMessage = $exception.exception.message
+        # we use TargetObject to pass structured information about the error.
+        $details = $exception.TargetObject
+        
+        $failureMessage = $details.message
         $file = $test.File
-        $line = if ( $exception.ErrorDetails.message -match "\d+$" )  { $matches[0] }
+        $line = $details.line
+        $lineText = "`n$line`: $($details.linetext)"
     }
     else {
         $failureMessage = $exception.ToString()
         $file = $Exception.InvocationInfo.ScriptName
         $line = $Exception.InvocationInfo.ScriptLineNumber
+        $lineText = ''
     }
 
     $testResult.failureMessage = $failureMessage -replace "Exception calling", "Assert failed on"
-    $testResult.stackTrace = "at line: $line in $file"
+    $testResult.stackTrace = "at line: $line in ${file}${lineText}"
 
     return $testResult
 }