diff --git a/src/functions/assert/String/Should-BeString.ps1 b/src/functions/assert/String/Should-BeString.ps1
index 1d05bbfbe..c6e2eaa73 100644
--- a/src/functions/assert/String/Should-BeString.ps1
+++ b/src/functions/assert/String/Should-BeString.ps1
@@ -3,7 +3,8 @@
         [String]$Expected,
         $Actual,
         [switch]$CaseSensitive,
-        [switch]$IgnoreWhitespace
+        [switch]$IgnoreWhitespace,
+        [switch]$TrimWhitespace
     )
 
     if ($Actual -isnot [string]) {
@@ -15,6 +16,11 @@
         $Actual = $Actual -replace '\s'
     }
 
+    if ($TrimWhitespace) {
+        $Expected = $Expected -replace '^\s+|\s+$'
+        $Actual = $Actual -replace '^\s+|\s+$'
+    }
+
     if (-not $CaseSensitive) {
         $Expected -eq $Actual
     }
@@ -43,6 +49,9 @@ function Should-BeString {
     .PARAMETER IgnoreWhitespace
     Indicates that the comparison should ignore whitespace.
 
+    .PARAMETER TrimWhitespace
+    Trims whitespace at the start and end of the string.
+
     .PARAMETER Because
     The reason why the actual value should be equal to the expected value.
 
@@ -77,13 +86,14 @@ function Should-BeString {
         [String]$Expected,
         [String]$Because,
         [switch]$CaseSensitive,
-        [switch]$IgnoreWhitespace
+        [switch]$IgnoreWhitespace,
+        [switch]$TrimWhitespace
     )
 
     $collectedInput = Collect-Input -ParameterInput $Actual -PipelineInput $local:Input -IsPipelineInput $MyInvocation.ExpectingInput -UnrollInput
     $Actual = $collectedInput.Actual
 
-    $stringsAreEqual = Test-StringEqual -Expected $Expected -Actual $Actual -CaseSensitive:$CaseSensitive -IgnoreWhitespace:$IgnoreWhiteSpace
+    $stringsAreEqual = Test-StringEqual -Expected $Expected -Actual $Actual -CaseSensitive:$CaseSensitive -IgnoreWhitespace:$IgnoreWhiteSpace -TrimWhitespace:$TrimWhitespace
     if (-not ($stringsAreEqual)) {
         $Message = Get-AssertionMessage -Expected $Expected -Actual $Actual -Because $Because -DefaultMessage "Expected <expectedType> <expected>, but got <actualType> <actual>."
         throw [Pester.Factory]::CreateShouldErrorRecord($Message, $MyInvocation.ScriptName, $MyInvocation.ScriptLineNumber, $MyInvocation.Line.TrimEnd([System.Environment]::NewLine), $true)
diff --git a/tst/functions/assert/String/Should-BeString.Tests.ps1 b/tst/functions/assert/String/Should-BeString.Tests.ps1
index f90ca04ce..db9e702fe 100644
--- a/tst/functions/assert/String/Should-BeString.Tests.ps1
+++ b/tst/functions/assert/String/Should-BeString.Tests.ps1
@@ -97,6 +97,19 @@ Describe "Should-BeString" {
         It "Can compare strings without whitespace" {
             Should-BeString -Expected " a b c " -Actual "abc" -IgnoreWhitespace
         }
+
+        It "Can compare strings without whitespace at the start or end" -ForEach @(
+            @{ Value = " abc" }
+            @{ Value = "abc " }
+            @{ Value = "abc`t" }
+            @{ Value = "`tabc" }
+        ) {
+            "  abc   " | Should-BeString -Expected "abc" -TrimWhitespace
+        }
+
+        It "Trimming whitespace does not remove it from inside of the string" {
+            { "a bc" | Should-BeString -Expected "abc" -TrimWhitespace } | Verify-AssertionFailed
+        }
     }
 
     It "Can be called with positional parameters" {