diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
index 567a98ebfb9..9860d8c2179 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
@@ -1488,14 +1488,16 @@ internal void SetRequestContent(HttpRequestMessage request, string content)
             ArgumentNullException.ThrowIfNull(content);
             
             Encoding encoding = null;
-            if (ContentType is not null)
+            string contentType = WebSession.ContentHeaders[HttpKnownHeaderNames.ContentType];
+
+            if (contentType is not null)
             {
                 // If Content-Type contains the encoding format (as CharSet), use this encoding format
                 // to encode the Body of the WebRequest sent to the server. Default Encoding format
                 // would be used if Charset is not supplied in the Content-Type property.
                 try
                 {
-                    MediaTypeHeaderValue mediaTypeHeaderValue = MediaTypeHeaderValue.Parse(ContentType);
+                    MediaTypeHeaderValue mediaTypeHeaderValue = MediaTypeHeaderValue.Parse(contentType);
                     if (!string.IsNullOrEmpty(mediaTypeHeaderValue.CharSet))
                     {
                         encoding = Encoding.GetEncoding(mediaTypeHeaderValue.CharSet);
@@ -1506,7 +1508,7 @@ internal void SetRequestContent(HttpRequestMessage request, string content)
                     if (!SkipHeaderValidation)
                     {
                         ValidationMetadataException outerEx = new(WebCmdletStrings.ContentTypeException, ex);
-                        ErrorRecord er = new(outerEx, "WebCmdletContentTypeException", ErrorCategory.InvalidArgument, ContentType);
+                        ErrorRecord er = new(outerEx, "WebCmdletContentTypeException", ErrorCategory.InvalidArgument, contentType);
                         ThrowTerminatingError(er);
                     }
                 }
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 2da345fcd3a..01946e5c5f0 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -568,6 +568,13 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
         $Result.Output.Content | Should -Match '⡌⠁⠧⠑ ⠼⠁⠒  ⡍⠜⠇⠑⠹⠰⠎ ⡣⠕⠌'
     }
 
+    It "Invoke-WebRequest -ContentType overwrites Content-Type from -Headers." {
+        $uri = Get-WebListenerUrl -Test 'POST'
+        $command = "Invoke-WebRequest -Uri '$uri' -ContentType 'application/json' -Headers @{'Content-Type'='plain/text'} -Method 'POST'"
+        $result = ExecuteWebCommand -command $command
+        $result.Output.BaseResponse.RequestMessage.Content.Headers.ContentType.MediaType | Should -BeExactly 'application/json'
+    }
+
     It "Invoke-WebRequest supports sending request as UTF-8." {
         $uri = Get-WebListenerUrl -Test 'POST'
         # Body must contain non-ASCII characters
@@ -576,7 +583,7 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
         $result = ExecuteWebCommand -command $command
         ValidateResponse -response $result
 
-        $Result.Output.Encoding.BodyName | Should -BeExactly 'utf-8'
+        $result.Output.Encoding.BodyName | Should -BeExactly 'utf-8'
         $object = $Result.Output.Content | ConvertFrom-Json
         $object.Data | Should -BeExactly 'проверка'
     }
@@ -2338,6 +2345,13 @@ Describe "Invoke-RestMethod tests" -Tags "Feature", "RequireAdminOnWindows" {
         $Result.Output | Should -Match '⡌⠁⠧⠑ ⠼⠁⠒  ⡍⠜⠇⠑⠹⠰⠎ ⡣⠕⠌'
     }
 
+    It "Invoke-RestMethod -ContentType overwrites Content-Type from -Headers." {
+        $uri = Get-WebListenerUrl -Test 'POST'
+        $command = "Invoke-RestMethod -Uri '$uri' -ContentType 'application/json' -Headers @{'Content-Type'='plain/text'} -Method 'POST'"
+        $result = ExecuteWebCommand -command $command
+        $result.Output.headers."Content-Type" | Should -BeExactly 'application/json'
+    }
+
     It "Invoke-RestMethod supports sending requests as UTF8" {
         $uri = Get-WebListenerUrl -Test POST
         # Body must contain non-ASCII characters