diff --git a/src/chocolatey.resources/helpers/functions/Get-ChocolateyWebFile.ps1 b/src/chocolatey.resources/helpers/functions/Get-ChocolateyWebFile.ps1
index 0b3fb35575..a5d6e7ec0e 100644
--- a/src/chocolatey.resources/helpers/functions/Get-ChocolateyWebFile.ps1
+++ b/src/chocolatey.resources/helpers/functions/Get-ChocolateyWebFile.ps1
@@ -301,7 +301,7 @@ Get-FtpFile
             $fileFullPath = $fileFullPath -replace '\\chocolatey\\chocolatey\\', '\chocolatey\'
             $fileDirectory = [System.IO.Path]::GetDirectoryName($fileFullPath)
             $originalFileName = [System.IO.Path]::GetFileName($fileFullPath)
-            $fileFullPath = Get-WebFileName -Url $url -DefaultName $originalFileName
+            $fileFullPath = Get-WebFileName -Url $url -DefaultName $originalFileName -Options $options
             $fileFullPath = Join-Path $fileDirectory $fileFullPath
             $fileFullPath = [System.IO.Path]::GetFullPath($fileFullPath)
         }
@@ -324,7 +324,7 @@ Get-FtpFile
     $headers = @{}
     if ($url.StartsWith('http')) {
         try {
-            $headers = Get-WebHeaders -Url $url -ErrorAction "Stop"
+            $headers = Get-WebHeaders -Url $url -ErrorAction "Stop" -Options $options
         }
         catch {
             if ($PSVersionTable.PSVersion -lt (New-Object 'Version' 3, 0)) {
@@ -333,7 +333,7 @@ Get-FtpFile
                 $originalProtocol = [System.Net.ServicePointManager]::SecurityProtocol
                 [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.SecurityProtocolType]::Ssl3
                 try {
-                    $headers = Get-WebHeaders -Url $url -ErrorAction "Stop"
+                    $headers = Get-WebHeaders -Url $url -ErrorAction "Stop" -Options $options
                 }
                 catch {
                     Write-Host "Attempt to get headers for $url failed.`n  $($_.Exception.Message)"
diff --git a/src/chocolatey.resources/helpers/functions/Get-WebFile.ps1 b/src/chocolatey.resources/helpers/functions/Get-WebFile.ps1
index 3a3f84f8fc..704d15d98d 100644
--- a/src/chocolatey.resources/helpers/functions/Get-WebFile.ps1
+++ b/src/chocolatey.resources/helpers/functions/Get-WebFile.ps1
@@ -199,7 +199,12 @@ Get-WebFileName
                     $req.UserAgent = $options.headers.$key
                 }
                 Default {
-                    $req.Headers.Add($key, $options.headers.$key)
+                    if ([System.Net.WebHeaderCollection]::IsRestricted($key)) {
+                        Write-Warning "Skipping restricted header `'$key`' not currently supported by Chocolatey"
+                    }
+                    else {
+                        $req.Headers.Add($key, $options.headers.$key)
+                    }
                 }
             }
         }
diff --git a/src/chocolatey.resources/helpers/functions/Get-WebHeaders.ps1 b/src/chocolatey.resources/helpers/functions/Get-WebHeaders.ps1
index 8fd96503bf..0e691ede62 100644
--- a/src/chocolatey.resources/helpers/functions/Get-WebHeaders.ps1
+++ b/src/chocolatey.resources/helpers/functions/Get-WebHeaders.ps1
@@ -52,6 +52,7 @@ Get-WebFile
     param(
         [parameter(Mandatory = $false, Position = 0)][string] $url = '',
         [parameter(Mandatory = $false, Position = 1)][string] $userAgent = 'chocolatey command line',
+        [parameter(Mandatory = $false, Position = 2)][hashtable] $options = @{Headers = @{} },
         [parameter(ValueFromRemainingArguments = $true)][Object[]] $ignoredArguments
     )
 
@@ -61,7 +62,7 @@ Get-WebFile
         return @{}
     }
 
-    $request = [System.Net.HttpWebRequest]::Create($url);
+    [System.Net.HttpWebRequest] $request = [System.Net.HttpWebRequest]::Create($url);
     $defaultCreds = [System.Net.CredentialCache]::DefaultCredentials
     if ($defaultCreds -ne $null) {
         $request.Credentials = $defaultCreds
@@ -128,7 +129,38 @@ Get-WebFile
 
     #http://stackoverflow.com/questions/518181/too-many-automatic-redirections-were-attempted-error-message-when-using-a-httpw
     $request.CookieContainer = New-Object System.Net.CookieContainer
-    if ($userAgent -ne $null) {
+
+    if ($options.Headers -ne $null) {
+        foreach ($key in $options.Headers.Keys) {
+            # https://learn.microsoft.com/en-us/dotnet/api/system.net.httpwebrequest.headers?view=net-8.0#remarks
+            switch ($key.ToLower()) {
+                'accept' { $request.Accept = $options.Headers[$key] }
+                'connection' { }
+                'content-length' { $request.ContentLength = $options.Headers[$key] }
+                'content-type' { $request.ContentType = $options.Headers[$key] }
+                'expect' { $request.Expect = $options.Headers[$key] }
+                'date' { $request.Date = $options.Headers[$key] }
+                'host' { $request.Host = $options.Headers[$key] }
+                'if-modified-since' { $request.IfModifiedSince = $options.Headers[$key] }
+                'range' { }
+                'referer' { $request.Referer = $options.Headers[$key] }
+                'transfer-encoding' { }
+                'user-agent' { $request.UserAgent = $options.Headers[$key] }
+
+                Default {
+                    if ([System.Net.WebHeaderCollection]::IsRestricted($key)) {
+                        Write-Warning "Skipping restricted header `'$key`' not currently supported by Chocolatey"
+                    }
+                    else {
+                        # Only add headers that don't match a request property
+                        $request.Headers.Add($key, $options.Headers[$key])
+                    }
+                }
+            }
+        }
+    }
+
+    if ($userAgent -ne $null -and $options.Headers['User-Agent'] -eq $null) {
         Write-Debug "Setting the UserAgent to `'$userAgent`'"
         $request.UserAgent = $userAgent
     }