Powershell - Troubleshoot Networking Issues

I spent most of this week on dealing with these 2 exceptions:

• Exception calling "DownloadFile" with "2" argument(s): "An exception occurred during a WebClient request."
• Exception calling "DownloadFile" with "2" argument(s): "The underlying connection was closed: An unexpected error occured on a send."

The trigger was:

$Url = 'https://community.chocolatey.org/api/v2/package/chocholatey/1.1.0'
$file = Join-Path $pwd "chocoDownload.zip"
(New-Object System.Net.WebClient).DownloadFile($Url, $file)

That $Url was on the safe/accept list. So why does error occur?

TL;dr

Turns out that when hitting the url (on the allow/safe list), we get back a redirect pointing to another url that’s not on the allow/safe list.

The details

• What methods are used: Invoke-WebRequest or New-Object System.Net.WebClient?
• Try with curl
• Does the URL redirect somewhere? If so, where? Use the Get-UrlRedirect Function from https://github.com/juliusgb/utils/blob/main/powershell/CustomHelperUtils/UrlHelpers.ps1#L20-L33
• Does the DNS name have an IP address? (Use nslookup)
• Does the request reach the target ? (Use tracert)

• Does the request go through a Proxy? Show proxy settings

  • Show proxy settings: PS> Get-ItemProperty -Path "Registry::HKCU\Software\Microsoft\Windows\CurrentVersion\Internet Settings"
  • Another way WebProxy Settings: [System.Net.WebProxy]::GetDefaultProxy()