Debug TLS Handshakes using .NET

Trace-TlsHandshake.ps1

# Copyright: (c) 2022, Jordan Borean (@jborean93) <[email protected]>
# MIT License (see LICENSE or https://opensource.org/licenses/MIT)

Function Trace-TlsHandshake {
    <#
    .SYNOPSIS
    TLS Handshake Diagnostics.

    .DESCRIPTION
    Performs a TLS handshake and returns diagnostic information about that
    exchange. It can also be used to capture the raw TLS packets used in the
    exchange through the -CapturePacket switch.

    .PARAMETER HostName
    The hostname to connect to.

    .PARAMETER Port
    The port to connect to, defaults to 443 which is commonly used for https.

    .PARAMETER Protocol
    The TLS protocol to restrict the handshake to. The default will use the
    OS defaults but this can be used to use a specific protocol.

    .PARAMETER CipherSuite
    Override the cipher suite selection policy. The default will use the OS
    defaults. Currently only Linux and macOS can define an explicit cipher
    suite policy. The dotnet API does not support this for Windows
    https://github.com/dotnet/runtime/issues/23818.

    .PARAMETER CapturePacket
    Capture the raw TLS packets and store them in the output Packets property.
    This is experimental but can be used to analyze data not available through
    PowerShell/.NET.

    .EXAMPLE
    Trace-TlsHandshake -HostName google.com

    .OUTPUTS
    This cmdlet outputs an object with the following properties:

        Protocol
        The TLS protocol that was negotiated. The values correspond to the
        SslProtocols enum
        https://docs.microsoft.com/en-us/dotnet/api/system.security.authentication.sslprotocols?view=net-6.0

        Cipher
        The cipher suite which was negotiated. The values correspond to the
        TlsCipherSuite enum
        https://docs.microsoft.com/en-us/dotnet/api/system.net.security.tlsciphersuite?view=net-6.0

        KeyStrength
        The strength of the key exchange algorithm that was negotiated.

        Certificate
        The certificate of the target host.

        Chain
        A chain of certificate authorities associated with the remote
        certificate.

        VerificationStatus
        The cert verifcation result. The values can be set to the following:

            None - No errors, verification succeeded
            RemoteCertificateChainErrors - Errors in the chain
            RemoteCertificateNameMismatch - Certificate name mismatched
            RemoteCertificateNotAvailable - No certificate was available

            The enums are based off
            https://docs.microsoft.com/en-us/dotnet/api/system.net.security.sslpolicyerrors?view=net-6.0


        Packets:
        The raw TLS packets that were exchanged from the client and host. This
        will be empty if -CapturePacket was not set.


    The object in the Packets list contain the following properties:

        Direction:
        The direction of the packet; Outgoing for packets sent from the client
        and Incoming for packets sent from the server.

        ContentType:
        The raw content type of the TLS record.

        Version:
        The raw version id of the TLS record.

        Length:
        The length of the TLS record payload

        Data:
        The full TLS record packet, this contains both the TLS record header
        (first 5 bytes) as well as the remaining payload (size of Length).

    .NOTES
    This cmdlet is designed to replicate some of the same functionality that
    exists in the openssl s_client -connect command.

    This must run with PowerShell 7+.
    #>
    [CmdletBinding()]
    param (
        [Parameter(Mandatory)]
        [string]
        $HostName,

        [Parameter()]
        [int]
        $Port = 443,

        [Parameter()]
        [System.Security.Authentication.SslProtocols]
        $Protocol = [System.Security.Authentication.SslProtocols]::None,

        [Parameter()]
        [System.Net.Security.CipherSuitesPolicy]
        $CipherSuite = $null,

        [Parameter()]
        [switch]
        $CapturePacket
    )

    $bufferSize = 16KB
    $pipeName = "tls-test-$([Guid]::NewGuid())"
    try {
        Write-Verbose -Message "Connecting to $($HostName):$Port"
        $socket = [System.Net.Sockets.TcpClient]::new($HostName, $Port)
        $socketStream = $socket.GetStream()

        Write-Verbose -Message "Creating named pipe for packet capture called '$pipeName'"
        $serverPipe = [System.IO.Pipes.NamedPipeServerStream]::new(
            $pipeName,
            [System.IO.Pipes.PipeDirection]::InOut,
            1,
            [System.IO.Pipes.PipeTransmissionMode]::Byte,
            [System.IO.Pipes.PipeOptions]"Asynchronous, CurrentUserOnly",
            $bufferSize,
            $bufferSize
        )
        $clientPipe = [System.IO.Pipes.NamedPipeClientStream]::new(
            ".",
            $pipeName,
            [System.IO.Pipes.PipeDirection]::InOut,
            [System.IO.Pipes.PipeOptions]"Asynchronous, CurrentUserOnly"
        )

        Write-Verbose -Message "Connecting client and server named pipes"
        $waitTask = $serverPipe.WaitForConnectionAsync()
        $clientPipe.Connect()
        while (-not $waitTask.AsyncWaitHandle.WaitOne(200)) { }
        $null = $waitTask.GetAwaiter().GetResult()

        $tlsPipeRecorder = {
            [CmdletBinding()]
            param (
                [Parameter(Mandatory)]
                [string]
                $Id,

                [Parameter(Mandatory)]
                [System.IO.Stream]
                $Incoming,

                [Parameter(Mandatory)]
                [System.IO.Stream]
                $Outgoing,

                [Parameter(Mandatory)]
                [AllowEmptyCollection()]
                [System.Collections.Generic.List[PSObject]]
                $MessageList,

                [Parameter(Mandatory)]
                [System.Threading.CancellationToken]
                $CancelToken
            )

            try {
                $buffer = [byte[]]::new(16KB)
                while ($true) {
                    $task = $Incoming.ReadAsync($buffer, 0, 5, $CancelToken)
                    while (-not $task.AsyncWaitHandle.WaitOne(200)) { }
                    $null = $task.GetAwaiter().GetResult()

                    # The length of the TLS Record is a big endian UInt16 value
                    $msgLength = (([uint16]$buffer[3]) -shl 8) -bor $buffer[4]
                    $null = $Incoming.Read($buffer, 5, $msgLength)
                    $Outgoing.Write($buffer, 0, $msgLength + 5)
                    $Outgoing.Flush()

                    $msgObj = [PSCustomObject]@{
                        PSTypeName  = 'Tls.Record'
                        Direction   = $Id
                        ContentType = $buffer[0]
                        Version     = (([uint16]$buffer[1]) -shl 8) -bor $buffer[2]
                        Length      = $msgLength
                        Data        = [byte[]]($buffer[0..($msgLength + 4)])
                    }
                    $MessageList.Add($msgObj)
                }
            }
            catch [System.OperationCanceledException] {}
            catch {
                [Console]::WriteLine("$Id Failed - $_")
                throw
            }
        }

        $cancelToken = [System.Threading.CancellationTokenSource]::new()
        $msgList = [System.Collections.Generic.List[PSObject]]::new()
        $backgroundTasks = @(if ($CapturePacket) {
                $psRead = [PowerShell]::Create()
                $psRead.AddScript($tlsPipeRecorder).AddParameters(@{
                        Id          = "Outgoing"
                        Incoming    = $clientPipe
                        Outgoing    = $socketStream
                        MessageList = $msgList
                        CancelToken = $cancelToken.Token
                    }).InvokeAsync()
                $psWrite = [PowerShell]::Create()
                $psWrite.AddScript($tlsPipeRecorder).AddParameters(@{
                        Id          = "Incoming"
                        Incoming    = $socketStream
                        Outgoing    = $clientPipe
                        MessageList = $msgList
                        CancelToken = $cancelToken.Token
                    }).InvokeAsync()
            })

        $sslOptions = @{
            EnabledSslProtocols = $Protocol
            TargetHost          = $HostName
        }
        if ($CipherSuite) {
            $sslOptions.CipherSuitesPolicy = $CipherSuite
        }

        $certCallback = {
            [CmdletBinding()]
            param (
                [object]$SenderObj,
                [System.Security.Cryptography.X509Certificates.X509Certificate]$Certificate,
                [System.Security.Cryptography.X509Certificates.X509Chain]$Chain,
                [System.Net.Security.SslPolicyErrors]$PolicyErrors
            )

            $SenderObj._CertCallbackBag.Certificate = $Certificate
            $SenderObj._CertCallbackBag.Chain = $Chain
            $SenderObj._CertCallbackBag.PolicyErrors = $PolicyErrors
            $true
        }
        $targetStream = $CapturePacket ? $serverPipe : $socketStream
        $tlsStream = [System.Net.Security.SslStream]::new($targetStream, $true, $certCallback)

        # This is used in the callback to smuggle back the callback params
        $callbackInfo = @{}
        $tlsStream.PSObject.Properties.Add(
            [System.Management.Automation.PSNoteProperty]::new('_CertCallbackBag', $callbackInfo))

        Write-Verbose "Starting TLS Handshake"
        try {
            $tlsStream.AuthenticateAsClient($sslOptions)
            Write-Verbose "TLS Handshake complete"
        }
        catch {
            # The exception here may contain an unhelpful see inner exception,
            # raise the inner exception to display a more helpful error.
            $exp = $_.Exception.InnerException
            if ($exp.Message -like "*see inner exception*") {
                $exp = $exp.InnerException
            }

            $err = [System.Management.Automation.ErrorRecord]::new(
                $exp,
                "TLSHandsakeFailure",
                [System.Management.Automation.ErrorCategory]::ProtocolError,
                $HostName)
            $err.ErrorDetails = "TLS Handshake Failure: $($exp.Message)"
            $PSCmdlet.WriteError($err)
        }
        finally {
            $cancelToken.Cancel()
            foreach ($task in $backgroundTasks) {
                while (-not $task.AsyncWaitHandle.WaitOne(200)) { }
                $task.GetAwaiter().GetResult()
            }
        }

        [PSCustomObject]@{
            PSTypeName         = 'Tls.Handshake'
            Protocol           = $tlsStream.SslProtocol
            Cipher             = $tlsStream.NegotiatedCipherSuite
            KeyStrength        = $tlsStream.KeyExchangeStrength
            Certificate        = $callbackInfo.Certificate
            Chain              = $callbackInfo.Chain
            VerificationStatus = $callbackInfo.PolicyErrors
            Packets            = $msgList
        }
    }
    finally {
        ${socketStream}?.Dispose()
        ${socket}?.Dispose()
        ${tlsStream}?.Dispose()
        ${clientPipe}?.Dispose()
        ${serverPipe}?.Dispose()
    }
}

I've had a further look and it seems like this is just not implemented on Windows with dotnet dotnet/runtime#23818.

Note: OpenSsl 1.1.1 or OSX is required. Windows is not supported at the moment.

I haven't seen any action for bringing support for this to Windows and even knowing the SSPI APIs to do so sounds a bit complex.

I'll just have to update the docstring to reflection this information.

What would be involved to make this work with a proxy? (basic auth authenticated ideally)

Guess have to do the CONNECT request etc.