PowerShell

Upgrade a Plain TCP Connection to TLS

Demonstrates Socket.ConvertToSsl, which upgrades an already-connected plain TCP socket to TLS by performing a client-side TLS handshake over the existing connection.

Background. This supports STARTTLS-style upgrades, where a protocol begins in plaintext and switches to TLS at a defined point. Perform the protocol-specific negotiation first, then call ConvertToSsl.

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Add-Type -Path "C:\chilkat\ChilkatDotNet47-x64\ChilkatDotNet47.dll"

$success = $false

$socket = New-Object Chilkat.Socket

#  Connect as plain TCP (no TLS yet).
$bTls = $false
$maxWaitMs = 5000
$success = $socket.Connect("example.com",5000,$bTls,$maxWaitMs)
if ($success -eq $false) {
    $($socket.LastErrorText)
    exit
}

#  At the point where the application protocol permits a STARTTLS-style upgrade, perform any required
#  negotiation, then upgrade the existing connection to TLS with a client-side handshake.
$success = $socket.ConvertToSsl()
if ($success -eq $false) {
    $($socket.LastErrorText)
    exit
}

$("Connection upgraded to TLS.")