TCP socket upgrade never completes TLS handshake

I'm opening a TCP socket and then performing a TLS handshake. I am trying to await the opened promise, but it gets canceled in wrangler and hangs in production. Surprisingly enough, if I don't await the opened promise, then it works as expected, but only during wrangler dev! In production, if I omit awaiting on opened, then I get an error that the handshake failed as soon as I try to read from the secure socket. In this example I'm proxying through webshare to reach www.google.com. I've confirmed that it works over a basic curl. Any idea what I'm doing wrong? Thanks!
Cloudflare Docs
TCP sockets · Cloudflare Workers docs
Use the connect() API to create outbound TCP connections from Workers.
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