Developer spends over an hour sending one Gmail from China after six failed attempts

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A developer in Guangzhou, China, recently spent over an hour trying to send a single email using Gmail, despite the task taking only 15 minutes to draft. China's Great Firewall blocks Gmail's SMTP ports through deep packet inspection, resetting connections whenever it detects smtp.gmail.com in plaintext SNI headers. The developer tried six programmatic approaches — including Python smtplib, proxied curl, PySocks, raw socket tunneling, and Node.js with Nodemailer — each failing due to a mix of GFW restrictions, Windows TLS bugs, and proxy routing issues. Every attempt to route SMTP traffic through a local Clash proxy also fell short, either due to schannel incompatibilities or incorrect proxy rule configurations sending traffic directly into the firewall. Ultimately, the developer abandoned all programmatic methods and simply used Gmail's web interface in Chrome to send the email successfully.

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