SSL handshake failed — TLS handshake failure through a proxy
The encrypted session could not be negotiated. Through a proxy this is usually one of two things: the proxy is not being asked to tunnel, or the target dislikes the fingerprint your client presents.
A proxy fixes part of this. If the handshake is rejected on fingerprint, the address is not what is being judged. A proxy helps only where the rejection is reputation-based and happens before the fingerprint is examined.
Why it happens
HTTPS sent to an HTTP proxy port without CONNECT.
The target requires a TLS version or cipher your client does not offer, or the reverse.
The target rejects handshakes whose fingerprint does not match a real browser — increasingly common.
A corporate MITM certificate not trusted by your client.
How to fix it
- Confirm the client is issuing CONNECT for HTTPS through an HTTP proxy.
- Try a client with a browser-shaped TLS fingerprint if the failure is target-specific.
- Never disable verification to make it work — that converts a diagnosable failure into a silent one.
FAQ
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