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Self answered:
Root Cause: IPv6 Routing Configuration (/128 vs /64 prefix)

The TLS handshake failure was actually a network routing issue, not a certificate problem. Our netplan configuration used a /128 prefix:

A /128 prefix creates a single-host route with no subnet capability. When clients sent Initial packets, the kernel couldn't route responses back because destinations were considered outside the directly-connected network.

Solution: Changed to /64 prefix:

After this fix, IPv6 handshake completed successfully. The error code 0x6e (TLS_HANDSHAKE_FAILURE) was misleading—it occurred because the connection failed at the network layer before TLS could properly negotiate.

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Answer selected by toms-visuality
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