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A sneak peek at the dissector code seems to suggest that the file is (re-)read whenever a new connection establishment is seen in the capture. That would happen when a redirection takes place to feed the tap into the TCP stream window.

Situation where this does not work could be delayed writes to the key log file by the browser, missing TLS connection establishment in the capture, optimisation/shortcuts in the dissector preventing the key log file read to happen for taps. It would take some experimentation to get to the bottom of this. Therefore this would be an item to file an issue report on, so that someone with time/knowledge can work on it.

A sneak peek at the dissector code seems to suggest that the file is (re-)read whenever a new connection establishment is seen in the capture. That would happen when a redirection redissection takes place to feed the tap into the TCP stream window.

Situation where this does not work could be delayed writes to the key log file by the browser, missing TLS connection establishment in the capture, optimisation/shortcuts in the dissector preventing the key log file read to happen for taps. It would take some experimentation to get to the bottom of this. Therefore this would be an item to file an issue report on, so that someone with time/knowledge can work on it.