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Just for shits and giggles, I tried making a PKCS12 cert by going from pem and key. So that they were in the same file, neat thing is the errors went away, but still have TLS handshake failed

future reference to anyone that has this issue:

openssl req \
       -newkey rsa:2048  -keyout server.key \
       -x509 -days 365 -out server.crt

fill out the garbage it asked for and the des password

cat server.crt > server.pem
cat server.key >> server.pem

then edit the config.ini in witness_data_dir

rpc-tls-endpoint = 0.0.0.0:9000 # or whatever ip and port you want
server-pem = server.pem
server-pem-password = putstupidpasswordhere

when you run the cli_wallet use

cli_wallet -a server.pem -s wss://ipaddress:9000

you are welcome

still if this shit was document somewhere i wouldn't have fought with it all day, just sayin...

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