That’s not ideal.
In that respect, stable
will work better because the stable MAC address can be derived by hashing the SSID and other info (as specified with the stable-id
setting), so unless the ‘coffee shop’ and the ‘hotel’ use the same SSID, they will automatically be unable to be connected by the surveillance. However if you repeatedly visit the same ‘coffee shop’ then you will have the same MAC address every time you use that WAP, which is not ideal. The documentation gives you other options for the hashing, so maybe you can force it to behave better.
If setting stable-id
to ${RANDOM}
with cloned-mac-address
set to stable
gives better results than setting cloned-mac-address
to random
then that seems a bit unsatisfactory to me but hey this is Linux. It’s open source. If I don’t like it, I can change it. 
Obviously I would love to be able to test this out myself before advising you but …
Really, I would like to see it be the case that if you use the kill switch and you aren’t associated with a WAP then it should re-randomize the MAC address. In the mean time, you can probably manually run the MAC address randomization script when using the kill switch, or maybe you can hook the script into an interface up or down event.
Nah. If you control the DNS then you can induce me to establish a TCP connection to the wrong host but the (secure, SSL/TLS) connection will fail long before I get to enter a password because the wrong host is unable to use a valid certificate for example.com
OK, if you ignore the browser warnings about certificate failure then what you say applies.
BUT then the password won’t fail because any attacker worth his salt (security pun?) will do a correct Man In The Middle (MITM) attack and relay the session back to the real host - so the password will fail if and only if you did actually enter the wrong password.
If you entered the correct password then thereafter the attacker has your password and can monitor a lot of stuff just by logging in as you.
(Some sites tell you the last IP address used to login, which you could in some cases use to detect someone logging in as you, but that is highly likely not to be useful if you are using TOR, since the IP address will be all over the world.)