Within Workstation I have Icedove installed, and there I have several different email accounts with different pseudononymous identities that I don’t want linked to each other by any external third party.
My question is: Is it a bad idea to have them all configured in the same Icedove app, within the same Workstation, all checking for email at the same time? I know that they will all use the same Tor circuit simultaneously, and all contact the various email servers at once from the same tor exit node, but as I understand it, anyone watching the exit node traffic cannot know that all these requests also came from the exact same circuit and originating source, since lots of people could be connected to the same end exit node from different places. An observing party can’t see the whole circuit path, just the exit node traffic to the destination server, correct?
However I suppose it might be bad enough that all of the three or four email identities are seen to always check for messages at the same time together, always from the same exit node as a group, and after enough noticing of this pattern, it could be reasoned that the requests are all coming from the same place/user.
Or, does the stream isolation feature work such that each email server connection is routed through a different circuit even if the connections are all initiated simultaneously?
I have read the documentation here: https://www.whonix.org/wiki/Stream_Isolation
And I think it suggests that Whonix handles Icedove in this more intelligent/secure way, even though it isn’t pre-installed. I installed it along with Enigmail, but I had to uninstall Torbirdy because it completely prevented me from ever creating a new email account from within Icedove, every time I tried. Hopefully this configuration is safe enough.