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A lot of the people I exchange emails with use services such as Google Mail. Recently it occurred to me that Google must maintain a social graph based on who exchanges emails with whom. It bogs me that a Google employee can potentially point to a number of email addresses and say: "These are the individuals X is in touch with."

How about the following approach to rendering the latter a tad more difficult:

  1. When I mail someone for the first time, a generic-sounding address (e.g. [email protected] or [email protected]) is generated.
  2. The new address is associated with the receiver.
  3. The email is sent with the newly generated address being used as the sender.
  4. Whenever that specific receiver wants to mail me, they will use the address generated in the first step.

Now for the questions:

  • Does anyone use such a scheme?
  • Do you think it's any good at all?
  • Are there existing solutions?
  • What Linux mail client might prove suitable for adding this functionality?
  • How to automate the generation of new addresses? Is there a provider offering an API that is sufficiently capable?
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  • What you're after is an outbound SMTP proxy that will re-address messages instead of simply forwarding them. What you want to avoid is for this SMTP proxy to include all the forwarded for headers and replace the original sender's address with a record stored in the SMTP proxy for the particular outbound message. e-MailRelay is one of them that could do that for you, but of course there are many other solutions like that. Google for 'SMTP proxy' or 'SMTP relaying proxy' and pick one that'll work on your OS.
    – TildalWave
    Commented Mar 10, 2013 at 15:34
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    Can see no practical benefit in this scheme. Are you being harassed by Google employees? It is a general rule that eavesdroppers keep low profile; if you are afraid of governments, this setup would not be of much hindrance to them. Using the Internet is akin to living within glass walls, and there is precious little you can do about it. Somebody, somewhere does keep a file on you... Commented Mar 10, 2013 at 16:25
  • How about going back to paper, envelopes and postal stamps? Commented Mar 11, 2013 at 11:23
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    The scenario involving Google served as an example. I'm not being harassed by Google employees, but I live in a repressive state and a lot of the people I exchange emails with are activists. I thought it worthwhile to reduce my "data footprint", especially as it involves only a setup effort, and then it'll work in the background for years. Commented Mar 12, 2013 at 14:56

2 Answers 2

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Does anyone use such a scheme?

Yes. I know several people who run their a mail server on their own domain. Every new contacts is treated as a potential spammer and everybody gets an unique email address.

Do you think it's any good at all?

That depends on your goals.

It suffices for your "2) address is associated with the receiver."
It is not enough to prevent your ISP or mail provider to track you.

Are there existing solutions?

The closest thing I can come up with are sites such as http://www.mailinator.com/ and http://spamgourmet.com/ . Those are used by lots of people, which means that you can not be tracked down just by looking at the domain. However you still have to trust the mail provider not to leak information.

What Linux mail client might prove suitable for adding this functionality?

No idea.

How to automate the generation of new addresses? Is there a provider offering an API that is sufficiently capable?

That depends on the previous answer.

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In addition to Hennes great answer (which implies my approach, but) I want to elaborate on the solution I use:

  • I have a personal domain and running my own mail server (well, the hosting package I pay for offers and maintains it).
  • I have created a catch-all mailbox, so every mail directed toward my domain will land in my inbox
  • Of course a generic spam filter is applied beforehand
  • I simply hand out each contact I want to single out, it's custom email like '[email protected]'
  • To stop individual spammers, I just put them on the spam list

Now, with this, I do not have to create actual inboxes and I can decide which contacts (if any) I want to pool into the same "virtual inbox".

I have used this for years now and it serves me well.

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