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S/MIME signing SMTP proxy server

This SMTP server listens on port 1025, signs all incoming messages (to which it has S/MIME key-certificate pairs), and forwards them to an upstream SMTP server.

At the moment, only a single upstream server is supported, which is currently hardcoded to be gmail MX server, so as of writing it's useful only for messages sent to a @gmail.com address. That's fine for me, but PRs fixing this are welcome!

Installation

Assuming you're using Actalis free S/MIME certificates for [email protected] email, they send you a file called [email protected] and show a password for it. You need to decrypt and split it into 4 parts.

  • First, run this command:

      openssl pkcs12 -in PKCS12_Credential_*.pfx -info -nodes

    After providing your password, you will see an output like this (long sequences of base64 gibberish shortened):

      MAC: sha1, Iteration 102400
  MAC length: 20, salt length: 20
  PKCS7 Data
  Shrouded Keybag: pbeWithSHA1And3-KeyTripleDES-CBC, Iteration 51200
  Bag Attributes
      localKeyID: 6E 14 EB CD E8 72 EF 19 6F 68 D5 59 B9 77 FD E1 FE 2D 8A C9 
      friendlyName: [email protected]
  Key Attributes: <No Attributes>
  -----BEGIN PRIVATE KEY-----
  bEHeNq68nxa/K2TAq2SoMDurGDeJYBNAYiFL8DJ2i4J7uXR7gL7Ac1Ao+y48/IXV
  ...
  G7sztqA9XDQv6W+2roVlkQ==
  -----END PRIVATE KEY-----
  PKCS7 Encrypted data: pbeWithSHA1And40BitRC2-CBC, Iteration 51200
  Certificate bag
  Bag Attributes
      localKeyID: 6E 14 EB CD E8 72 EF 19 6F 68 D5 59 B9 77 FD E1 FE 2D 8A C9 
      friendlyName: [email protected]
  subject=CN = [email protected]

  issuer=C = IT, ST = Bergamo, L = Ponte San Pietro, O = Actalis S.p.A., CN = Actalis Client Authentication CA G3

  -----BEGIN CERTIFICATE-----
  clIWZ6PJ6L44k8UH+PckivhAOVmIgtxhpltr4CGrb29Z5y7h5dK1wV8PZWpgqcNs
  ...
  LaayQOjHRhXJ8Q//g/sqdw==
  -----END CERTIFICATE-----
  Certificate bag
  Bag Attributes
      friendlyName: Actalis Client Authentication CA G3
  subject=C = IT, ST = Bergamo, L = Ponte San Pietro, O = Actalis S.p.A., CN = Actalis Client Authentication CA G3

  issuer=C = IT, L = Milan, O = Actalis S.p.A./03358520967, CN = Actalis Authentication Root CA

  -----BEGIN CERTIFICATE-----
  MIIHbTCCBVWgAwIBAgIQFxA+3j2KHLXKBlGT58pDazANBgkqhkiG9w0BAQsFADBr
  ...
  nMQBstsymBBgdEKO+tTHHCMnJQVvZn7jRQ20wXgxMrvN
  -----END CERTIFICATE-----
  Certificate bag
  Bag Attributes
      friendlyName: Actalis Authentication Root CA
  subject=C = IT, L = Milan, O = Actalis S.p.A./03358520967, CN = Actalis Authentication Root CA

  issuer=C = IT, L = Milan, O = Actalis S.p.A./03358520967, CN = Actalis Authentication Root CA

  -----BEGIN CERTIFICATE-----
  MIIFuzCCA6OgAwIBAgIIVwoRl0LE48wwDQYJKoZIhvcNAQELBQAwazELMAkGA1UE
  ...
  LnPqZih4zR0Uv6CPLy64Lo7yFIrM6bV8+2ydDKXhlg==
  -----END CERTIFICATE-----

  • The first gibberish base64-encoded data between and including -----BEGIN PRIVATE KEY----- and -----END PRIVATE KEY----- is your key. Save it to data/keys/[email protected] file (replace [email protected] with your actual email address):

      cat >data/keys/[email protected]
  -----BEGIN PRIVATE KEY-----
  bEHeNq68nxa/K2TAq2SoMDurGDeJYBNAYiFL8DJ2i4J7uXR7gL7Ac1Ao+y48/IXV
  ...
  G7sztqA9XDQv6W+2roVlkQ==
  -----END PRIVATE KEY-----
  ^D

  • Then, three certificates follow. You can distinguish them by "subject" and "issuer" lines above -----BEGIN CERTIFICATE----- ... -----END CERTIFICATE----- blocks of base64.

    First one is the certificate specific for your email address and goes to appropriately-named file:

      cat >data/certs/[email protected]
  -----BEGIN CERTIFICATE-----
  clIWZ6PJ6L44k8UH+PckivhAOVmIgtxhpltr4CGrb29Z5y7h5dK1wV8PZWpgqcNs
  ...
  LaayQOjHRhXJ8Q//g/sqdw==
  -----END CERTIFICATE-----
  ^D

  • Second one is so-called intermediate certificate, which stands between root certificate which everyone trusts, and your specific cert:

      cat >data/certs/intermediate.crt
  -----BEGIN CERTIFICATE-----
  MIIHbTCCBVWgAwIBAgIQFxA+3j2KHLXKBlGT58pDazANBgkqhkiG9w0BAQsFADBr
  ...
  nMQBstsymBBgdEKO+tTHHCMnJQVvZn7jRQ20wXgxMrvN
  -----END CERTIFICATE-----
  ^D

    Note that at this moment, this script supports only a single intermediate certificate. That's fine for me, but if you need more - feel free to improve it!

  • Third certificate is the root one, which is self-signed (you can see that "issuer" and "subject" lines are the same for it), and theoretically everyone should already have it. But we still include it:

      cat >data/certs/root.crt
  -----BEGIN CERTIFICATE-----
  MIIFuzCCA6OgAwIBAgIIVwoRl0LE48wwDQYJKoZIhvcNAQELBQAwazELMAkGA1UE
  ...
  LnPqZih4zR0Uv6CPLy64Lo7yFIrM6bV8+2ydDKXhlg==
  -----END CERTIFICATE-----
  ^D

Usage

Just connect to port 1025 and talk SMTP :)

Alternatevly, if you wish to enable S/MIME for selected recepients (as of now, gmail only, see note above), you can use transport_maps feature in postfix:

$ grep transport_maps /postfix/conf/main.cf
transport_maps = texthash:/postfix/conf/transport_maps.txt
$ cat /postfix/conf/transport_maps.txt
[email protected] smtp:[padlock]:1025

Security note

Note that since signing key is stored on the server, this does not add any extra security compared to DKIM signature.

The only purpose of this server is to satisfy those email clients/servers/users who can't/don't check/show DKIM signatures, but have an option to check/show S/MIME ones.