-----BEGIN PGP SIGNED MESSAGE----- In <199710131652.RAA02526@server.test.net>, on 10/13/97 at 05, Adam Back <aba@dcs.ex.ac.uk> said:

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I also personally prefer people to send me keys in email, because the pay per second phone lines here at home mean that I tend want to avoid doing too many online key lookups, so I think this would be an individually useful feature.

I do my keylookups automatically durning the msg filtering process which is done in parallel to the message Dl's.

A clever optimisation to be sure.

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The outbound message lookups are a little more time consuming but is compensated by fewer keys to look for both because fewer messages on the outbound side and the use of key caches on the client machine for the most used keys for sig verification and encryption.

I don't have a key cache, and my keyring is only 216k. But I'm curious about your automated process .. are you also checking all signatures that you can by downloading the keys and checking out the WoT for all received mailing list traffic etc? This would cleary result in a much bigger key ring.

For the inbound processing of mail I have the following automated processes: - -- Messages is downloaded and checked to see if it is a PGP Message (This is handled by the mailers filters). - -- If the message is signed the keyid of signature is extracted from the sig-block and a lookup is performed on the index table for both the users pubring & sig_cache. - -- If the key is not found in either then the message is placed in a queue and a keylookup thread is spawned. - -- There is a setup for which servers and how many to try when doing the lookups. - -- If no key is found on the servers then a canned e-mail message is sent to the sender requesting his keys. The message is taken out of the queue, marked that no key was found and that a request had been sent out. - -- If a key is found it is added to the key cache (sig_cache.pgp). Then normal sig verification is performed. - -- After X amount of hits on a key in the cache the key is flagged as a commonly used key for the user so he can pursue authenticating the key (no sense in going through a lengthy authentication procedure for a key that is only used once). - -- Attached keys are detached from messages and stored in new.pgp keyring (auto adding of keys to ones keyring is a Badthing (TM) ). - -- Encrypted messages are decrypted. All PGP output is appended to the bottom of the message so the info is there when the user opens the message. If a message is in MIME format then the below is appended as MIME attachments using text/X-PGPCheck MIME type. A sample is provided below: - -------------------------------------------------------------------- MR/2 PGP Signature Check 13 Oct 1997 12:19:55 - -------------------------------------------------------------------- File has signature. Public key is required to check signature. Key matching expected Key ID 142DD151 not found in file 'd:\pgp\pgp263a\pubring.pgp'. WARNING: Can't find the right public key-- can't check signature integrity. Plaintext filename: WHGIII\34425839 - -------------------------------------------------------------------- MR/2 PGP Signature Check [Secondary Keyring] 13 Oct 1997 12:19:55 - -------------------------------------------------------------------- File has signature. Public key is required to check signature. . WARNING: Bad signature, doesn't match file contents! Bad signature from user "Ian Brown <Ian.Brown@ncl.ac.uk>". Signature made 1997/10/13 15:15 GMT using 1024-bit key, key ID 142DD151  WARNING: Because this public key is not certified with a trusted signature, it is not known with high confidence that this public key actually belongs to: "Ian Brown <Ian.Brown@ncl.ac.uk>". Plaintext filename: WHGIII\34425839 PGPRC=1 PGPRC2=1

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Also logging of e-mail addresses that do not use PGP cuts down on the number of lookups needed

Good optimisation. It sounds really as if your OS/2 setup is more advanced than a lot of other stuff around.

- -- For the outbound messages the following procedures are in place: - -- All messages are signed with the user having an option of disabling this signature either on a per message basis (through the use of a message template at creation time) or default conditions can be set in the filter no to call the signing script (things like don't sign messages to majordomo, or messages going to remailers, ...ect) - -- Outbound messages can be flagged for encryption on a per message basis (through the use of a message template at creation time) or default conditions can be set in a special default.ndx file used by the encryption script. - -- The encryption script first extracts all the e-mail addresses from the To:, Cc:, & Bcc: lines. - -- It then does a lookup on the default.ndx table. This is where several issues are resolved. 1) No key for address. An address can be flagged as a no-encrypt address. This is mostly for mailing lists and receivers that do not use PGP. 2) Default key for address. An address can be flagged as encrypt and the keyid for that address is included in the entry for that address. This handles things like userid does not match the e-mail address for the person you are sending to (change of address, ect...). Also the issue of multiple keys having the same e-mail address are handled (their can be 5 keys all with the address john_doe@domain.com in the userid fields but only one is the real john_doe@domain.com that you are talking to). 3) Always encrypt flag. You can flag an address to alway encrypt too regardless of wether the message was flagged for encryption at creation time. (hmmmm starting to get into the realm of policy enforcement here <g>). - -- Unless an address is flagged as no-encrypt then a lookup on the keyring indexes for both the pubring and crypt_cache are performed. - -- If and address is not found then a keyring lookup is performed. A separate cache is kept for the encrypted keys and a similar process of flagging frequently used keys is in place as with the sig_cache. - -- now that all the addresses are processed 3 copies of the message are created: 1) Encrypted message. This message is sent to all the addresses where valid keys have been found. 2) Plain Text message. This message is sent to all addresses where they have been flagged no-encrypt in the default.ndx. 3) Error message. This message is returned to the message editor and the user is informed why the message could not be encrypted and then it is up to him to resolve the problem. Most common errors are no key found for the address and multiple keys with the same address found. Both these conditioned can be resolved by making the proper entries in the default.ndx file. 3A) There is a setting flag that tells the script not to split the message as above and error the complete message unless all addresses can be encrypted to. 3B) their is an exception option on 3A where a split message is not in error if the only addresses with no_keys are flagged as public distribution (mailing list, newsgroups, ...ect). 4) BCC messages. Bcc's create a unique problem to the encrypt to multiple recipients function. Because of the format of the encryption block the list of keys used to encrypt is known to all who care to look. This goes against the purpose of a BCC which is to hide a recipient from the rest. In this case I create a separate message for each BCC and encrypt that message with only the key for the BCC recipient. 5) All split messages contain a X-Distribution list containing all the e-mail addresses that the messages was sent to (minus the BCC's of course). I have allot more goodies implemented and/or working on but that should be enough for one message (direct keyring manipulation, remailer support, stamper support, PGP/MIME, balanced b-tree as keyring, ...ect). Much of the optimization work I have been doing is for server side processing useing very large keyrings (+20Mb) but that is another thread in itself. Plus I have a PGP GUI which has many other features for key management & WOT not practical for the automated processing code.

My setup is GNU emacs with Pat LoPresti's mailcrypt.el PGP and remailer support lisp extension for emacs RMAIL and emacs GNUS (newsreader). I love it to bits. It is totally excellent. It doesn't have a couple of your optimisations, but other than that it's pretty good. When you send messages, if you don't have the key it will fetch it for you by trying keyservers, then finger user@domain. It can snarf keys out of mail messages, paste keys into them, sign, encrypt, check signatures, use remailers (type I and mixmaster).

Sounds good except the retrieval of keys from the finger. This is a serious weakpoint in your security. Say you have Adam who wishes to communicate with Mary. He get's Mary's key from her .plan file via finger. Eve has control of the server and replaces Mary's key with her own. Now you encrypt message to Mary but you are using Eve's key. Eve decrypts the message re-encrypts with Mary's and neither of you are the wiser. This is also a weakness in the distributed key approach as it presents a single source of failure unless some type of redundancy is built in. I know that there are many issues involved in this and probably should be spun off into a separate thread if you are interested in pursuing it (too many disjointed subjects in one thread tends to become confusing). - -- - --------------------------------------------------------------- William H. Geiger III http://www.amaranth.com/~whgiii Geiger Consulting Cooking With Warp 4.0 Author of E-Secure - PGP Front End for MR/2 Ice PGP & MR/2 the only way for secure e-mail. OS/2 PGP 2.6.3a at: http://www.amaranth.com/~whgiii/pgpmr2.html - --------------------------------------------------------------- -----BEGIN PGP SIGNATURE----- Version: 2.6.3a Charset: cp850 Comment: Registered_User_E-Secure_v1.1b1_ES000000 iQCVAwUBNEKmhI9Co1n+aLhhAQGgfQP/ZnRMzHAFSgfREts8Op5P+JHfRJHG5khl pUexNZh+VmGpuEkKVMCcIVvYJrICWop7XSYtnI6W0mKd3E2TppVgOplpOvnsHVCv cp1hS8a9MfkBns+Jf7xGG4Z2V3crqGP5ZpcF/PR8Yj8o9wHwx5YoqSLYnF5VTzVM OevaTH+8vJE= =VZeI -----END PGP SIGNATURE-----