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README.smime

SMIME TOOL (merged with ZXID.org project since 2009)
29.10.1999, 17.11.1999, Sampo Kellomaki <sampo@iki.fi>

NOTE: This is still highly experimental code and build system has not been
      perfected yet. No Windows build is known to exist (contributions?).

OFFICIAL WEB SITE
	http://zxid.org/Net_SSLeay/smime.html

BUILDING

	(build and install OpenSSL-0.9.4, from www.openssl.org)
	tar xzf smime-0.7.tgz
	cd smime-0.7
	cons smime        # get cons from http://www.dsmit.com/cons/
	cons SMIMEutil.so # build the perl module (optional)
	./smime -help     # shows quick usage
	./smime -dv ../smime-0.7.tgz
	    (cut my certificate and distribution signature from the web
	     site and paste to stdin)

TUTORIAL PART 1: SIGNING AND ENCRYPTING

	First you need to have certicate and private key in pem format. To
	produce them, use openssl tool or export them from your browser.
	I illustrate the latter method first, because I'm going to use
	Netscape browser for interoperability testing later. You can
	peek at TUTORIAL PART3, Key generation if you need to do this
	yourself.

	- Go to security info dialog in Netscape browser.
	- From Certificates-Yours export your certificate (if you
	  don't have a certificate installed yet, read the FAQs and mailing
	  list archieves at www.openssl.org), save it as me.p12. It
	  will ask for password to protect your private key.
	
	  openssl pkcs12 -clcerts <me.p12 >me.pem
		- it will ask for the password to open your private key and
		  then asks you to invent a new password that will be
		  used to protect your private key in pem format

	  more me.pem
	
	You should see something like this:

Bag Attributes
    friendlyName: your@email.com
    localKeyID: F3 85 A8 4B DA 39 B6 40 6B D6 20 01 39 46 6A 94 47 9D 2C 0F
Key Attributes: <No Attributes>
-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: DES-EDE3-CBC,541E04862A13F6B1

8+2vo6Iz49uj/Mf31JTgaRuIq9ueHsknsHXhmXp7s1BmS8xulT22Zzpdh6g1yqAO
(snip)XeQsZrWykdWvN2qGu/cNa2HnUQAG0p25tNZ3CKmqpJBVg0RXr20JlQ==
-----END RSA PRIVATE KEY-----
Bag Attributes
    friendlyName: your@email.com
    localKeyID: F3 85 A8 4B DA 39 B6 40 6B D6 20 01 39 46 6A 94 47 9D 2C 0F
subject=/C=PT/L=City/O=Company/OU=Dept/CN=Your Name/Email=your@email.com
issuer= /C=PT/L=City/O=Your CA/OU=Personal Certs/CN=End user CA/Email=certifier@ca.com
-----BEGIN CERTIFICATE-----
MIIDEzCCAnygAwIBAgIBAzANBgkqhkiG9w0BAQQFADCBlTELMAkGA1UEBhMCUFQx
(snip)Tj0JYGZMzSUfzOG3wajK6B39d6EyXK8=
-----END CERTIFICATE-----

	Ok. Now you are all set to use smime tool. First lets create
	simple mime entity (see RFC1521 for definition):
	
	  echo foo | ./smime -mime text/plain | tee foo.mime
	
Signing
	Now, let's sign it:

	  ./smime -s me.pem password <foo.mime | tee foo.smime

	And send it:

	  ./send.pl 'Sig test' your@email.com your@email.com <foo.smime

	Now go to your email reading software (Netscape Communicator suggested
	for this exercise) and read the mail you just sent. It should display
	as signed. In the previous command the second argument is the
        From: header which must match friendlyname/EMAIL in me.pem

	You can repeat this success using following pipeline:

	  echo foo | ./smime -mime text/plain | ./smime -s me.pem password \
	  | ./send.pl 'Sig test' your@email.com your@email.com

	(Note how \ is used for folding the lines. In reality you should
	 type all the stuff in one line.)

Clear signing
	The previous method produces a base64 blob that you probaly would not
	like to send to a news group. Clear signing allows mail to be read
	even if the reader is not S/MIME aware:

	  echo foo | ./smime -mime text/plain | ./smime -cs me.pem password \
	  | ./send.pl 'Sig test' your@email.com your@email.com

	Note how the message has "foo" visible. Now go read this with your
	mail reader. It should also display as signed. If not, then its
	possible that canonization was not correctly done. That might even
	be an error in my part.

Encrypting
	To encrypt you need to know recipient's cert. Here I use our own
	because its by definition already installed in our browser.

	  echo foo | ./smime -mime text/plain | ./smime -e me.pem \
	  | ./send.pl 'Enc test' your@email.com your@email.com

	Now you should be able to read your mail (it may ask for a password
	to open your private key) and see the message in plain text, but
	marked as encrypted.

Signing and Encrypting
	Next we'll first sign a message and then wrap it in encryption. This
	is the usual way and hides the signatories from eavesdroppers:

	  echo foo | ./smime -mime text/plain | ./smime -cs me.pem password \
	  | ./smime -e me.pem | ./send.pl 'test' your@email.com your@email.com

	Again your mail reader should show the message marked as
	Encrypted and Signed.

Encrypting and Signing
	The other way is to first encrypt and then sign the encrypted
	message. This might be useful in some automated context where a robot
	would verify the signature but the robot should not be allowed to see
	the message:

	  echo foo | ./smime -mime text/plain | ./smime -e me.pem \
	  | ./smime -cs me.pem password \
	  | ./send.pl 'Enc test' your@email.com your@email.com

	Now Netscape shows two icons: one saying "Signed" and placed near
	the headers. Other icon that says "Encrypted" appears in the
	content area.

	In fact S/MIME specification allows arbitrary nesting of encryptions
	and signatures, what ever your application may need.

Multipart content
	Now for the final part that is not really S/MIME specific, but
	nice to have. You can first compose a normal mime multipart message,
	possibly even containing some encrypted components and some not.
	Try this:

	  echo bar | ./smime -m image/gif some.gif \
	  | ./smime -cs me.pem password | ./smime -e me.pem \
	  | ./send.pl 'Enc test' your@email.com your@email.com

	Now you should see signed and encrypted message with an image
	attached. The multipart functionality implemented by -m is very
	basic and by no means anything generic. Its only a demonstration.

TUTORIAL PART 2: DECRYPTING AND VERIFYING SIGNATURES

Decrypting
	To demonstrate decrypting, I'll cut the mail from the loop. Basically
	I'll demonstrate introperability with myself. If you want to try
	interoperability with Netscape, you can use Netscape to send mail
	and grab it from mail spool and then feed it into pipeline. As this
	is a bit messy and might involve editing the file manually, I
	wont go into that now. Here's a simple encryption - decryption:
	
	  echo foo | ./smime -mime text/plain | ./smime -e me.pem \
	  | tee foo.p7m | ./smime -d me.pem passwd

	foo wrapped in mime headers should come out. I also used tee(1) to
	put the encrypted form in a file in case I also want to verify
	it with Netscape

	  ./send.pl 'Enc test' your@email.com your@email.com <foo.p7m

	or in qmail

	  /var/qmail/bin/qmail-inject your@email.com < foo.p7m

        This is most convenient method because it allows you to import
	certificates belonging to others than yourself and still
	deliver mail to yourself. You want this, because you will soon
	discover that Netscape can hold in its certificate database
	only one certificate per email address (or is it distinguished name?)
	and if that one "slot" is occupied, say, in "People" section, then
	you can't import it any more to "Yours" section. Hence the solution
	is to use different email address (and friendly name) every
	single time.

Verifying signature
	Due to somewhat incomplete nature of OpenSSL-0.9.4 PKCS7 signature
	verification code, I have implemented my own signature verfication
	scheme that works in five steps

		1. find out who signed the message
		2. verify message signature using signer's certificate
		3. find out who certified the signer's certificate
		4. verify signer's cert using certifier's cert
		5. repeat 3. & 4. until at root of the chain

	This has the advantage that there are less obscure stuff and
	assumptions hidden inside the program, i.e. user must understand
	what signature and certificate verification is all about and
	you get to observe every step of the way. The down side is that
	its less automatic. In my particular application this does not
	happen to be a problem because I have out of band information
	about who is supposed to have signed what.

	Here we go: lets produce a signature to play with

	  echo foo | ./smime -mime text/plain | tee foo.mime \
	  | ./smime -s me.pem password | tee foo.p7m
	
	Now see who signed it
	
	  ./smime -qs < foo.p7m
	
	Now I assume that I have some way of finding the certificate using
	the issuer DN and serial number returned in the previous step. These
	two pieces of information constitute unique ID for a certificate.
	Perhaps I keep my certs in LDAP or some other database. Anyway,
	assume the certificate is found, then
	
	  ./smime -v me.pem <foo.p7m | tee foo2.mime
	  diff foo.mime foo2.mime   # just to check!
	
	Note that diff may show white space differences (try diff -b) because
	line endings in your mime message were canonized to CRLF for signing.
	This is mandated by S/MIME specification.

	Now proceed with verifying the certificate:

	  ./smime -qc <me.pem

	Now out of band means are used to find the signer's certificate. Then
	to check that the signature matches:

	  ./smime -vc ca.pem <me.pem

Verifying clear signature
	(does not currently work :-(

Under construction: chain verification (does not currently work)
	mkdir certs
	cd certs
	cp ../me.pem .
	../hash-certs.pl *.pem
	cd ..
	echo foo | ./smime -mime text/plain | ./smime -s me.pem password \
	| ./smime -v

TUTORIAL PART 3: A KEY GENERATION METHOD

Bootstrapping a simple public key infrastructure

	Suppose entity M is funding projects and needs to have all project
	leaders (Ps) sign a contract specifying responsibilities. M
	distributes a simple application that incorporates the smime tool. Ps
	use the application to sign the contracts and send them electronically
	to M. If irregularities develop, M sues P to court and uses the
	digitally signed contract as evidence. For this to work

		I.  M must convince the court that the system does not have
		    technical flaws that could work in his favor. This proof
		    is much easier with digital signatures than with systems
		    that depend on procedural integrity (e.g. passwords over
		    SSL protected connection may prove at the moment the
		    intention of P, but when document is recovered from backup
		    10 years later, all procedural proofs vanish)
		
		II. P's signature must be as valid as paper and ink
			1. P's real world identity must be connected to
			   digital signature
			2. P must have understood what it means to sign
			   contract digitally
			3. P must have sufficient integrity or the system
			   must technically guarantee that P's private
			   key could not have been used by any one else
			4. P must have acted by free will and in full powers
			   of mind
			5. law must not prohibit digital signature

	M needs to establish a simple public key infrastructure. I propose
	that the application generates key pairs for P's and sends
	certification requests, further, it also prints the certification
	request in paper form including,

		- fingerprint of public key (as number and as bar code)
		- full dump of public key and all attributes appearing
		  in the certification request
		- legal language to guarantee 2. & 3. (on point 3 we rely
		  on integrity)
		- details of conventional identification of P
		- space for signature

	With this paper P goes to some commonly agreed and trustworthy
	notary. This could be notary public or it could be some trusted
	administrative organ in P's organization. It could even be M, but
	that would cause a bureaucracy bottle neck at M, and hence increase
	costs of the solution.
	
	P signs the paper and proves his identity in presence of the notary
	who confirms the act. The paper is sent to M. This takes care of
	1. and 4. As paper contract about use of digital signatures now
	exists between M and P, 5. is only of concern if it explicitly
	nullifies such contract (or if court practice still does not consider
	digital signature valid?).

	Finally paper arrives to M where a clerk processes it (the bar
	code helps here). He finds the certification request from data base
	and sees that it matches the paper and issues a digital cerificate
	that is immediately placed on a public server for everybody to
	see. The paper is securely archieved forever.
	
	Once the certificate is publically available, signing and verifying
	contracts using it is trivial and can even be done between P and
	some other party than M (e.g. certificate could be used for email).
	
	However, to bootstrap the system it should, ideally, be possible
	to sign your first contract even without waiting for the
	certification to happen. After all, the impulse	for P to adhere
	to PKI of M came from needing to sign a	contract (dead line for
	research proposals may be very close). The contract would be
	in signed, but not verified status until the certification happens.

	Here the OpenSSL (or PKCS7?) does not serve us well, because it needs
	a certificate even for the signing operation, although common
	sense says that the private key and attributes of certification
	request (ok, you can't know what serial number will be assigned)
	should be enough. I solve this problem by signing the first contract
	with a self signed certificate. Although this is quite suboptimal,
	it allows me to get going without hacking OpenSSL innards too much.
	Only complication arises from needing to establish that also the
	certified public key is able to decrypt the hash of the signed
	material.

Key generation

	Smime tool contains simple key generation command that will
	make certification request as well as self signed cert. This
	is bit simplistic and really geared towards my particular application
	as the X509v3 certificate options are hardwired. Be sure to read
	the source code to check they are the way you want.

	  echo "commonName=Joe Smith|emailAddress=joe@test.com" \
	  | ./smime -kg "description=foo" passwd req.pem >priv_ss.pem

	The stuff that is echoed to stdin is your distinguished name. You
	must use long forms of attribute name and you can only use attributes
	known to OpenSSL.

        *** How to specify cn as needed by SSL certs?

        The req.pem should be sent to certification authority for signing.
        Meanwhile you can use the self signed certificate which was output
	to stdout, here priv_ss.pem. Note that the private key is also
	output to the stdout so do not give that file to anyone. If you need
	to give the certificate, you should edit a copy of priv_ss.pem
	and remove the private key.

	To be able to import your private key and certificate to Netscape
	you can use

	  ./smime -pem-p12 you@test.com passwd pw-for-p12 <priv_ss.pem >me.p12

	The first argument (the email address) is the friendly name. Netscape
	appears to match this against From mail header when verifying
	signatures. For minimum troubles you should keep this equal to
	emailAddress field of your certificate.

Being a certificate authority

	Once you have made your req.pem, you can send it to some commercial
	certification authority or you can just be your own. The CA
	functionality of smime tool is not very complete. Basically
	it allows you to do the crypto part (signing certificate request with
	CA's private key) but you must manually do book keeping to ensure
	uniqueness of serial numbers and to make sure you do not issue the
	same certificate twice, etc.

	Here's how you'd sign a request (you probably used -kg to make
	the CA's certificate):

	  ./smime -ca ca-id.pem very-secret 1 <req.pem >cert.pem

	The number one is the serial number. As I said, you should do
	bookkeeping to ensure you never reuse a serial number. Many
	systems depend on being uniquely able to identify certificate
	by its issuing authority and serial number. A certificate
	authority that can not guarantee uniqueness of serial numbers is
	not trustworthy.

	Please note that the -ca hard wires all X509v3 options and extensions.
	Be sure to read the source to check they are the way you want them.

TUTORIAL PART 4: SIGNING AND VERIFYING SOFTWARE DISTRIBUTIONS

	smime tool has detached signature feature which is meant for
	signing and verifying software distributions. Here's how. First
	make yourself an identity

	  echo 'commonName=my dist key|emailAddress=you@test.com' \
	  | ./smime -kg '' pw dist-req.pem >dist-id.pem
	
	Now open dist-id.pem in editor and save the certificate part as
	dist-cert.pem. Pubish dist-cert.pem on your web site.

	Then sign your software package

	  ./smime -ds dist-id.pem pw <your-dist-1.00.tgz >your-dist-1.00.sig

	I suggest convention of naming the signature file with same name
	as the tarball, but extension `.sig'. Now put the .sig file
	available where ever you put your tarball. You should also publish
	it on your web site so people can get it even if they forgot to
	download the .sig file.

	Or you could produce a combination signature and certificate file
	and put that available on your website

	  ./smime -ds dist-id.pem pw <your-dist-1.00.tgz \
	  | cat - dist-cert.pem >your-dist-1.00.sigcert

	To verify a distribution signature one would say 
	
	  ./smime -dv your-dist-1.00.tgz
	    (cut certificate and distribution signature from the web
	     site and paste to stdin)

	The dv looks for the -----BEGIN/END CERTIFICATE----- separator to
	figure out where the certificate ends and signature starts.

	If you already had the .sig or the certificate you could just say

	  cat dist-cert.pem your-dist-1.00.sig | ./smime -dv your-dist-1.00.tgz
	
	(OK, PGP already exists to do this stuff, but I always found it
	 quite messy to deal with detached signatures in PGP. I'm sure
	 poor usability leads to less people verifying the signatures.)

SMIMEUTIL LIBRARY AND PERL MODULE

	The smimeutil library is documented in smimeutil.h, see smime.c
	for some examples of usage. The SMIMEUtil:: perl module is
	not currently documented. For usage examples see test.pl.

CAVEATS
	For signing to work correctly, your mime entity must be canonized
	the same way as the recipient will canonize it. In general this
	means that you must use CRLF as line termination and must include
	all headers.
	
	If you are clear signing, then you may want to consult RFC2311 for
	some ways the message might get ruined (e.g. changes in whitespace).
	In my experience most important requirement seems to be to not
	use any trailing whitespace. YMMV.

	For signatures to verify correctly, the From: header of the mail
	must be equal to "friendlyname:" and EMAIL fields in your cert.

	When encrypting, do not forget to wrap your message in mime entity.
	If you don't, ./smime -d will silently return emptiness, Netscape
	reports "improperly formatted DER-encoded message". This
	will _not_ work:

	  echo "foo" | ./smime -e me.pem | ./smime -d me.pem secret  # WRONG!

SECURITY CAVEATS
	Passing passwords on command line is insecure. The smime tool is
	intended more as a demonstration than a production tool. See
	pass-password.pl for an example how to use file descriptor to
	pass the passwords more securely.

	smimeutil.c compiles by default to use DES-EDE3-CBC cipher which
	is not known by export versions of many browsers. See around
	line 400 in smime-enc.c if you need to change this. Be ware that
	RC2-40-CBC can be cracked in real time by trivial resources.
	Never-the-less its the only cipher that interoperates with all
	versions of browsers.

	Randomnumbers are not (yet) initialized as they should.
	
	Certificate verification scheme puts the burden of verification
	on user. For example, the user must notice if purported CA certificate
	has X509v3 attribute that forbids it from being CA cert.

TIP
	You can use Netscape to encrypt and sign messages and then look
	at them in mail spool. This way you see their raw structure before
	any mail reader gets to interpret it. This is the best way to
	debug differences between what you produce and what is presumably
	standards compatible.

TO DO
	Parsing mime messages in robust and fully correct way

BUGS
	Due to the way the API is defined all stuff is kept in memory. While
	this is simple and easy, you might get into trouble with large files.
	I'd say the memory consumption will not exceed five times the file
	size, but don't bet on it.

	Signature verification in perl module still needs some work.

SEE ALSO
	RFC1521 (MIME)
	RFC2111 (S/MIME v2)
	*** RFCXXXX (S/MIME v3)
	http://www.openssl.org
	http://zxid.org/Net_SSLeay/smime.html  (this stuff)

USAGE
	(reproduced from ./smime -help)
	
	./smime -cs private password <mime-entity >smime  # clear sign
	./smime -cv cert <smime-entity >data              # verify clear sig
	./smime -ds private passwd <file >smime-sig       # make detached sig
	./smime -dv file <smime-sig-entity                # verify detached
	./smime -s  private password <mime-entity >smime  # sign
	./smime -qs <smime-entity >signing-cert-info      # find out who signed
	./smime -v cert <smime-entity >signer-dn          # verify signature

	./smime -vc cacert <cert                          # verify certificate

	./smime -e public <mime-entity >smime-ent         # encrypt
	./smime -d private password <smime-entity >mime   # decrypt

	./smime -qr <req.pem    # Query all you can about request
	./smime -qc <cert.pem   # Query all you can about certificate
	./smime -ca ca_cert passwd serial <req.pem >cert.pem     # sign a req

	./smime -p12-pem p12pw pempw <x.p12 >x.pem  # convert PKCS12 to pem
	./smime -pem-p12 frindly@name.com pempw p12pw <x.pem >x.p12

	./smime -m type1 file1 type2 file2 type3 file3 <text  # make multipart
	./smime -m image/gif foo.gif <message | ./smime -s private pass >smime

	./smime -kg attr passwd req.pem <dn >priv_ss.pem  # keygen

	./smime -base64 <file >file.base64
	./smime -unbase64 <file.base64 >file
	./smime -mime text/plain <file >mime-entity
	./smime -mime_base64 image/gif <file.gif >mime-entity
	./smime -split dirprefix <multipart         # splits multipart
	./smime -base64 <in | ./smime -unbase64 >out
	./smime -cat <in >out   # copy input to output using slurp and barf

	./smime -kg 'description=Test' secret req.pem <me.dn >ss.pem

--Sampo
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