WebUser Interface: Secure Mail (S/MIME)
Imagine a spy who needs to exchange information with his center securely, using some secret key. That key must change frequently to ensure that the time needed to "break the key" is much larger than the "lifespan" of the information encrypted with that key. The center has to send those new keys to the spy (or vice versa), but those keys can be intercepted, and anyone who succeeds in intercepting the key will be able to decrypt all messages they send.
The Public Key technology uses pairs of specially generated keys. Both keys are very large numbers: they have 512 bits in length (approximately 60 decimal digits) or more. The special method used to generate those key pairs and the method used to encrypt information with those keys ensures that the message encrypted with one key can be decrypted with the other key. One key is called the "Private Key", the other key is called the "Public Key".
The PKI algorithms ensure that any data encrypted with the Public Key can be decrypted with the Private Key, any data encrypted with the Private key can be decrypted with the Public Key, and that it is extremely difficult to calculate the Private Key if the Public Key is known. Please note that messages encrypted with the Public Key cannot be decrypted with the same Public Key - they can be decrypted only with the Private Key.
Now we can see how this technology can be used by a spy, or any other party that needs to exchange information securely:
In real applications, PKI is not used to encrypt actual information. Instead, a random "regular key" ("shared secret","password") is generated, actual information is encrypted using that shared secret, and PKI is used to encrypt that "shared secret" key. The encrypted "shared secret" key is appended to the actual information. The recipient uses its Private Key to decrypt the "shared secret", and then uses that "shared secret" to decrypt the actual data, using regular, "symmetric cryptography".
This method is used to decrease the amount of PKI computations (shared key is usually much smaller than the actual information), since PKI algorithm are much more complex than symmetric-key algorithms.
When it is said that the information is encrypted using 40 bit, or 56 bit, or 128 bit keys, it means that the random "shared secret" key used had this length - the PKI keys have much higher length. It is much easier to break a 40-bit "shared secret" key used to encrypt data, than to break a PKI key used to encrypt that "shared secret". But "shared secret" keys are generated at random for each transaction, so if someone breaks the "shared secret key" used for any transaction, only that transaction will be compromised (decrypted), because other transactions with the same PKI keys will use different "shared secret" keys.
The method with 2 keys (PKI and "shared secret") allows a sender to send an encrypted message to several recipients at once. A message is encrypted using a random "shared secret" key, and then PKI is used to encrypt that "shared secret" several times, with Public Keys of all recipients. All encrypted "shared keys" are appended to the message, and each recipient can find the "shared secret" encrypted with its own Public Key, decrypt it with its Private Key, and use the decrypted "shared secret" to decrypt the actual information.
Digest is a relatively short (16-40 bytes) number with a "checksum" of the message. The algorithms used for "digesting" ensure that it is very difficult to compose 2 different messages that would have the same digest values.
To sign a message, the sending software:
The receiving party uses the sender's Public key (it is known to the receiving party) to decrypt the message digest, calculate the message digest itself, and compare the decrypted and calculated digests. If they match, the message has not been altered, and it was really sent by the party that has the proper Private Key.
In our spy example, a third party won't be able to send a message pretending to be the Center, because it does not know the Center Private Key. And if the third party encrypts the digest with some other Private Key, the signature verification will fail, because the spy will try to decrypt the digest with the Center's Public Key, and the resulting garbage will not match the calculated message digest.
To solve this problem, the Public Keys are not distributed in the "raw form". Instead, they are distributed embedded into Certificates. A Certificate contains the following data:
Certificates are issued by a Certificate Authority - some party that all parties choose to trust. All parties should know the Public Key of the Certificate Authority. Modern Internet applications (browsers, mailers, etc.) have a built-in list of Trusted Authorities (including VeriSign and other similar companies), and have the Public Keys of those Trusted Authorities built-in.
When a certificate is received, the receiving party can verify if it has been issued by a "trusted authority": it checks if the "issuer" name in the Certificate is one of the "Trusted Authorities", and uses the already known Public Key of that Authority to verify the Certificate signature. If the signature is verified, the party can trust that the Public Key in the Certificate really belongs to the party specified in the Certificate Subject.
Very often an intermediate Certificate Authority is used. For example, a corporation can get a Certificate issued by a Trusted Authority, and then it can act as a Certificate Authority itself, issuing certificates for its employees. To enable verification of such a certificate by any third party, the Certificates issued by an Intermediate Certificate Authority are sent together with the Intermediate Certificate Authority own Certificate. The receiving party first checks that the Certificate is really issued by that intermediate Authority (by using the Public Key from its Certificate to verify the signature in the sender Certificate), and then it checks that the intermediate Authority is what it claims to be (by verifying its Certificate using the known Trusted Authority Public keys).
CommuniGate Pro stores the Certificate in the Account Settings (as the "userCertificate" element), and also it copies the Certificate into the Directory - if the Directory Integration is enabled.
CommuniGate Pro stores the Private Key in the Account Settings, but it encrypts the Private Key with a "Secure Mail Password". To use any of the Secure Mail functions, you should enter the "Secure Mail Password" to let the server read and decrypt your Private Key.
Note: The server does not store your Secure Mail Password anywhere. If you forget the password, you will need to obtain a new Private Key and Certificate. This means that your will not be able to decrypt any message encrypted with your old Public Key. Neither your System Administrator nor Stalker Software will be able to help you get those messages back.
Note: While it is very important to remember your Secure Mail Password, it is not too difficult to do: the Secure Mail Password can be a word or a phrase (up to 100 symbols), in any language.
You can use your regular E-mail client (such as Microsoft® Outlook or Netscape® Messenger) to obtain
a personal Private Key and Certificate (also called "Digital ID"). You can then export that "Digital ID" to a
.pfx or .p12 file - a so-called PKCS#12-formatted file. In order to protect your data, the E-mail
client will ask you for a password, and will encrypt the exported information with that password.
Note: while the file format supports non-ASCII symbols in a file password, you should use ASCII symbols only, as many E-mail clients (including Outlook) do not process national symbols correctly.
Connect to the Server using the WebUser Interface, and open the Settings section. Click the Secure Mail link to open the page that contains the following fields:
Note: If you do not see the Secure Mail link on your Settings pages, it means that your Account or Domain has the S/MIME service disabled.
Enter the name of the saved .pfx or .p12 file or use the Browse button to select the file on your workstation disks. Enter the File Password you used when you created that file.
Enter the password that will become your Secure Mail Password - this password will protect your Private Key on the CommuniGate Pro server. Enter this password twice, into two fields, and click the Import File Data button. If you have entered the correct File Password, the Certificate and Private Key information will be stored in your CommuniGate Pro Account settings.
Alternatively, you can ask the CommuniGate Pro server to generate a Private Key and a Certificate for you. Use the Generate Key And Certificate button:
As when importing Key and Certificate from a file, you need to specify the password (twice) that will will become your Secure Mail Password.
The generated Certificate will be issued for the E-mail address you have specified as your From address in the WebUser Interface Settings, but only if that address points to your CommuniGate Pro account. Otherwise, the Certificate is issued for your CommuniGate Pro Account address.
The generated Certificate is signed with the CommuniGate Pro server certificate.
The Secure Mail page now shows your Certificate data and the size of the Private Key.
To change your Secure Mail Password, enter the new password twice into the Modify Secure Mail Password panel fields and click the Modify Password button.
To store your Key and Certificate information in a file on your workstation disks, click the Export Key and Certificate link. A panel will open in a new window:
Enter the password to be used to encrypt your Key and Certificate information in the file (you need to enter it twice), and click the Export button. Your browser should ask you where to save the CertAndKey.pfx file (you can rename it).
IF you decide to remove your Private Key and Certificate, you need to have their copy in a file. This is done to ensure that you can restore this info if you removed the Key by mistake. Remember that if you remove the Private Key completely and do not have a file to restore it from, all encrypted messages sent to you will become completely unreadable.
To remove the Key and Certificate, enter the name of the file that has the your Key and Certificate and the file password, and click the Compare with File and Delete button. CommuniGate Pro will decrypt the file using the supplied password and it will compare it to your current Private Key. If the Keys match, the Private Key and Certificate are removed from your Account Settings.
To activate your Private Key again, you need to enter the Secure Mail Password on any of the CommuniGate Pro WebUser Interface pages that displays the S/MIME Key Activation panel:
If the information cannot be verified with any signature, an error message is displayed.
When an Address Book is displayed, the [@] marker indicates the entries that have known (stored) certificates. You can send encrypted messages to those addresses.
Recipients of your Signed message will be able to verify that the content has not been altered, and they will be able to store your Certificate and later send you encrypted messages.
If your Private Key is unlocked, you will see the Send Encrypted checkbox on your Compose page. Select this checkbox to encrypt your message. If you send a message with attachments, the entire content of your message, including all attachments, will be encrypted with the recipients Public Keys (taken from their Certificates), and with your own Public Key. As a result, if a copy of the encrypted message is stored in your Sent mailbox, you will be able to read (decrypt) it.
If you select both Send Signed and Send Encrypted options, the message will be composed as a Signed message, and then the entire content (including the message headers and your signature) will be encrypted.
Use the Encryption Method WebUser setting to specify the encryption "cipher".
You need to activate (unlock) your Private Key first. With the Private Key unlocked, the WebUser Interface module tries to decrypt all encrypted messages with your Private Key. If it succeeds to decrypt the message, the message content is displayed:
When you want to keep the message in your mailbox, but you want to keep it in the decrypted form, click the Decrypt button. The Server will try to decrypt the encrypted message. If it succeeds, it will store the decrypted message in your mailbox and will remove the original encrypted message.