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Figure 89: Fetchmail new account
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Figure 90: System runtime control
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Figure 91: Compose test email
Figure 92: Extract text
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The SMTP helo/ehlo name is the hostname the SMTP server sends with the
SMTP EHLO or HELO command (the Ciphermail gateway uses the HELO or
EHLO command when sending email to another email server). Some email
servers check whether the helo/ehlo name is equal to the reverse IP lookup
(with a reverse IP lookup the name is retrieved that belongs to the IP address)
and if the names do not match they will flag the email as spam.
If the Ciphermail gateway is used to directly send email to external recip-
ients (i.e., outgoing email is not relayed through an external relay host) the
gateway should be setup with the correct helo/ehlo. The SMTP helo name
should be equal to the reverse lookup of the external IP address.
If the external IP address is not known and the Ciphermail gateway uses
the same IP address as the web browser, the external IP address and host-
name (reverse IP) can be retrieved using on-line services likehttp://www. TheIPaddressshownistheexternalIPaddress.
The shown hostname (the reverse IP lookup) should be used for the SMTP
helo name. If the hostname of the Ciphermail gateway is set to the external
hostname, the SMTP helo name can be left empty because the SMTP helo
name will then be equal to the gateway hostname.
Checking the HELO/EHLO name whether the HELO/EHLO name is cor-
rectly setup can be checked using the helo check services fromhttp://cbl.“”.
The email will be immediately bounced. The bounce message contains the
HELO name used by the gateway.
<>: host said:
550 HELO for IP was ""
(in reply to RCPT TO command)
Where is the external IP address of the gateway (IP address
will be different for every server) and “” was the HELO name
used by the gateway.
B SASL authentication
SMTP client authentication is not enabled by default. SMTP client authenti-
cation can be enabled by adding the following lines to the postfix main config
using the “MTA raw config” page (see4.4):30
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/smtp_client_passwd
smtp_sasl_type = cyrus
New SASL credentials for an SMTP host can be added by clicking “add
password”. This opens the “Add SASL password” page (see figure93). If “mx”
The main config that comes with Ciphermail gatewayalready contain these lines. They are
however commented out.
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is selected the MX-records of the server are used instead of the IP address of
the server (A-record). In most cases the IP address of the server should be
used and “mx” should therefore not be selected.
Figure 93: SASL add password
Gmail example: as an example the following part will explain how to use
the Gmail SMTP servers as an external relay host (i.e., email sent to external
recipients will be relayed via Gmail). For SMTP authentication Gmail requires
aTLS protected connection. TLS and sasl authentication should therefore be
enabled by adding the following lines to the postfix main config file using the
“MTA raw config” page (see4.4):
smtp_tls_security_level = may
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/smtp_client_passwd
smtp_sasl_type = cyrus
smtp_tls_CApath = /etc/postfix/certs/
smtp_sasl_security_options =
The “External relay host” should be set to “” and the port to
“587” (see figure94).
Figure 94: Gmail external relay host
The SASL password for server “” and port “587” should be
set. Theusername should be settotheGmail username(theusername should
include and password (see figure95).
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Figure 95: Gmail SASL password
C Content and virus scanning
A content scanner can be used in combination with Ciphermail gateway to
selectively force encryption when a message contains certain keywords (for
example a“Social Security Number”). A typical setup of a content scanner and
an encryption gateway can be see in figure96.
Figure 96: Content scanning
Ciphermail gateway with content scanner:
1. User sends unencrypted message.
2. Exchange forwards message to content scanner.
3. Content scanner detects that the message must be encrypted (for exam-
ple the message contains a SSN).
4. Ciphermail gateway encrypts the message with S/MIME or PDF.
5. Content scanner sends the encrypted message to the recipient.
Most organizations needtoscanall incomingandoutgoing email forviruses.
Atypical setup of anencryption gateway and a virus scannercanbe seein fig-
Figure 97: Virus scanning
Ciphermail gateway with virus scanning:
1. S/MIME encrypted message is received from the Internet.
2. Ciphermail gateway decrypts the message.
3. The decrypted message is scanned for viruses.
4. After virus scanning the message is forwarded to Exchange.
5. User reads the message.
Amore advanced setup is required when email must be encrypted on the
desktop yet all outgoing email must be virus scanned because of corporate
policies. Figure97shows how encrypted outgoing email canbevirus scanned.
Figure 98: Virus scanning with desktop encryption
Ciphermail gateway with desktop encryption and virus scanning:
1. User encrypts message with personal and receivers certificate.
2. S/MIME encrypted message is sent to Exchange.
3. Exchange sends S/MIME encryptedmessageto the Ciphermail gateway.
4. Ciphermail gateway decrypts the message with the senders private key
(the gateway stores a copy of the key) andsends the decrypted message
to the virus scanner.
5. Virus scanner scans the message and if clean it will be sent back to the
Ciphermail gateway.
6. The Ciphermail gateway re-encrypts the message and sends the mes-
sage to the external recipient.
D Cron Expressions
The following cron examples are taken fromhttp://www.quartz-scheduler.
00 12 * * ?
Fire at 12pm (noon) every day
015 10 ? * *
Fire at 10:15am every day
010,44 14 ? 3 WED
Fire at 2:10pm and at 2:44pm every Wednesday in March.
015 10 15 * ?
Fire at 10:15am on the 15th day of every month
015 10 L * ?
Fire at 10:15am on the last day of every month
For more cron examples see the “Quartz Scheduler” website.
E MPA mail flow
The following flow-charts will show exactly how email is processed by the Ci-
phermail gateway.
Figure 99: Start
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