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4.8 SMTP transports

4 MTA SETUP

Figure 15: Header checks

Figure 16: SMTP transports

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5 USERS

Figure 17: Users

5 Users

A user is a sender or receiver of email and is uniquely identiﬁed by his/her

email address. Every user has a set of preferences that determine how email

is handled for that particular user. The users page gives an overview of all the

users (see ﬁgure17).

Speciﬁc userscanbesearched for usingtheﬁlter. Users canberemovedby

clicking the ’cross’ icon orby selecting the users and clicking “delete selected”.

New users can be added by clicking “Add user” on the left hand side menu.

Clicking a user opens the user preferences page (see next section). Internal

users are marked with a green star icon (see “Locality property” on page23

for more info on the difference between internal and external users). Clicking

the user certiﬁcate icon opens the certiﬁcate selection page for the user. If the

user is an internal user, the “Select signing certiﬁcate” page is opened. If the

user is an external user, the “select encryption certiﬁcates” page is opened.

5.1 User preferences

Every user has a set of preferences which determine how email is handled for

that particular user. User preferences caninherit someor all of the preferences

from higher level preferences.

Users inherit their preferences from domain preferences, domain prefer-

enceinherit from theglobal preferencesand theglobal preferences inherit from

the factory preferences:

user domain wild-card domain

global factory.

Thepreferences fora user canbeeditedbyclicking ontheusers email address

(seeﬁgure18). The userpreference pagelinks to sub-pages “select encryption

certiﬁcates”, “select signing certiﬁcate”, “templates” and “global preferences”

which can be used to edit additional preferences. Whether a preference is in-

herited or not is determined by the associated “inherit” checkbox. If checked,

the preference is inherited.

An example of a wild-card domain is *.example which matches test.example.com.

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5.1 User preferences

5 USERS

Figure 18: User preferences

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5.1 User preferences

5 USERS

Sender and receiver preferences Some preferences are only relevant for

the sender of a message and some preferences are only relevant for the re-

ceiver of a message. Most preferences however are relevant for both the

sender and receiver. The MPA mail ﬂow in AppendixE shows exactly when

and how preferences are used by the MPA.

Note: “S” or “R” (surrounded by parentheses) is placed after the property

name to indicate whether a preference is a sender preference or a receiver

preference. Some properties are used as a sender and receiver property. A

property which is used as a sender or recipient property is written as (S | R). A

property whichis usedas a senderand recipient property is written as (S & R).

Message originator The Ciphermail gateway uses the “From” header as the

identity of the sender and not the “envelope sender”. It is important to under-

stand the difference between the from and the envelope sender because the

identity of the sender determines which settings and certiﬁcates will be used

by the sender. Because sender is such a confusing term, the term “originator”

will be used instead when referring to the identity of the sender (i.e., the from

header).

The rationale for using the “From” for the identity of the sender is that the

envelope sender is more or less similar to the postman and is therefore only

responsiblefor themessagedeliveryand not for the message contentwhereas

the “From” identiﬁes the actual originator of the email. The user identiﬁed by

the “From” is responsiblefor the message content. In most cases however, the

envelope sender is the same as the “From”.

Another important reasonwhy thefrom headeris used, is thatS/MIME uses

the from header as the identity of the sender, i.e., an S/MIME client compares

the email address of the signing certiﬁcate with the from header of the mes-

sage. While the identity of the sender is determined by the from header, the

identity of the recipient is determined by the recipient of the SMTP envelope

and not the “To” header.

Next, a brief overview of the all the user preferences will be given.

5.1.1 General

Comment This ﬁeld is a free form text ﬁeld in which the administrator can

add some comments related to this user.

Locality (R) The “locality” of a user can be external or internal. The “locality”

preference is avery important preference becauseit determineswhether email

coming into the gateway should be encrypted or decrypted. If the recipient of

an email is an internal user, the email should be decrypted. If the recipient of

an email is an external user, the message should be encrypted (whether the

message will actually be encrypted depends on other user settings). Typically

users for which the gateway receives email will be internal users (i.e., users

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5.1 User preferences

5 USERS

belonging to one of the relay domains) and all other users will be external

users. The domain of a recipient is based on the SMTP envelope recipient.

The domain of the sender is based on the “From” header3.

Note: becausethelocalityissuchanimportantpreference,itshouldbesetup

correctly. In most installations all domains forwhichthe gateway receives email

(i.e., the relay domains) should be internal domains. By default all users and

domains are external.

Encryptmode (S & R) Encryptmode determines whetheramessagesent to

an external user (i.e., a user with external locality) should be encrypted or not.

The possible encrypt modes are: “No Encryption”, “Allow”, “Mandatory” and

“Allow (senderor recipient”. Encrypt modeis used for the sender andrecipient

(with the exception of Allow (sender or recipient)). If encrypt mode is “No en-

cryption”, the message will not be encrypted by default (unless being overruled

by the “subject trigger”). If mode is “Allow” the message is only encrypted if it

is possible to encrypt the message (i.e., a valid recipient certiﬁcate is available

or PDF encryptionis setup for therecipient). With “Mandatory”mode, the mes-

sage must be encrypted and if it is not possible to encrypt the message, the

message will not be sent and the sender will be notiﬁed.

Encrypt mode (except if the mode is Allow (sender or recipient))is a sender

and receiver preference. This means that the settings for both the sender and

receiver must allow encryption. If for example the sender has encrypt mode

“Mandatory” and the recipient has encrypt mode “No Encryption”, the message

will notbeencrypted and will thereforenotbesent (because thesender encrypt

mode was “Mandatory”). If the sender (or recipient) has encrypt mode “Allow

(sender or recipient)”, the other encrypt mode is ignored and encryption is

allowed. “Allow (sender or recipient)” encrypt mode is for example used when

all email sent to an external recipient should always be encrypted regardless

of the “Encrypt mode” of the sender.

Encryption notiﬁcation (S) If set, the sender of the message will be noti-

ﬁed (with an email) when the message is encrypted (see template “successful

encryption” on page50 for the notiﬁcation message template).

5.1.2 S/MIME

Enabled (S & R) If checked, digital signing and encryption of outgoing email

with S/MIME is supported.

Strictmode(R) Bydefault, thegatewaytriestodecrypteveryincomingS/MIME

encrypted message even if the recipient of the message does not have an as-

sociated private key withwhich themessagecanbedecrypted. Inother words,

the gateway tries to decrypt the message with any suitable key (“decrypt if

possible”). There are a couple of advantages when decrypting every incoming

email irrespective of the recipient: a) it makes it easier to manage domain to

If there isno “From” header, the “Sender” header will be used. If the “Sender”headerisalso

missing, the envelope senderwill be used.

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5.1 User preferences

5 USERS

domainencryption; b)forwarded email canbe decrypted and, c) email handling

with multiple recipients is faster because only one key is required for decryp-

tion.

Eventhoughnon-strict mode iseasier from amanagement perspective, it is

not as secure as “strict” mode. In non-strict mode, if an external attacker gets

hold of an encrypted message, the attacker can resend the message to an

internal accomplice, i.e., someone from inside the company who has access

to an internal mail box and who works closely with the attacker. Because the

message will decrypted with any available key, the message will be delivered

decrypted to the insider even though the insider was not the original recipient.

In “strict” mode, additional checks will be done to make sure that the message

will only bedecryptedif the recipient has avaliddecryptionkey. A messagewill

only be decryptedfor arecipientif the certiﬁcateassociated withthe private key

for decryption is valid, trusted, not revoked and if one of the following is true:

(a) the recipient has acertiﬁcate and privatekeywith amatchingemailaddress

and the message can be decrypted with this private key or,

(b) the recipient has a certiﬁcate and privatekey andthe certiﬁcate is explicitly

associated with the user and the message can be decrypted with the

private key or,

certiﬁcate and private key and the message can be decrypted with this

private key.

If in strict mode, every recipient for which none of the above rules apply, will

receive the message in encrypted form.

Whether or not to use strict mode depends mostly on whether you trust your

internal users. If you do not trust all internal users, it’s better to enable strict

mode. If all internal users can be trusted, running in non-strict mode might be

somewhat easier to manage.

Note: strict mode can be enabled and/or disabled per domain and per recip-

ient. Although it’s advised to only change the global strict settings, there are

situations where it can be helpful to enable ordisable strict mode per recipient.

For example, suppose the global strict mode is enabled. However, because

of email archiving purposes, the front-end SMTP server sends a copy (bcc)

of every incoming email to the email archiver. Since the gateway is in strict

mode, encrypted message won’t be decrypted by the gateway when delivered

to the email archiver. By disabling strict mode for the email archiver recipient,

incoming email delivered to the email archiver will be decrypted.

Max. message size (S | R) If the email message is larger than the speci-

ﬁed maximum messagesize (inbytes) the message will not be S/MIME signed

or encrypted. Large S/MIME messages can sometimes not be handled by

S/MIME email clients. Another reason for limiting the size of S/MIME mes-

sages is that encrypting and signing of large email messages can be resource

intensive.

5.1 User preferences

5 USERS

5.1.3 PGP

PGP enabled (S & R) If checked, PGP for outgoing email is supported.

PGP encoding to external (R) The PGP encoding used for outgoing email.

Two encodings are supported: PGP/MIME and PGP/INLINE. PGP/MIME isad-

vised because it secures the complete message MIME message and supports

HTML email. With PGP/INLINE, every MIME part is individually PGP encoded.

PGP/INLINE support forHTMLemail is limitedandis notsupported by all email

clients.

Note: YouarestronglyadvisedtousePGP/MIMEwheneverpossible.PGP/MIME

has full support for HTML email and is less resource intensive.

Enable PGP/INLINE to internal (R) PGP supports two types of encoding:

PGP/MIME and PGP/INLINE. With PGP/MIME, the complete MIME message

is protected as one object. A PGP/MIME protected message can be easily

recognized without having to scan the complete message because it contains

aPGP/MIME speciﬁc header. With PGP/INLINE, every individual part of the

message (attachments and message bodies) is individually protected (signed

and/or encrypted). To determine whether or not a message is PGP/INLINE

protected, the complete message must be scanned. A PGP/INLINE message

does not contain a speciﬁc header which can be used to determine whether

the message is PGP/INLINE protected. Scanning every incoming email com-

pletely from top to bottom can be resource intensive, especially for very large

attachments. It is therefore advised to leave “Incoming PGP/INLINE enabled”

unchecked (i.e., disabled) unless PGP/INLINE support for incoming email is a

requirement.

Note: leave“IncomingPGP/INLINEenabled”unchecked(i.e.,disabled)un-

less PGP/INLINE support for incoming email is a requirement.

Max. message size (S | R) If the email message is larger than the speciﬁed

maximum message size (in bytes) the message will not be PGP signed or

encrypted. LargePGP messagescansometimes notbehandledby PGP email

clients. Another reasonforlimiting thesizeof PGP messages is that encrypting

and signing of large email messages can be resource intensive.

5.1.4 PDF

Enabled (S & R) If checked, PDF encryption is supported.

OTP enabled (S & R) With the one time password mode, passwords for PDF

encryptionwill begeneratedbasedonthe“Client Secret” and on the“Password

ID”. For more information on the OTP mode, see the PDF encryption guide). If

selected, the one time password mode is enabled for the user.

5.1 User preferences

5 USERS

Generate password to originator (S & R) If checked, generated passwords

will be sent to the originator of the message (i.e., the sender) as a notiﬁcation

message. The notiﬁcation message will contain the generatedpasswords (see

template “passwords” on page50 for the notiﬁcation message template). The

originatoris responsiblefor delivering the generated passwords securely to the

recipients of the encrypted message.

Max. message size (S | R) PDF encryption not only encrypts the message

body but also encrypts the message attachments. To prevent the PDF from

becoming too large, the PDF is not encrypted if the total size of body text and

attachments exceeds the maximum message size (in bytes).

5.1.5 Password (R)

Password The password for the user. Currently this is only used for PDF

encryption. The password can be set by the administrator or can be randomly

generated. If the current password has expired (see “Validity interval”) a new

password will be generated when the password is used. If a static password

should be used, password expiration should be disabled by setting “Validity

interval” to -1.

Password ID (R) The “Password ID” identiﬁes the password used for PDF

encryption. The “Password ID” is required when the "One Time Password"

(OTP) mode is used or when the password is delivered by SMS Text.

With the OTP encryption mode, a password will be generated based on a

secret key andona unique identiﬁer (the “clientsecret”andthe“Password ID”).

The “Password ID” is used by the recipient of the encrypted PDF message to

regenerate the password (for more information about the OTP mode, see the

PDF encryption guide). With the SMS Text mode, the randomly generated

password will be delivered to the recipient via an SMS text message. Because

the recipient can receive multiple passwords via SMS Text, the recipient has

to know which password belongs to which encryptedPDF. The encrypted PDF

messages thereforecontaina passwordidentiﬁer which canbeusedto ﬁndthe

matching password. Every time a new password is generated, a new unique

password ID is generated. The “Password ID” property shows the last gener-

ated password ID for the user.

Validity interval (R) The time (in minutes) the password is valid. If the pass-

word is no longer valid (expired) a new password will be generated when the

password is used. If the “Validity interval” is 0 a new password will be gen-

erated every time a message is PDF encrypted. If “Validity interval” is -1 the

password never expires.

5.1.6 Encryption subject trigger

Asubject trigger can be used to force encryption if the subject contains a cer-

tain keyword. This is useful whenthedefault setting for a sender or recipient is

“No encryption” but the sender wants to force encryption of a particular mes-

sage (“on demand encryption”).

5.2 Advanced settings

5 USERS

Trigger (S) If the subject contains the provided trigger keyword and the sub-

ject trigger is enabled, encryption is forced for this message. Whether the

message is really encrypted depends on the availability of valid certiﬁcates for

the recipients. If encryption is triggered but the message cannot be encrypted,

the message will not be sent and the sender will be notiﬁed.

Enabled (S) The subject trigger functionality will only be functional if “En-

abled” is checked.

Regular expr. (S) If checked, “Trigger” is interpreted as a regular expression

and the subject is matched against this regular expression.

Example: (?i)(\[secure\]|\[encrypt\]).

With the above subject trigger, encryption will be forced if the subject contains

[secure] or [encrypt]. (?i) makes the check case insensitive.

Remove match (S) If checked, the matching part will be removed from the

subject.

Example: Suppose the trigger is set to "[encrypt]" and the subject of the in-

comingmessageis “your bank statement [encrypt]” thesubjectafterencryption

is “your bank statement”.

5.1.7 Signing

Only sign when encrypt (S & R) If checked, messages will only be digitally

signed when they are S/MIME or PGP encrypted. If not checked, all messages

will be digitallysigned. The sender of amessage musthave avalid signing cer-

tiﬁcate or PGP key before a message can be digitally signed. S/MIME signing

is tried before PGP signing, i.e., if a sender hasa validS/MIME signingkey, the

message will be S/MIME signed. If the sender does not have a valid S/MIME

signing key but has a valid PGP signing key, the message will be PGP signed.

5.2 Advanced settings

The advanced settings sub page contain settings which are only used in spe-

cialized setups (see ﬁgure19). Some settings can only be set for the global

settings. See5.3 for more information on the global speciﬁc settings.

5.2.1 General

Skip calendar messages (S | R) If checked, calendar messages4 (for ex-

ample Outlook meeting requests) are not digitally signed or encrypted. Some

email clients, for example Outlook, cannot handlemeetingrequestsif the meet-

ing requests are digitally signed or encrypted.

Messages with the content-type “text/calendar”

5.2 Advanced settings

5 USERS

Figure 19: Advanced user preferences

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