S Mime

Honours Assignment 2
S/MIME
26/06/24
By Vijetha Y C
21CS1059
What is S/MIME?
S/MIME stands for Secure/Multipurpose Internet Mail Extensions,

and it is a standard that allows you to encrypt and sign your email
messages using public key cryptography. By using S/MIME, you
can ensure that your email messages are confidential, authentic,
and unmodified, regardless of who or where you send them to. It
protects your email messages from being hacked, tampered with,
or impersonated. It ensures the integrity of email messages
remains intact while being received.
By using digital signatures, S/MIME provides for authentication,

message integrity, and non-repudiation of origin. In addition,
S/MIME includes encryption that strengthens privacy and data
security for electronic messaging.
Before S/MIME
Emails could only be sent in NVT 7-bit format in the past, due to which
images, videos, or audio were not a part of e-mail attachments. Bell
Communications launched the MIME standard protocol in 1991 to increase
the email’s restricted functionality. S/MIME is an upgrade of
MIME(Multipurpose Internet Mail Extensions). Due to the limitations of
MIME, S/MIME came into play. S/MIME is based on asymmetric
cryptography which means that communications can be encrypted or
decrypted using a pair of related keys namely public and private keys.
How S/MIME Works
S/MIME is based on the principle of PKI, also called public key

cryptography, which uses two keys: a public key and a private
key. The public key is used to encrypt or lock the message, and
the private key is used to decrypt or unlock the message. The
public key can be shared with anyone, but the private key must be
kept secret by the owner.
S/MIME enables non-ASCII data to be sent using Secure Mail Transfer

Protocol (SMTP) via email. Moreover, many data files are sent, including
music, video, and image files. This data is securely sent using the encryption
method.
Via PKI, S/MIME utilizes digital certificates, which are digital

documents that contain the public key and other information about
the owner, such as the name, email address, and organization.
Certificates are issued and verified by trusted third parties, called
certificate authorities (CAs). Certificates help to establish the
trustworthiness and validity of the public keys and the identities of
the owners.
With a digital certificate, it can be applied as a digital signature on

emails as an extra level of security. It reassures the recipient that
the email was indeed signed by you, since you were verified by a
CA, and not a fraudster. The digital certificate acts as your
distinctive digital stamp, indicating to the recipient that the content
has remained unchanged during transmission. Any modifications
would render the signature invalid.
The process of digitally signing an email message with S/MIME is

as follows:
➔ After composing and before sending the message, enable

digital sign from your email client. This will create a hash
of the message.
➔ The private key will be used to encrypt the hash, and the
result will be the digital signature.
➔ The digital signature and the corresponding public key are
attached to the message when sent.
➔ The recipient can validate the sender from the public key.
And using the public key to verify the hash if it matches
with the content. This provides integrity of the message
and the identity of the sender.
* If the hash did not match, it means that the message has
been altered, and a corresponding note will appear.
The process of encrypting an email message with S/MIME is as

follows:
➔ The sender obtains the recipient’s public key, either by

exchanging digitally signed email or from a directory
service.
➔ The sender converts the message to ciphertext using a
symmetric algorithm. The symmetric algorithm is then
encrypted using the recipient’s public key.
➔ The ciphertext and the encrypted key are sent as a
package file, which can only be decrypted with the
recipient's private key using a supported email client.
➔ The recipient receives the package and verifies the
sender’s certificate and the digital signature, using the
sender’s public key and the same hash function. If the
verification is successful, it means that the message is
authentic and intact.
➔ The recipient decrypts the ciphertext with their own private
key, using the same symmetric encryption algorithm. The
decrypted message is called plaintext, and it is the original
message that the sender intended to send.
-- Alice (sender) generates a key pair and shares her public key
with Bob (a one-time prerequisite).
-- Alice signs the message using her private key in her device
and sends the message to Bob.
-- Bob receives the signed message on his device and verifies

the signature using Alice’s public key.
Why It’s Needed
In the early days of email, messages were transmitted in plain

text, which made them vulnerable to interception and tampering.
As the use of email for sensitive communications increased, the
need for a method to secure these messages became evident.
S/MIME was developed to provide a way to encrypt email
contents and to digitally sign messages, ensuring their
authenticity and integrity.
● S/MIME protects email communications via digital signature and

end-to-end encryption.
● Recipients can verify who you are and if someone tampered with
an email.
● Validation levels include email validation, individual validation,
and OV.
● Validation levels can affect what features are included with your
S/MIME certificate.
Purpose of S/MIME
The four primary purposes of S/MIME are:
➢ Confidentiality: Ensures that only the intended recipient can

read the email content.
➢ Authentication: Verifies the identity of the sender, ensuring
that the message is indeed from who it claims to be from.
➢ Integrity: Ensures that the message has not been altered
during transit.
➢ Non-repudiation: Prevents the sender from denying that they
sent the message.
A visual depiction of how S/MIME encryption works. The sender uses the recipient’s public key to
encrypt the message before sending the message to them to decrypt using their corresponding
private key.
Applications of S/MIME
❖ Email Encryption: Encrypts the contents of an email,

ensuring that only the intended recipient can decrypt and
read it.
❖ Digital Signatures: Signs the email with the sender's private
key, allowing the recipient to verify the sender's identity and
ensure that the message has not been altered.
❖ Secure Communication in Enterprises: Widely used in
corporate environments to secure internal communications
and ensure data privacy.
❖ Compliance: Helps organizations comply with regulatory
requirements for data protection and privacy, such as GDPR
and HIPAA.
Advantages of S/MIME
1. It offers verification.
2. It offers integrity to the message.
3. By the use of digital signatures, it facilitates non-repudiation of
origin.
4. It offers seclusion.
5. Data security is ensured by the utilization of encryption.
6. Transfer of data files like images, audio, videos, documents, etc. in a
secure manner.
New Techniques and Standards in Email Security After

S/MIME
Pretty Good Privacy (PGP)
PGP is another method for encrypting and signing email

messages. Unlike S/MIME, which relies on X.509 certificates
issued by trusted Certificate Authorities (CAs), PGP uses a
decentralized trust model called the Web of Trust.
Key Features:
● Decentralized Trust Model: Users create their own keys and

sign each other’s keys to build trust.
● End-to-End Encryption: Ensures that messages are
encrypted on the sender’s device and decrypted only on the
recipient’s device.
● Flexibility: Users can manage their own keys and decide
whom to trust.
Transport Layer Security (TLS)
TLS secures the transmission channel between email servers,

protecting emails in transit from being intercepted or tampered
with.
Key Features:
● Encryption in Transit: Protects data as it travels between

email servers.
● Server Authentication: Ensures that the server you are
communicating with is the one you intend to communicate
with.
● Widely Adopted: TLS is used not only for email but also for
securing web traffic and other forms of internet
communication.
Domain-based Message Authentication, Reporting &

Conformance (DMARC)
DMARC builds on SPF (Sender Policy Framework) and DKIM

(DomainKeys Identified Mail) to protect email domains from being
used for phishing and email spoofing.
Key Features:
● Email Authentication: Ensures that emails are sent from
legitimate sources.
● Reporting: Provides reports to domain owners about email
authentication failures.
● Policy Enforcement: Allows domain owners to specify how to
handle emails that fail authentication checks (e.g.,
quarantine or reject).
End-to-End Encrypted Email Services
Modern email services like ProtonMail and Tutanota offer built-in

end-to-end encryption, making secure email communication more
accessible to the average user.
Key Features:
● User-Friendly: Simplifies the process of sending and

receiving encrypted emails.
● Privacy-Focused: Often based in jurisdictions with strong
privacy laws.
● Additional Security Features: Includes features like zero-
access encryption and secure storage.
Conclusion
S/MIME protocol (or method) has been one of the safest ways to
transmit data or share data between companies or users. The
benefits that S/MIME provides are data integrity, confidentiality,
verification, and non-repudiation. Moreover, S/MIME has been
widely used for providing security services in various companies.

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Honours Assignment 2

S/MIME stands for Secure/Multipurpose Internet Mail Extensions,

By using digital signatures, S/MIME provides for authentication,

How S/MIME Works

S/MIME is based on the principle of PKI, also called public key

S/MIME enables non-ASCII data to be sent using Secure Mail Transfer

Via PKI, S/MIME utilizes digital certificates, which are digital

With a digital certificate, it can be applied as a digital signature on

The process of digitally signing an email message with S/MIME is

➔ After composing and before sending the message, enable

The process of encrypting an email message with S/MIME is as

➔ The sender obtains the recipient’s public key, either by

-- Bob receives the signed message on his device and verifies

Why It’s Needed

In the early days of email, messages were transmitted in plain

● S/MIME protects email communications via digital signature and

The four primary purposes of S/MIME are:

➢ Confidentiality: Ensures that only the intended recipient can

❖ Email Encryption: Encrypts the contents of an email,

3. By the use of digital signatures, it facilitates non-repudiation of

5. Data security is ensured by the utilization of encryption.

6. Transfer of data files like images, audio, videos, documents, etc. in a

New Techniques and Standards in Email Security After

Pretty Good Privacy (PGP)

PGP is another method for encrypting and signing email

● Decentralized Trust Model: Users create their own keys and

Transport Layer Security (TLS)

TLS secures the transmission channel between email servers,

● Encryption in Transit: Protects data as it travels between

Domain-based Message Authentication, Reporting &

DMARC builds on SPF (Sender Policy Framework) and DKIM

End-to-End Encrypted Email Services

Modern email services like ProtonMail and Tutanota offer built-in

● User-Friendly: Simplifies the process of sending and

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