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S/MIME (Secure/Multipurpose internet Mail Extensions) is a widely accepted protocol for sending digitally signed and encrypted messages. S/MIME in Exchange Online provides the following services for email messages:

Encryption: Protects the content of email messages.
Digital signatures: Verifies the identity of the sender of an email message.

The rest of this article generally describes S/MIME and how these services work.

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To configure S/MIME in Exchange Online, see the following topics:

S/MIME digital signatures

Digital signatures are the more commonly used service of S/MIME. As the name suggests, digital signatures are the digital counterpart to the traditional, legal signature on a paper document. As with a legal signature, digital signatures provide the following security capabilities:

Authentication: A signature serves to validate an identity. It verifies the answer to 'who are you' by providing a means of differentiating that entity from all others and proving its uniqueness. Because there is no authentication in SMTP email, there is no way to know who sent a message. Authentication in a digital signature solves this problem by allowing a recipient to know that a message was sent by the person or organization who claims to have sent the message.
Nonrepudiation: The uniqueness of a signature prevents the owner of the signature from disowning the signature. This capability is called nonrepudiation. Thus, the authentication that a signature provides gives the means to enforce nonrepudiation. The concept of nonrepudiation is most familiar in the context of paper contracts: a signed contract is a legally binding document, and it is impossible to disown an authenticated signature. Digital signatures provide the same function and, increasingly in some areas, are recognized as legally binding, similar to a signature on paper. Because SMTP email does not provide a means of authentication, it cannot provide nonrepudiation. It is easy for a sender to disavow ownership of an SMTP email message.
Data integrity: An additional security service that digital signatures provide is data integrity. Data integrity is a result of the specific operations that make digital signatures possible. With data integrity services, when the recipient of a digitally signed email message validates the digital signature, the recipient is assured that the email message that is received is, in fact, the same message that was signed and sent, and has not been altered while in transit. Any alteration of the message while in transit after it has been signed invalidates the signature. In this way, digital signatures provide an assurance that signatures on paper cannot, because it is possible for a paper document to be altered after it has been signed.

Important

Although digital signatures provide data integrity, they don't provide confidentiality. Messages with only a digital signature are sent in clear text, like SMTP messages and can be read by others. In the case where the message is opaque-signed, a level of obfuscation is achieved because the message is base64-encoded, but it is still clear text. To protect the contents of email messages, encryption must be used.

S/MIME encryption

Message encryption provides a solution to information disclosure. SMTP-based internet email does not secure messages. An SMTP internet email message can be read by anyone who sees it as it travels or views it where it is stored. These problems are addressed by S/MIME using encryption. Encryption is a way to change information so that it cannot be read or understood until it is changed back into a readable and understandable form. Message encryption provides two specific security services:

Confidentiality: Message encryption serves to protect the contents of an email message. Only the intended recipient can view the contents, and the contents remain confidential and cannot be known by anyone else who might receive or view the message. Encryption provides confidentiality while the message is in transit and in storage.
Dataintegrity: As with digital signatures, message encryption provides data integrity services as a result of the specific operations that make encryption possible.

Important

Although message encryption provides confidentiality, it doesn't authenticate the message sender in any way. An unsigned, encrypted message is as susceptible to sender impersonation as a message that isn't encrypted. Because nonrepudiation is a direct result of authentication, message encryption also doesn't provide nonrepudiation. Although encryption does provide data integrity, an encrypted message can show only that the message hasn't been altered since it was sent. No information about who sent the message is provided. To prove the identity of the sender, the message must use a digital signature.

Related message encryption technologies

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Other encryption technologies work together to provide protection for messages at rest and in-transit. S/MIME can work simultaneously with the technologies in the following list, but is not dependent on them:

Transport Layer Security (TLS) which replaces Secure Sockets Layer (SSL):
- Encrypts the tunnel or the route between email servers in order to help prevent snooping and eavesdropping.
- Encrypts the connection between email clients and email servers.
BitLocker: Encrypts data on hard drives in client computers and servers. If an unauthorized party somehow gains access, they can't read the data on the drives.

Office 365 Message Encryption is a direct competitor to S/MIME, and has the following advantages over S/MIME:

It's a policy-based encryption service that's configured by an admin to encrypt messages that are sent to anyone inside or outside of the organization. In contrast, users are required to decide whether to apply or not apply S/MIME to messages that they send.
It's an online service that's built on Azure Rights Management (Azure RMS) and does not rely on a public key infrastructure. In contrast, S/MIME requires a certificate and certificate publishing infrastructure.
Office 365 Message Encryption provides additional capabilities. For example, you can customize messages with your organization's brand.

Dec 26, 2020 Solution 11-2: Install the S/MIME from the options section in your OWA client (see #5 above). If you have problems installing the S/MIME check to make sure that 'Do not save encrypted pages to disk' is unchecked under Tools, Advanced (tab). NOTE: The S/MIME will ONLY work with the 32 bit version of Internet Explorer. It is not compatible with.
Secure Email Reader will delete the file from your mobile device after successfully importing the key material. Next time you see an smime.p7m or smime.p7s attachment in Mail or in your web mail client, just open it using Secure Email Reader. You’ll be able to decrypt it and access any attachments. Secure Email Reader for Android.
Solution 11-2: Install the S/MIME from the options section in your OWA client (see #5 above). If you have problems installing the S/MIME check to make sure that 'Do not save encrypted pages to disk' is unchecked under Tools, Advanced (tab). NOTE: The S/MIME will ONLY work with the 32 bit version of Internet Explorer. It is not compatible with.
S/MIME (Secure/Multipurpose Internet Mail Extensions) is a widely accepted method (or more precisely, a protocol) for sending digitally signed and encrypted messages. S/MIME allows you to encrypt emails and digitally sign them. When you use S/MIME with an email message, it helps the people who.

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I understand that you want to use S/MIME to access encrypted emails on Microsoft Web Outlook. I’ll certainly help you with the issue. Ideally, the first step to use S/MIME is to obtain a certificate from your IT administrator or helpdesk. You can also refer the article Encrypt messages by using S/MIME in Outlook on the web and see if that helps.

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S/MIME (Secure/Multipurpose Internet Mail Extensions) is a standard for public keyencryption and signing of MIME data. S/MIME is on an IETFstandards track and defined in a number of documents, most importantly RFC3369, 3370, 3850 and 3851. It was originally developed by RSA Data Security and the original specification used the IETF MIME specification^[1] with the de facto industry standard PKCS#7 secure message format. Change control to S/MIME has since been vested in the IETF and the specification is now layered on Cryptographic Message Syntax (CMS), an IETF specification that is identical in most respects with PKCS #7. S/MIME functionality is built into the majority of modern email software and interoperates between them. Since it is built on CMS, MIME can also hold an advanced electronic signature.

Function[edit]

S/MIME provides the following cryptographic security services for electronic messaging applications:

Message integrity
Non-repudiation of origin (using digital signatures)
Privacy
Data security (using encryption)

S/MIME specifies the MIME type application/pkcs7-mime^[2] (smime-type 'enveloped-data') for data enveloping (encrypting) where the whole (prepared) MIME entity to be enveloped is encrypted and packed into an object which subsequently is inserted into an application/pkcs7-mime MIME entity.

S/MIME certificates[edit]

Before S/MIME can be used in any of the above applications, one must obtain and install an individual key/certificate either from one's in-house certificate authority (CA) or from a public CA. The accepted best practice is to use separate private keys (and associated certificates) for signature and for encryption, as this permits escrow of the encryption key without compromise to the non-repudiation property of the signature key. Encryption requires having the destination party's certificate on store (which is typically automatic upon receiving a message from the party with a valid signing certificate). While it is technically possible to send a message encrypted (using the destination party certificate) without having one's own certificate to digitally sign, in practice, the S/MIME clients will require the user to install their own certificate before they allow encrypting to others. This is necessary so the message can be encrypted for both, recipient and sender, and a copy of the message can be kept (in the sent folder) and be readable for the sender.

A typical basic ('class 1') personal certificate verifies the owner's 'identity' only insofar as it declares that the sender is the owner of the 'From:' email address in the sense that the sender can receive email sent to that address, and so merely proves that an email received really did come from the 'From:' address given. It does not verify the person's name or business name. If a sender wishes to enable email recipients to verify the sender's identity in the sense that a received certificate name carries the sender's name or an organization's name, the sender needs to obtain a certificate ('class 2') from a CA who carries out a more in-depth identity verification process, and this involves making inquiries about the would-be certificate holder. For more detail on authentication, see digital signature.

Depending on the policy of the CA, the certificate and all its contents may be posted publicly for reference and verification. This makes the name and email address available for all to see and possibly search for. Other CAs only post serial numbers and revocation status, which does not include any of the personal information. The latter, at a minimum, is mandatory to uphold the integrity of the public key infrastructure.

S/MIME Working Group of CA/Browser Forum[edit]

In 2020, the S/MIME Certificate Working Group^[3] of the CA/Browser Forum was chartered to create a baseline requirement applicable to CAs that issue S/MIME certificates used to sign, verify, encrypt, and decrypt email. That effort is intended to created standards including:

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Certificate profiles for S/MIME certificates and CAs that issue them
Verification of control over email addresses
Identity validation
Key management, certificate lifecycle, CA operational practices, etc.

Obstacles to deploying S/MIME in practice[edit]

S/MIME is sometimes considered not properly suited for use via webmail clients. Though support can be hacked into a browser, some security practices require the private key to be kept accessible to the user but inaccessible from the webmail server, complicating the key advantage of webmail: providing ubiquitous accessibility. This issue is not fully specific to S/MIME: other secure methods of signing webmail may also require a browser to execute code to produce the signature; exceptions are PGP Desktop and versions of GnuPG, which will grab the data out of the webmail, sign it by means of a clipboard, and put the signed data back into the webmail page. Seen from the view of security this is a more secure solution.
S/MIME is tailored for end-to-end security. Logically it is not possible to have a third party inspecting email for malware and also have secure end-to-end communications. Encryption will not only encrypt the messages, but also the malware. Thus if mail is not scanned for malware anywhere but at the end points, such as a company's gateway, encryption will defeat the detector and successfully deliver the malware. The only solution to this is to perform malware scanning on end user stations after decryption. Other solutions do not provide end-to-end trust as they require keys to be shared by a third party for the purpose of detecting malware. Examples of this type of compromise are:
- Solutions which store private keys on the gateway server so decryption can occur prior to the gateway malware scan. These unencrypted messages are then delivered to end users.
- Solutions which store private keys on malware scanners so that it can inspect messages content, the encrypted message is then relayed to its destination.
Due to the requirement of a certificate for implementation, not all users can take advantage of S/MIME, as some may wish to encrypt a message, with a public/private key pair for example, without the involvement or administrative overhead of certificates.

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Any message that an S/MIME email client stores encrypted cannot be decrypted if the applicable key pair's private key is unavailable or otherwise unusable (e.g., the certificate has been deleted or lost or the private key's password has been forgotten). However, an expired, revoked, or untrusted certificate will remain usable for cryptographic purposes. Indexing of encrypted messages' clear text may not be possible with all email clients. Neither of these potential dilemmas is specific to S/MIME but rather cipher text in general and do not apply to S/MIME messages that are only signed and not encrypted.

S/MIME signatures are usually 'detached signatures': the signature information is separate from the text being signed. The MIME type for this is multipart/signed with the second part having a MIME subtype of application/(x-)pkcs7-signature. Mailing list software is notorious for changing the textual part of a message and thereby invalidating the signature; however, this problem is not specific to S/MIME, and a digital signature only reveals that the signed content has been changed.

Security issues[edit]

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On May 13, 2018, the Electronic Frontier Foundation (EFF) announced critical vulnerabilities in S/MIME, together with an obsolete form of PGP that is still used, in many email clients.^[4] Dubbed EFAIL, the bug required significant coordinated effort by many email client vendors to fix.^[5]

References[edit]

^RFC 2045: Multipurpose Internet Mail Extensions (MIME). Part One was published in November 1996.
^Balladelli, Micky; Clercq, Jan De (2001). Mission-critical Active Directory: Architecting a Secure and Scalable Infrastructure for Windows 2000. p. 550. ISBN9781555582401. S/MIME adds new MIME content types that provide data confidentiality, integrity protection, nonrepudiation, and authentication services: application/pkcs7-mime, multipart/signed, and application/pkcs7-signature
^ CA/Browser Forum S/MIME Certificate Working Group https://cabforum.org/working-groups/smime-certificate-wg/
^Gebhart, Danny O'Brien and Gennie (2018-05-13). 'Attention PGP Users: New Vulnerabilities Require You To Take Action Now'. Electronic Frontier Foundation. Retrieved 2018-05-29.
^Hansen, Robert (2018-05-20). 'Efail: A Postmortem'. Robert Hansen. Retrieved 2018-05-30.

External links[edit]

RFC 5652: Cryptographic Message Syntax (CMS)
RFC 3370: Cryptographic Message Syntax (CMS) Algorithms
RFC 5751: Secure/Multipurpose Internet Mail Extensions (S/MIME) Version 3.2 Message Specification
RFC 8551: Secure/Multipurpose Internet Mail Extensions (S/MIME) Version 4.0 Message Specification
Microsoft Exchange Server: Understanding S/MIME (high-level overview).

Retrieved from 'https://en.wikipedia.org/w/index.php?title=S/MIME&oldid=1000674009'

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