Understanding TLS Certificates and Connections

Understanding the TLS Protocol

The Transportation Layer Security protocol (TLS) is a widely-deployed method to protect and encrypt telecommunications. TLS protects many services, including web traffic, email, and many forms of Instant Messaging (IM). TLS elements may also vet degrees of hosts’ authenticity using chains-of-authority while processing communication of many forms. Mutually negotiable certificates are commonly exchanged promoting traceable trust between two hosts.

TLS operates at the Transport Layer (Layer 4) in the ISO/OSI stack. Other popular communications protection mechanisms operate at the Network Layer (IPSec) or the Application Layer (SSH) and even the Presentation Layer (SOCKS). TLS is a TCP-focused protocol, although variants use the Datagram TLS protocol ((D)TLS). This protocol works with out-of-order packet arrival or connections with high error rates and/or jitter. (D)TLS functionality almost completely mimes TLS, so the two can be considered synonymous for purposes of discussion.

TLS is operating system agnostic. The supported ciphers and certificate management characteristics of each host is usually a combination of the operating system, in combination with library and/or application resources used with the application and responding service. The applications, host operating systems, and libraries used with two hosts under TLS can be from completely different resources. Yet the connections achieves privacy, encryption, session management, and trust under TLS/(D)TLS.

The TLS Trust Relationship

The TLS trust relationship is established by one host evaluating an offer from another host. The host inspects a certificate for validity, perhaps against a stored reference certificate, a Certificate Authority (CA), or another desired trust fact (such as another factor of security seen in multi-factor authentication). The verification process uses weights against a trust score that must be met. Once the host accepts the trust score it proceeds to the next step, encryption selection and establishment. After that’s achieved, the hosts permit encrypted traffic.

The highest-denominator trust and strength of encryption are the most desirable ways to establish trust. It can be dangerous to use older cipher suites. However, some responding hosts may only negotiate a combination that is weaker, and hence more undesirable. Many modern browsers refuse to negotiate HTTPS with websites using older, more vulnerable cipher suite combinations.

Protocol Negotiation Methods and TLS Certificates

Protocol types have different negotiation methods. TLS for HTTPS web surfing is used differently than StartTLS used for mail exchange. Generally, you don’t see the construction and operational characteristics of TLS used unless an application alerts you about a stipulation problem. This can happen when there is a weak cipher request. In the case of email, for example, only the system administrator may see the generated error.

Most modern web browsers include a visual indication that TLS is working, such as a lock icon seen in the URL address bar. When the lock is in the lock position, often colored green, your connection is protected by TLS, as is the case when https works. The browser also indicates when the connection is not protected by TLS. When you click on the lock symbol, the browser shows the certificate and encryption relationship between the browser, its host, and the webserver to which it’s connected.

Traffic continues until the certificate expiration time occurs, or until there is an error indicating an alarm condition. Many conditions can trigger an alarm; only a few are considered cause for a recovery. Instead, a new TLS relationship is built between hosts to continue communications, if the conditions causing the error can be successfully removed.

The widest use of TLS trust is used on the Internet between web browsers and applications, and (web) servers. Browsers are provisioned with an initial store of certificate authorities, who are proxy parts of the certificate verification chain. When modern browsers encounter a certificate that is self-signed (self-authoritative), the browser sends you a warning.

Email and TLS

Email exchanges can be covered by TLS, and most are, but this is not a guarantee. Some SMTP hosts are simple, and do not have a TLS mechanism for exchanging mail. An SMTP host may use a TLS mechanism that supports weak trust methods or weak ciphers for mail exchange. Email servers supporting TLS aren’t held to as high a standard as web surfing, where HTTPS has become the mandated default communications privacy protocol.

TLS and Encryption

Encryption requires mathematical calculations to solve the formulas used to encrypt and decrypt TLS conversations. In the past, these calculations placed a high load on CPUs, and was often given as a reason against using TLS. Numerous CPU families now offer encryption/decryption optimizations which allow load capacity and scalability for server applications implementing TLS.

TLS Governance

TLS has been used for many years, and it is the successor to Secure Sockets Layer/SSL. The Internet Engineering Task Force’s IETF TLS Working Group is chartered with considering and evolving any changes. Each of the TLS Requests For Comments (RFCs) are published, building to the currently used RFC for TLS 1.3. Backwards compatibility with prior versions is necessary, although the reasons that prior versions of SSL and TLS were deprecated were because they had vulnerabilities with varying degrees of danger.

The Process of TLS Encryption and Trust

TLS connections are a multi-step process. Here’s how it works.

• An application initiates a TLS connection by connecting to a web server with HTTPS as a preamble rather than HTTP; TLS is intentional.
• The application and web server perform a handshake that initially encrypts the conversation.
• A negotiation begins regarding what cipher suites/encryption methods are to be used.
• Trust credentials are requested, exchanged, and once established, a session starts in full.

A Deeper Dive into TLS Connections and TLS Certificates

Initiating a Connection

To initiate a TLS link, a host application requests TLS coverage of another host. In web conversations, that’s accomplished by a browser making a URL request to a web server specifying the preamble URL of https. As the HTTPS protocol has become the default with many browsers, it has also become the default of many servers.

The https invocation specifically requests TLS/SSL (although SSL is usually discouraged) to the server. A server may accept an https address request call, and answer back with an https connection. If the browser cannot complete the TLS/https protocol, the server hangs up.

Once the initiating TLS transaction is done, a relationship between the two hosts occurs, as a stateful entity called a session. A series of messages constituting a handshake occurs between the hosts. This establishes message encryption, and therefore privacy. in TLS 1.3, a single request-and-answer then causes the next parts of the TLS protocol to be encrypted.

Next, the authenticity of the server’s credentials is checked. These are checked against either a local browser certificate cache or against a chain-of-authorities to a Certificate Authority. If all matches correctly, a session is established. It may have a stated maximum lifetime/expiration.

Once the TLS connection is made between the two hosts, it’s time to pick common encryption mechanisms/ciphers (and hopefully the highest common denominator between the two hosts). In the web service example, a browser has trust information presented by the web service. The browser looks to either its own cache of certificates, or to a chain-of-authorities statement made by the web server to prove its trust. If trust can be proven satisfactorily, and multiple options are possible, then a trust relationship is established (or rejected, ending the conversation).

Subsequent communications within the session is monitored by both hosts for out-of-normal conditions during exchanges. When the authentication method chosen expires or has an alarm condition, the communication session ends. Either host may tear down the session when it perceives that the session finishes, the session expires (the certificate is no longer valid or dies in other ways), or an alarm condition causes session termination.

The Life Cycle of a TLS Connection

1. A host makes a request to another host to begin a TLS conversation. This often uses an established IP address at a specific port (as ports represent application portals). Common ports are 443, 80, 8080.

2. The responding host replies to the requesting host, offering a choice of cipher or hash options.

3. The requesting host chooses a hash option offered, and then responds with a credentials request, now encrypted under the chosen option. Each side may have a minimum satisfactory option for a cipher and hash option set. The highest denominator between them is preferred, as older cipher options are sometimes vulnerable.

4. A series of communications between the hosts ensues. Among the offers-and-acceptance negotiation are the site’s credentials. The session ends if the requesting host refuses the credentials. This can occur for many reasons, but most commonly they’re refused because they’ve expired.

   If the credentials are not trusted, the destination host asks the requesting host if the stipulation it found is acceptable to the user. This might occur if, say, the responding host offers a self-signed certificate. Self-signed certificates require trust that cannot be verified by either the certificates stored locally (cached certificates, or using the chain of authorities stated in the credentials). A certificate authority is a third-party that could vet the proposed credentials. If it is unavailable, the proposition is implying that you have to trust the certificate without a means of vetting the credentials. That conundrum of trust is usually placed upon the user as an exception handling of trust responsibility. If the application using that requested TLS does not trust it, it forces you to accept this possibly-dubious trust in order to continue. In a browser request to a webserver under TLS, the browser stops cold, waiting for an acknowledgement by the user of this (and other) credential problems proposed by certificate exchange problems.

5. TLS sessions expire. Certificates propose a lifetime for which the site is trusted. The session expires automatically when the certificate does; a new session must be established, using a certificate that’s not expired. Some websites become suddenly and oddly available because their web administrators did not do the maintenance work of renewing an expired certificate.

Limitations

There may be other limitations, such as session activity timeouts. These may or may not be part of the TLS protocol. Whatever the reason, these timeouts end the session for the requester. Sessions may need to be renegotiated or re-authenticated, depending upon TLS protocols or (more often) policy limitations at the responding host.

A session may also terminate for other reasons unrelated to TLS. For example, the requesting host’s IP address might have changed; an MTU changed; or the requester is now using a different cipher or packet type. Any alarm condition that doesn’t have an administratively-managed remedy terminates a TLS session.

Ultimately, TLS is a multi-vendor, agnostic method of encrypting communications. It ensures trust in conversations between hosts, whether at the application level (as in web conversations) or as part of communications plumbing (email exchanges and more). Although older versions have proven to be vulnerable, more modern versions coupled with oversight by the IETF make TLS the widest choice in privacy and trust on the Internet.