Testing for SSL-TLS (OWASP-CM-001)

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Brief Summary

Due to historical exporting restrictions of high grade cryptography, legacy and new web servers could be able to handle a weak cryptographic support.

Even if high grade ciphers are normally used and installed, some misconfiguration in server installation could be used to force the use of a weaker cipher to gain access to the supposed secure communication channel.

Testing SSL / TLS cipher specifications and requirements for site

The http clear-text protocol is normally secured via an SSL or TLS tunnel, resulting in https traffic. In addition to providing encryption of data in transit, https allows the identification of servers (and, optionally, of clients) by means of digital certificates.

Historically, there have been limitations set in place by the U.S. government to allow cryptosystems to be exported only for key sizes of, at most, 40 bits, a key length which could be broken and would allow the decryption of communications. Since then, cryptographic export regulations have been relaxed (though some constraints still hold); however, it is important to check the SSL configuration being used to avoid putting in place cryptographic support which could be easily defeated. SSL-based services should not offer the possibility to choose weak ciphers.

Technically, cipher determination is performed as follows. In the initial phase of a SSL connection setup, the client sends to the server a Client Hello message specifying, among other information, the cipher suites that it is able to handle. A client is usually a web browser (most popular SSL client nowadays…), but not necessarily, since it can be any SSL-enabled application; the same holds for the server, which needs not be a web server, though this is the most common case. (For example, a noteworthy class of SSL clients is that of SSL proxies such as stunnel (www.stunnel.org) which can be used to allow non-SSL enabled tools to talk to SSL services.) A cipher suite is specified by an encryption protocol (DES, RC4, AES), the encryption key length (such as 40, 56, or 128 bits), and a hash algorithm (SHA, MD5) used for integrity checking. Upon receiving a Client Hello message, the server decides which cipher suite it will use for that session. It is possible (for example, by means of configuration directives) to specify which cipher suites the server will honour. In this way you may control, for example, whether or not conversations with clients will support 40-bit encryption only.

Black Box Test and example

In order to detect possible support of weak ciphers, the ports associated to SSL/TLS wrapped services must be identified. These typically include port 443, which is the standard https port; however, this may change because a) https services may be configured to run on non-standard ports, and b) there may be additional SSL/TLS wrapped services related to the web application. In general, a service discovery is required to identify such ports.

The nmap scanner, via the “–sV” scan option, is able to identify SSL services. Vulnerability Scanners, in addition to performing service discovery, may include checks against weak ciphers (for example, the Nessus scanner has the capability of checking SSL services on arbitrary ports, and will report weak ciphers).

Example 1. SSL service recognition via nmap.

[root@test]# nmap -F -sV localhost

Starting nmap 3.75 ( http://www.insecure.org/nmap/ ) at 2005-07-27 14:41 CEST
Interesting ports on localhost.localdomain (
(The 1205 ports scanned but not shown below are in state: closed)

443/tcp   open  ssl             OpenSSL
901/tcp   open  http            Samba SWAT administration server
8080/tcp  open  http            Apache httpd 2.0.54 ((Unix) mod_ssl/2.0.54 OpenSSL/0.9.7g PHP/4.3.11)
8081/tcp  open  http            Apache Tomcat/Coyote JSP engine 1.0

Nmap run completed -- 1 IP address (1 host up) scanned in 27.881 seconds

Example 2. Identifying weak ciphers with Nessus. The following is an anonymized excerpt of a report generated by the Nessus scanner, corresponding to the identification of a server certificate allowing weak ciphers (see underlined text).

 https (443/tcp)
 Here is the SSLv2 server certificate:
 Version: 3 (0x2)
 Serial Number: 1 (0x1)
 Signature Algorithm: md5WithRSAEncryption
 Issuer: C=**, ST=******, L=******, O=******, OU=******, CN=******
 Not Before: Oct 17 07:12:16 2002 GMT
 Not After : Oct 16 07:12:16 2004 GMT
 Subject: C=**, ST=******, L=******, O=******, CN=******
 Subject Public Key Info:
 Public Key Algorithm: rsaEncryption
 RSA Public Key: (1024 bit)
 Modulus (1024 bit):
 Exponent: 65537 (0x10001)
 X509v3 extensions:
 X509v3 Basic Constraints:
 Netscape Comment:
 OpenSSL Generated Certificate
 Page 10
 Network Vulnerability Assessment Report 25.05.2005
 X509v3 Subject Key Identifier:
 X509v3 Authority Key Identifier:
 Signature Algorithm: md5WithRSAEncryption
 Here is the list of available SSLv2 ciphers:
 The SSLv2 server offers 5 strong ciphers, but also 0 medium strength and 2 weak "export class" ciphers.
 The weak/medium ciphers may be chosen by an export-grade or badly configured client software. They only offer a limited protection against a brute force attack
 Solution: disable those ciphers and upgrade your client software if necessary.
 See http://support.microsoft.com/default.aspx?scid=kben-us216482
 or http://httpd.apache.org/docs-2.0/mod/mod_ssl.html#sslciphersuite
 This SSLv2 server also accepts SSLv3 connections.
 This SSLv2 server also accepts TLSv1 connections.
 Vulnerable hosts
 (list of vulnerable hosts follows)

Example 3. Manually audit weak SSL cipher levels with OpenSSL. The following will attempt to connect to Google.com with SSLv2.

[root@test]# openssl s_client -no_tls1 -no_ssl3 -connect www.google.com:443
depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=www.google.com
verify error:num=20:unable to get local issuer certificate
verify return:1
depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=www.google.com
verify error:num=27:certificate not trusted
verify return:1
depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=www.google.com
verify error:num=21:unable to verify the first certificate
verify return:1
Server certificate
subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=www.google.com
issuer=/C=ZA/ST=Western Cape/L=Cape Town/O=Thawte Consulting cc/OU=Certification Services Division/CN=Thawte Premium Server CA/emailAddress=premium-server@thawte.com
No client certificate CA names sent
Ciphers common between both SSL endpoints:
RC4-MD5         EXP-RC4-MD5     RC2-CBC-MD5
SSL handshake has read 1023 bytes and written 333 bytes
New, SSLv2, Cipher is DES-CBC3-MD5
Server public key is 1024 bit
Compression: NONE
Expansion: NONE
    Protocol  : SSLv2
    Cipher    : DES-CBC3-MD5
    Session-ID: 709F48E4D567C70A2E49886E4C697CDE
    Master-Key: 649E68F8CF936E69642286AC40A80F433602E3C36FD288C3
    Key-Arg   : E8CB6FEB9ECF3033
    Start Time: 1156977226
    Timeout   : 300 (sec)
    Verify return code: 21 (unable to verify the first certificate)

White Box Test and example

Check the configuration of the web servers which provide https services. If the web application provides other SSL/TLS wrapped services, these should be checked as well.

Example: The registry path in windows 2k3 defines the ciphers available to the server:


Testing SSL certificate validity – client and server

When accessing a web application via the https protocol, a secure channel is established between the client (usually the browser) and the server. The identity of one (the server) or both parties (client and server) is then established by means of digital certificates. In order for the communication to be set up, a number of checks on the certificates must be passed. While discussing SSL and certificate based authentication is beyond the scope of this Guide, we will focus on the main criteria involved in ascertaining certificate validity: a) checking if the Certificate Authority (CA) is a known one (meaning one considered trusted), b) checking that the certificate is currently valid, and c) checking that the name of the site and the name reported in the certificate match. Remember to upgrade your browser because CA certs expired too, in every release of the browser, CA Certs has been renews. Moreover it's important to update the browser because more web sites require strong cipher more of 40 or 56 bit.

Let’s examine each check more in detail.

a) Each browser comes with a preloaded list of trusted CAs, against which the certificate signing CA is compared (this list can be customized and expanded at will). During the initial negotiations with a https server, if the server certificate relates to a CA unknown to the browser, a warning is usually raised. This happens most often because a web application relies on a certificate signed by a self-established CA. Whether this is to be considered a concern depends on several factors. For example, this may be fine for an Intranet environment (think of corporate web email being provided via https; here, obviously all users recognize the internal CA as a trusted CA). When a service is provided to the general public via the Internet, however (i.e. when it is important to positively verify the identity of the server we are talking to), it is usually imperative to rely on a trusted CA, one which is recognized by all the user base (and here we stop with our considerations, we won’t delve deeper in the implications of the trust model being used by digital certificates).

b) Certificates have an associated period of validity, therefore they may expire. Again, we are warned by the browser about this. A public service needs a temporally valid certificate; otherwise, it means we are talking with a server whose certificate was issued by someone we trust, but has expired without being renewed.

c) What if the name on the certificate and the name of the server do not match? If this happens, it might sound suspicious. For a number of reasons, this is not so rare to see. A system may host a number of name-based virtual hosts, which share the same IP address and are identified by means of the HTTP 1.1 Host: header information. In this case, since the SSL handshake checks the server certificate before the HTTP request is processed, it is not possible to assign different certificates to each virtual server. Therefore, if the name of the site and the name reported in the certificate do not match, we have a condition which is typically signalled by the browser. To avoid this, IP-based virtual servers must be used. [2] and [3] describe techniques to deal with this problem and allow name-based virtual hosts to be correctly referenced.

Black Box Testing and examples

Examine the validity of the certificates used by the application. Browsers will issue a warning when encountering expired certificates, certificates issued by untrusted CAs, and certificates which do not match namewise with the site jto which they should refer. By clicking on the padlock which appears in the browser window when visiting an https site, you can look at information related to the certificate – including the issuer, period of validity, encryption characteristics, etc.

If the application requires a client certificate, you probably have installed one to access it. Certificate information is available in the browser by inspecting the relevant certificate(s) in the list of the installed certificates.

These checks must be applied to all visible SSL-wrapped communication channels used by the application. Though this is the usual https service running on port 443, there may be additional services involved depending on the web application architecture and on deployment issues (an https administrative port left open, https services on non-standard ports, etc.). Therefore, apply these checks to all SSL-wrapped ports which have been discovered. For example, the nmap scanner features a scanning mode (enabled by the –sV command line switch) which identifies SSL-wrapped services. The Nessus vulnerability scanner has the capability of performing SSL checks on all SSL/TLS-wrapped services.


Rather than providing a fictitious example, we have inserted an anonymized real-life example to stress how frequently one stumbles on https sites whose certificates are inaccurate with respect to naming.

The following screenshots refer to a regional site of a high-profile IT company.

Warning issued by Microsoft Internet Explorer. We are visiting a .it site and the certificate was issued to a .com site! Internet Explorer warns that the name on the certificate does not match the name of the site.

SSL Certificate Validity Testing IE Warning.gif

Warning issued by Mozilla Firefox. The message issued by Firefox is different – Firefox complains because it cannot ascertain the identity of the .com site the certificate refers to because it does not know the CA which signed the certificate. In fact, Internet Explorer and Firefox do not come preloaded with the same list of CAs. Therefore, the behavior experienced with various browsers may differ.

SSL Certificate Validity Testing Firefox Warning.gif

White Box Testing and examples

Examine the validity of the certificates used by the application at both server and client levels. The usage of certificates is primarily at the web server level; however, there may be additional communication paths protected by SSL (for example, towards the DBMS). You should check the application architecture to identify all SSL protected channels.




  • Vulnerability scanners may include checks regarding certificate validity, including name mismatch and time expiration. They usually report other information as well, such as the CA which issued the certificate. Remember that there is no unified notion of a “trusted CA”; what is trusted depends on the configuration of the software and on the human assumptions made beforehand. Browsers come with a preloaded list of trusted CAs. If your web application relies on a CA which is not in this list (for example, because you rely on a self-made CA), you should take into account the process of configuring user browsers to recognize the CA.
  • The Nessus scanner includes a plugin to check for expired certificates or certificates which are going to expire within 60 days (plugin “SSL certificate expiry”, plugin id 15901). This plugin will check certificates installed on the server.
  • Vulnerability scanners may include checks against weak ciphers. For example, the Nessus scanner (http://www.nessus.org) has this capability and flags the presence of SSL weak ciphers (see example provided above).
  • You may also rely on specialized tools such as SSL Digger (http://www.foundstone.com/resources/proddesc/ssldigger.htm), or – for the command line oriented – experiment with the openssl tool, which provides access to OpenSSL cryptographic functions directly from a Unix shell (may be already available on *nix boxes, otherwise see www.openssl.org).
  • To identify SSL-based services, use a vulnerability scanner or a port scanner with service recognition capabilities. The nmap scanner features a “-sV” scanning option which tries to identify services, while the nessus vulnerability scanner has the capability of identifying SSL-based services on arbitrary ports and to run vulnerability checks on them regardless of whether they are configured on standard or non-standard ports.
  • In case you need to talk to a SSL service but your favourite tool doesn’t support SSL, you may benefit from a SSL proxy such as stunnel; stunnel will take care of tunneling the underlying protocol (usually http, but not necessarily so) and communicate with the SSL service you need to reach.
  • Finally, a word of advice. Though it may be tempting to use a regular browser to check certificates, there are various reasons for not doing so. Browsers have been plagued by various bugs in this area, and the way the browser will perform the check might be influenced by configuration settings that may not be evident. Instead, rely on vulnerability scanners or on specialized tools to do the job.

OWASP Testing Guide v2

Here is the OWASP Testing Guide v2 Table of Contents