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There are 4 easy ways to check that SSLv2 and weak ciphers are disabled on your web servers and appliances. SSLv2 is deprecated and should never be used. You will definitely need to verify these are disabled for PCI compliance and SOX compliance. The instructions below apply to check SSLv2 on any web server (IIS, Apache, iPlanet, etc.) or any traffic or load balancing appliance (Citrix Netscaler, F5 BigIP, etc.).

1. SSLDigger - Download it here http://www.foundstone.com/us/resources/proddesc/ssldigger.htm. It’s a great little tool that first tests for SSLv2, then gives you the option to test for weak ciphers one by one, then spits our a nice little HTML report of the findings. You can even create a .txt file with all your URLs to test and perform testing in bulk. This is wonderful when you have many domains to test and need to give a report to management quickly.

Checking the Google.com SSL cert (click to enlarge):

Checking for weak ciphers systematically (click to enlarge):

HTML report (click to enlarge):

2. OpenSSL – The old favorite. Type the following to connect to your web server or appliance over SSLv2:

openssl s_client -connect www.yourdomain.com:443 -ssl2

It should connect giving you a CONNECTED(000007C0) message but then immediately fail and display an error message like one of the following:

419:error:1407F0E5:SSL routines:SSL2_WRITE:ssl handshake failure:s2_pkt.c:428:
420:error:1406D0B8:SSL routines:GET_SERVER_HELLO:no cipher list:s2_clnt.c:450:
10076:error:1407F0E5:SSL routines:SSL2_WRITE:ssl handshake failure:. \ssl\s2_pkt.c:428:
write:errno=548965:error:1407F0E5:SSL routines:SSL2_WRITE:ssl handshake failure:s2_pkt.c:428:
write:errno=10054

SSL handshake failures and connection resets (errno=10054) are completely normal if SSLv2 is disabled. The specific error message you get will depend on exactly what behavior your web server or appliance is configured to do when a client connects using it.

Example of SSLv2 disabled:

Example of SSLv2 enabled (VERY VERY BAD!):

3. Nessus – Download it here http://www.nessus.org and use the Home Feed and setup a new scan using the SSL Anonymous Cipher Suites Supported and SSL Version 2 (v2) Protocol Detection plugins. Please make sure to disable all the other plugins, you don’t want all that hitting your server. Just these 2 are sufficient. Then check the Reports and see if it is reporting SSLv2 as a vulnerability.

4. External SSL checkers – Running nice little tools like the above three is nice to check your servers when you are internal but if you want to see what 3rd parties are seeing externally, use one of these online SSL checkers to test:

http://foundeo.com/products/iis-weak-ssl-ciphers/test.cfm
http://www.dnsstuff.com/tools/

You can use OpenSSL and run this command:

openssl.exe s_client -connect www.mysite.com:443

which will use a generic SSL/TLS client to connect to your site and give you a ton of diagnostic info.  You can see your entire SSL cert chain, the SSL handshake, SSL session info, etc.  Here’s a full list of switches you can use with it:  http://www.openssl.org/docs/apps/s_client.html

And here’s a great online tool to graphically verify your SSL chain is intact:  http://www.sslshopper.com/ssl-checker.html

Often times you might have to add an SSL cert to a Cisco or Citrix appliance (like a Netscaler) but it only accepts the SSL cert and private key in a certain format.  Your CA (certificate authority) will issue the SSL cert to you as a .crt.  From there, you need to package the cert with the private key and in the format your appliance requires.  There are different ways to do this and one easy way I like is using IIS and OpenSSL which is a free open source tool and can be downloaded here:  http://www.openssl.org

1. Create a temporary site in IIS and generate a CSR.  Make sure the CN (common name) you enter matches whatever appliance you are trying to generate it for exmp:  wireless.mycompany.com

2.  Submit the CSR to your CA such as Verisign, GoDaddy, Network Solutions, etc. and wait for them to validate and issue your cert.

3. Get the .crt from the CA once they issue it and convert it to .cer.  Just open the .crt by double clicking on it and and save it as .cer using the export wizard.  This is necessary since IIS does not accept .crt.

4. Install the .cer in IIS using the Web Server Certificate Wizard where you originally generated the CSR.  Just process the pending request to install it.

5. View the cert in IIS and export it with the private key in pkcs12 (.pfx) format.  Just set the password as “password” since you will be deleting it after conversion is complete later.

6. Go to the directory where OpenSSL.exe is and type in the following to convert the .pfx to a .pem

openssl pkcs12 -in nameofcert.pfx -out nameofcert.pem

7. Type the “password” when prompted for the pass phrase.

8. Install the .pem on the appliance and it should work

IMPORTANT NOTE:

If you are doing it for some appliances like a Cisco IronPort, you need to add the nodes switch when creating the .pem:

openssl pkcs12 -in nameofcert.pfx -out nameofcert.pem –nodes

The –nodes switch ensures that the key inside the .pem is left unencrypted.  If you attempt to install a .pem created without the -nodes switch, the appliance will take the cert but will not accept the private key since it cannot read it in an encrypted state.