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Mark,

On 7/14/16 4:14 PM, Mark Thomas wrote:
> On 14/07/2016 19:36, uzair rashid wrote:
>> Jeffrey,
>> 
>> Working for a corporation that has strict ssl and security
>> requirements.. There is no way to use the tools you suggested,
>> since the tomcat URLs are not exposed.
> 
> That doesn't stop you setting up a stand-alone test instance using
> the same settings (with a different cert if you are especially
> paranoid) and checking those settings using the excellent ssllabs.
> 
> Keeping your Tomcat and JVM versions up to date will also help.
> The Tomcat team periodically reviews Tomcat's default TLS
> configuration and adjusts it accordingly. For details of the most
> recent review see: https://wiki.apache.org/tomcat/Security/Ciphers

A few thoughts:

1. Since Tomcat can take OpenSSL-style cipher suites configuration, is
there a way to ask Tomcat to take an OpenSSL 'ciphers' specification
and have it emit the JSSE equivalent? I know Tomcat does this
internally, but can it dump the configuration for debugging purposes?

2. The OpenSSL ciphers specs on the "Ciphers" page above only includes
"HIGH" ciphers which is appropriate for today's safety, but it doesn't
prioritize them in any particular way. This may be the default for
OpenSSL, but I typically prioritize ECDHE and ECDH ciphers before the
other ones in the HIGH category.

3. There's usually no reason to include the "PSK" (pre-shared key)
ciphers in your server's cipher spec, so I always disable those as well.

4. It's fairly important to enable "server-order" cipher suite
selection, so that the server's preferences are used over the client's
preferences, in case you have a lay client who would choose a trivial
cipher if it were available. This is, for example, how older versions
of MSIE behave: they REALLY prefer to use cipher suites using RC4 even
if higher-grade ones are available. Of course, you should really
disable cipher suites you aren't willing to use, but sometimes you
just HAVE to include some really bad ciphers in the list in order to
support super-old clients.

5. Many people don't know about the "Unlimited Strength Policy Files".
I've been thinking that we might want to issue an INFO message at
startup if TLS/JSSE is in use and the "Unlimited Strength Policy
Files" aren't available. This may encourage more people to install
them. Unfortunately, I don't know if a way to install those files
without modifying the JRE being used to launch the JVM. If anyone
knows how they can be installed just for one application (Tomcat), it
would be nice to provide a guide for how to do that.

6. Qualys has a tool called ssllabs-scan available on GitHub:
https://github.com/ssllabs/ssllabs-scan/

I haven't read-through the code yet, but I suspect it's a copy of the
whole scanner and doesn't "phone home" (except maybe to grab the
latest configuration and scoring rules). This may make it possible to
scan some of those internal servers that aren't facing the public
Internet (and therefore can't be scanned directly using ssllabs
web-based tool). It may also speed-up the scanning of a site, since
their web-based tool is throttled to avoid using it as a DOS tool.

The existence of the ssllabs-scan tool means it's also possible to
set-up automated periodic scanning of your own site(s). If you expect
to get an "A" rating and one day you aren't "A" quality any more, you
should get an alarm without having to remember to manually-run the
web-based tool when you get around to doing it.

Have fun. Be safe.

- -chris
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