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RedHat 6.2 Apache 2.2.15

I've installed a new SSL certificate on my apache server and updated the /etc/httpd/conf.d/ssl.conf file to include the new details:

#   Server Certificate:
# Point SSLCertificateFile at a PEM encoded certificate.  If
# the certificate is encrypted, then you will be prompted for a
# pass phrase.  Note that a kill -HUP will prompt again.  A new
# certificate can be generated using the genkey(1) command.
SSLCertificateFile /etc/httpd/ssl/2016/pathtocert.crt

#   Server Private Key:
#   If the key is not combined with the certificate, use this
#   directive to point at the key file.  Keep in mind that if
#   you've both a RSA and a DSA private key you can configure
#   both in parallel (to also allow the use of DSA ciphers, etc.)
SSLCertificateKeyFile /etc/httpd/ssl/2016/pathtokey.key

#   Certificate Authority (CA):
#   Set the CA certificate verification path where to find CA
#   certificates for client authentication or alternatively one
#   huge file containing all of them (file must be PEM encoded)
SSLCACertificateFile /etc/httpd/ssl/2016/bundle.crt

After restarting httpd and visiting the website it is still using the old certificate which expires in a few weeks. (I also tested by running the domain through https://www.digicert.com)

I confirmed that it is defintely using that ssl.conf file, by removing it and then the server failed to load. And then confirmed that it was defintely loading those files, by changing to an incorrect path and the server again failed to load.

I ran the following from the terminal:

openssl s_client -connect domainhere.co.uk:443 -showcerts

And it showed the correct certificates (QuoVadis)

I also tried it using the IP address of the server and again it returned the correct certificates.

So then I tried using the external IP address and that is where it was returning the old certificates (TERENA), so that is where the problem lies.

So I know what the issue is, but I'm not sure how to fix that.

There is nothing about SSL in my httpd.conf file, but there are virtual hosts and NameVirtualHosts for http on the internal IP address.

All the SSL configuration is in the ssl.conf file, where the virtualhost uses the domain name instead of either IP address:

Listen 443
(...)
<VirtualHost mydomain.co.uk:443>
#   SSL Engine Switch:
#   Enable/Disable SSL for this virtual host.
SSLEngine on

#   SSL Protocol support:
# List the enable protocol levels with which clients will be able to
# connect.  Disable SSLv2 access by default:
SSLProtocol all -SSLv2

#   SSL Cipher Suite:
# List the ciphers that the client is permitted to negotiate.
# See the mod_ssl documentation for a complete list.
SSLCipherSuite ALL:!ADH:!EXPORT:!SSLv2:RC4+RSA:+HIGH:+MEDIUM:+LOW

#   Server Certificate:
# Point SSLCertificateFile at a PEM encoded certificate.  If
# the certificate is encrypted, then you will be prompted for a
# pass phrase.  Note that a kill -HUP will prompt again.  A new
# certificate can be generated using the genkey(1) command.
SSLCertificateFile /etc/httpd/ssl/2016/pathtocert.crt

#   Server Private Key:
#   If the key is not combined with the certificate, use this
#   directive to point at the key file.  Keep in mind that if
#   you've both a RSA and a DSA private key you can configure
#   both in parallel (to also allow the use of DSA ciphers, etc.)
SSLCertificateKeyFile /etc/httpd/ssl/2016/pathto.key

#   Server Certificate Chain:
#   Point SSLCertificateChainFile at a file containing the
#   concatenation of PEM encoded CA certificates which form the
#   certificate chain for the server certificate. Alternatively
#   the referenced file can be the same as SSLCertificateFile
#   when the CA certificates are directly appended to the server
#   certificate for convinience.
#SSLCertificateChainFile /etc/httpd/ssl/2016/bundle.crt

#   Certificate Authority (CA):
#   Set the CA certificate verification path where to find CA
#   certificates for client authentication or alternatively one
#   huge file containing all of them (file must be PEM encoded)
SSLCACertificateFile /etc/httpd/ssl/2016/bundle.crt

#   Client Authentication (Type):
#   Client certificate verification type and depth.  Types are
#   none, optional, require and optional_no_ca.  Depth is a
#   number which specifies how deeply to verify the certificate
#   issuer chain before deciding the certificate is not valid.
#SSLVerifyClient require
#SSLVerifyDepth  10

#   Access Control:
#   With SSLRequire you can do per-directory access control based
#   on arbitrary complex boolean expressions containing server
#   variable checks and other lookup directives.  The syntax is a
#   mixture between C and Perl.  See the mod_ssl documentation
#   for more details.
#<Location />
#SSLRequire (    %{SSL_CIPHER} !~ m/^(EXP|NULL)/ \
#            and %{SSL_CLIENT_S_DN_O} eq "Snake Oil, Ltd." \
#            and %{SSL_CLIENT_S_DN_OU} in {"Staff", "CA", "Dev"} \
#            and %{TIME_WDAY} >= 1 and %{TIME_WDAY} <= 5 \
#            and %{TIME_HOUR} >= 8 and %{TIME_HOUR} <= 20       ) \
#           or %{REMOTE_ADDR} =~ m/^192\.76\.162\.[0-9]+$/
#</Location>

#   SSL Engine Options:
#   Set various options for the SSL engine.
#   o FakeBasicAuth:
#     Translate the client X.509 into a Basic Authorisation.  This means that
#     the standard Auth/DBMAuth methods can be used for access control.  The
#     user name is the `one line' version of the client's X.509 certificate.
#     Note that no password is obtained from the user. Every entry in the user
#     file needs this password: `xxj31ZMTZzkVA'.
#   o ExportCertData:
#     This exports two additional environment variables: SSL_CLIENT_CERT and
#     SSL_SERVER_CERT. These contain the PEM-encoded certificates of the
#     server (always existing) and the client (only existing when client
#     authentication is used). This can be used to import the certificates
#     into CGI scripts.
#   o StdEnvVars:
#     This exports the standard SSL/TLS related `SSL_*' environment variables.
#     Per default this exportation is switched off for performance reasons,
#     because the extraction step is an expensive operation and is usually
#     useless for serving static content. So one usually enables the
#     exportation for CGI and SSI requests only.
#   o StrictRequire:
#     This denies access when "SSLRequireSSL" or "SSLRequire" applied even
#     under a "Satisfy any" situation, i.e. when it applies access is denied
#     and no other module can change it.
#   o OptRenegotiate:
#     This enables optimized SSL connection renegotiation handling when SSL
#     directives are used in per-directory context. 
#SSLOptions +FakeBasicAuth +ExportCertData +StrictRequire
<Files ~ "\.(cgi|shtml|phtml|php3?)$">
    SSLOptions +StdEnvVars
</Files>
<Directory "/var/www/cgi-bin">
    SSLOptions +StdEnvVars
</Directory>

#   SSL Protocol Adjustments:
#   The safe and default but still SSL/TLS standard compliant shutdown
#   approach is that mod_ssl sends the close notify alert but doesn't wait for
#   the close notify alert from client. When you need a different shutdown
#   approach you can use one of the following variables:
#   o ssl-unclean-shutdown:
#     This forces an unclean shutdown when the connection is closed, i.e. no
#     SSL close notify alert is send or allowed to received.  This violates
#     the SSL/TLS standard but is needed for some brain-dead browsers. Use
#     this when you receive I/O errors because of the standard approach where
#     mod_ssl sends the close notify alert.
#   o ssl-accurate-shutdown:
#     This forces an accurate shutdown when the connection is closed, i.e. a
#     SSL close notify alert is send and mod_ssl waits for the close notify
#     alert of the client. This is 100% SSL/TLS standard compliant, but in
#     practice often causes hanging connections with brain-dead browsers. Use
#     this only for browsers where you know that their SSL implementation
#     works correctly. 
#   Notice: Most problems of broken clients are also related to the HTTP
#   keep-alive facility, so you usually additionally want to disable
#   keep-alive for those clients, too. Use variable "nokeepalive" for this.
#   Similarly, one has to force some clients to use HTTP/1.0 to workaround
#   their broken HTTP/1.1 implementation. Use variables "downgrade-1.0" and
#   "force-response-1.0" for this.
SetEnvIf User-Agent ".*MSIE.*" \
         nokeepalive ssl-unclean-shutdown \
         downgrade-1.0 force-response-1.0

#   Per-Server Logging:
#   The home of a custom SSL log file. Use this when you want a
#   compact non-error SSL logfile on a virtual host basis.
CustomLog logs/ssl_request_log \
          "%t %h %{SSL_PROTOCOL}x %{SSL_CIPHER}x \"%r\" %b"

</VirtualHost>

Could anyone advise me what I need to change in the configuration so that accessing through the external IP address loads the new certificates?

Thanks.

  • 1
    Do you have anything in front of apache like an nginx proxy or something? They could still be retaining the old certs. – daemonofchaos Dec 6 '16 at 16:51
  • Just out of curiosity have you cleared your browser cache or tried a different browser. The certificate is checked against the domain name, not the ip. – Anthony Fornito Dec 6 '16 at 16:53
  • @DaemonofChaos, not as far as I can see. I ran lsof -i :443 -S and the only thing coming up is a few httpd processes. – CMR Dec 6 '16 at 16:57
  • @AnthonyFornito Yeah I tried that. I'm also running the check through that digicert website though, which wouldn't have that problem. (It picked up the new certificates on another server of ours instantly) – CMR Dec 6 '16 at 16:58
  • 1
    Working internally and not externally, I agree with DaemonofChaos that there might be something in front of the web server that is caching the old SSL. Maybe run a tracert from the webserver to the gateway and see how many hops it take. – Anthony Fornito Dec 6 '16 at 17:19
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Turns out there was a TMG instance running on that network, which was sending its own SSL certificates for the server.

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