Help getting SSL security installed on Ubuntu 16.04

February 4, 2017 333 views
Configuration Management Ubuntu 16.04

Hi all, for 3-4 years I had a domain SSL-secured on my server running Ubuntu 14.04. Recently I wiped it and started with a fresh install of Ubuntu 16.04. If I use 000-default.conf and simply have it do HTTP on port 80 there are no problems; but when I try configuring default-ssl.conf with the SSL certificates I got from GoDaddy and my private key file, no joy whatsoever. I've talked to several IT experts about my problem, but no one seems to be able to help me out. Anyone ever have a similar problem in 16.04. Nothing very exciting in terms of error logs. At least not that I can see. Again, we are talking about a system that worked fine in 14.04 with SSL; only when I moved in a fresh install to 16.04 did it stop working. Yes, I chose a2ensite, did a2enmod SSL, restarted apache2, am sure port 443 is opened in UFW, etc. But no go. Anyone been here and done this?

4 Answers


An SSL Certificate generated on one host (i.e. VPS) won't work on another. You'd need to generate a CSR (Certificate Signing Request) as you did when you first setup the certificate and then go through the reissue process with your certificate provider.

So what you need to do is start by generating a CSR for your certificate from the CLI.

openssl req -new -newkey rsa:2048 -nodes -keyout domainname.key -out domainname.csr

To get the output of the CSR:

cat domainname.csr

The CSR would then be provided to your provider to reissue your SSL Certificate.

Once you have your certificate, you would then modify your web server config to use the new certificate files, or overwrite the existing, and restart the web server.

I did generate the .csr and related .key file, inserted it in my rekey request from my certificate provider, got back a zip with two .crt files in it, that I put into a .../ssl/certs directory and put my privatekey.key file in the ..../ssl/private directory. Used default-ssl.conf and enabled module with a2enmod ssl, restarted apache2, I even tried fiddling with 000-default.conf in sites-available, since I have no problem with that, thinking I could also include the VirtualHost *:443 directive along with the VirtualHost *:80 that does work fine. Really a puzzle. Thanks for your help with this. If you or anyone else happens to have an idea what is going wrong, please contact me. Again, I had SSL working just fine on same OS (but version 14.04) and same server for several years. But when I wiped it and reinstalled a fresh install of 16.04, only HTTP works. Not SSL on same domain.


If you've already reissued the certificate, then we'd need to take a look at your configuration files for the domain in question. If you're not having issues with accessing your domain on port 80, then we'll skip that file and take a look at the VirtualHost block that handles port 443.

If you can copy and paste that in to a code block as a reply, I'll be more than happy to take a look. If needed, you can change the domain name if you prefer not to post that -- just use or any other filler.

many thanks for your willingness to take a look at my issue. this is my slightly doctored default-ssl.conf file. again, 000-default.conf works just fine. but when I try loading this one with a2ensite, followed by a2enmod ssl and a reboot of apache2, I can no longer get to my domain.

Unless I am putting in the wrong files here it should work. When I sent my CSR file to get back the 2 .crt files I chose Apache server from the list, that included IIS, Tomcat, etc. So it must be right, too. Again, I had 0 problems with this in Ubuntu 14.04; only after wiping my server and reinstalling fresh version of 16.04 did the mystery begin. Here goes:

<IfModule mod_ssl.c>
<VirtualHost _default_:443>
DocumentRoot /var/www/html

            # Available loglevels: trace8, ..., trace1, debug, info, notice, warn,
            # error, crit, alert, emerg.
            # It is also possible to configure the loglevel for particular
            # modules, e.g.
            #LogLevel info ssl:warn

            ErrorLog ${APACHE_LOG_DIR}/error.log
            CustomLog ${APACHE_LOG_DIR}/access.log combined

            # For most configuration files from conf-available/, which are
            # enabled or disabled at a global level, it is possible to
            # include a line for only one particular virtual host. For example the
            # following line enables the CGI configuration for this host only
            # after it has been globally disabled with "a2disconf".
            #Include conf-available/serve-cgi-bin.conf

            #   SSL Engine Switch:
            #   Enable/Disable SSL for this virtual host.
            SSLEngine on

            #   A self-signed (snakeoil) certificate can be created by installing
            #   the ssl-cert package. See
            #   /usr/share/doc/apache2/README.Debian.gz for more info.
            #   If both key and certificate are stored in the same file, only the
            #   SSLCertificateFile directive is needed.
    SSLCertificateFile      /etc/ssl/certs/mycertificatefile.crt
            SSLCertificateKeyFile /etc/ssl/private/myprivatekey.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/ssl/certs/mybundle.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)
            #   Note: Inside SSLCACertificatePath you need hash symlinks
            #                to point to the certificate files. Use the provided
            #                Makefile to update the hash symlinks after changes.
            #SSLCACertificatePath /etc/ssl/certs/
            #SSLCACertificateFile /etc/ssl/certs/

            #   Certificate Revocation Lists (CRL):
            #   Set the CA revocation path where to find CA CRLs for client
            #   authentication or alternatively one huge file containing all
            #   of them (file must be PEM encoded)
            #   Note: Inside SSLCARevocationPath you need hash symlinks
            #                to point to the certificate files. Use the provided
            #                Makefile to update the hash symlinks after changes.
            #SSLCARevocationPath /etc/apache2/ssl.crl/
            #SSLCARevocationFile /etc/apache2/ssl.crl/ca-bundle.crl
    #   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

            #   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 OptRenegotiate:
            #        This enables optimized SSL connection renegotiation handling when SSL
            #        directives are used in per-directory context.
            #SSLOptions +FakeBasicAuth +ExportCertData +StrictRequire
    <FilesMatch "\.(cgi|shtml|phtml|php)$">
                            SSLOptions +StdEnvVars
            <Directory /usr/lib/cgi-bin>
                            SSLOptions +StdEnvVars

            #   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.
            # BrowserMatch "MSIE [2-6]" \
    #               nokeepalive ssl-unclean-shutdown \
            #               downgrade-1.0 force-response-1.0



vim: syntax=apache ts=4 sw=4 sts=4 sr noet
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