SSLCertificateFile: file '/private/etc/apache2/server.crt' does not exist or is empty

Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g., so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.

My domain is:

I ran this command: sudo certbot --apache

It produced this output:
Saving debug log to /var/log/letsencrypt/letsencrypt.log
Error while running apachectl configtest.
AH00526: Syntax error on line 144 of /private/etc/apache2/extra/httpd-ssl.conf:
SSLCertificateFile: file ‘/private/etc/apache2/server.crt’ does not exist or is empty
The apache plugin is not working; there may be problems with your existing configuration.
The error was: MisconfigurationError(“Error while running apachectl configtest.\n\nAH00526: Syntax error on line 144 of /private/etc/apache2/extra/httpd-ssl.conf:\nSSLCertificateFile: file ‘/private/etc/apache2/server.crt’ does not exist or is empty\n”)

My web server is (include version): Apache/2.4.34 (Unix)

The operating system my web server runs on is (include version): Mac OS Mojave

My hosting provider, if applicable, is: ME and my macmini

I can login to a root shell on my machine (yes or no, or I don’t know):I don’t know

I’m using a control panel to manage my site (no, or provide the name and version of the control panel): no

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you’re using Certbot): 0.32.0

MY NOTES: I am a total newbie, having setup apache on mac, finally got localhost/virtual host [*.80] configured, a whole day spent understanding/editing “httpd.conf”
“httpd-vhosts.conf” - tldr - did have a “hello world” page showing under http

SO all my research for SSL Cert use LetsEncrypt

Installed Homebrew, certbot
Ran certbot --apache [automated]
HOWEVER after getting - Unable to install the certificate I then discovered some modifications to httpd.conf regarding SSL were not dome prior

I AM CURRENTLY in a hole - HELP NEEDED as I do not know how to fix this

In hind site the certbot --apache SHOULD of either alerted to this OR corrected/halted proceedings

SO with…
Error while running apachectl configtest.
AH00526: Syntax error on line 144 of /private/etc/apache2/extra/httpd-ssl.conf:
SSLCertificateFile: file ‘/private/etc/apache2/server.crt’ does not exist or is empty

IS THERE a fix

thank you

PS have since edit the httpd.conf regarding SSL “unhashing” and has made no difference

Hi @coldes

share the content of that file.

Start with ``` (three accent grave), then a new row, then the file content, a new row and three accent grave again.

# This is the Apache server configuration file providing SSL support.
# It contains the configuration directives to instruct the server how to
# serve pages over an https connection. For detailed information about these 
# directives see <URL:>
# Do NOT simply read the instructions in here without understanding
# what they do.  They're here only as hints or reminders.  If you are unsure
# consult the online docs. You have been warned.  
# Required modules: mod_log_config, mod_setenvif, mod_ssl,
#          socache_shmcb_module (for default value of SSLSessionCache)

# Pseudo Random Number Generator (PRNG):
# Configure one or more sources to seed the PRNG of the SSL library.
# The seed data should be of good random quality.
# WARNING! On some platforms /dev/random blocks if not enough entropy
# is available. This means you then cannot use the /dev/random device
# because it would lead to very long connection times (as long as
# it requires to make more entropy available). But usually those
# platforms additionally provide a /dev/urandom device which doesn't
# block. So, if available, use this one instead. Read the mod_ssl User
# Manual for more details.
#SSLRandomSeed startup file:/dev/random  512
#SSLRandomSeed startup file:/dev/urandom 512
#SSLRandomSeed connect file:/dev/random  512
#SSLRandomSeed connect file:/dev/urandom 512

# When we also provide SSL we have to listen to the 
# standard HTTP port (see above) and to the HTTPS port
Listen 443

##  SSL Global Context
##  All SSL configuration in this context applies both to
##  the main server and all SSL-enabled virtual hosts.

#   SSL Cipher Suite:
#   List the ciphers that the client is permitted to negotiate,
#   and that httpd will negotiate as the client of a proxied server.
#   See the OpenSSL documentation for a complete list of ciphers, and
#   ensure these follow appropriate best practices for this deployment.
#   httpd 2.2.30, 2.4.13 and later force-disable aNULL, eNULL and EXP ciphers,
#   while OpenSSL disabled these by default in 0.9.8zf/1.0.0r/1.0.1m/1.0.2a.
SSLProxyCipherSuite HIGH:MEDIUM:!MD5:!RC4:!3DES

#  By the end of 2016, only TLSv1.2 ciphers should remain in use.
#  Older ciphers should be disallowed as soon as possible, while the
#  kRSA ciphers do not offer forward secrecy.  These changes inhibit
#  older clients (such as IE6 SP2 or IE8 on Windows XP, or other legacy
#  non-browser tooling) from successfully connecting.  
#  To restrict mod_ssl to use only TLSv1.2 ciphers, and disable
#  those protocols which do not support forward secrecy, replace
#  the SSLCipherSuite and SSLProxyCipherSuite directives above with
#  the following two directives, as soon as practical.
# SSLProxyCipherSuite HIGH:MEDIUM:!SSLv3:!kRSA

#   User agents such as web browsers are not configured for the user's
#   own preference of either security or performance, therefore this
#   must be the prerogative of the web server administrator who manages
#   cpu load versus confidentiality, so enforce the server's cipher order.
SSLHonorCipherOrder on 

#   SSL Protocol support:
#   List the protocol versions which clients are allowed to connect with.
#   Disable SSLv3 by default (cf. RFC 7525 3.1.1).  TLSv1 (1.0) should be
#   disabled as quickly as practical.  By the end of 2016, only the TLSv1.2
#   protocol or later should remain in use.
SSLProtocol all -SSLv3
SSLProxyProtocol all -SSLv3

#   Pass Phrase Dialog:
#   Configure the pass phrase gathering process.
#   The filtering dialog program (`builtin' is an internal
#   terminal dialog) has to provide the pass phrase on stdout.
SSLPassPhraseDialog  builtin

#   Inter-Process Session Cache:
#   Configure the SSL Session Cache: First the mechanism 
#   to use and second the expiring timeout (in seconds).
#SSLSessionCache         "dbm:/private/var/run/ssl_scache"
SSLSessionCache        "shmcb:/private/var/run/ssl_scache(512000)"
SSLSessionCacheTimeout  300

#   OCSP Stapling (requires OpenSSL 0.9.8h or later)
#   This feature is disabled by default and requires at least
#   the two directives SSLUseStapling and SSLStaplingCache.
#   Refer to the documentation on OCSP Stapling in the SSL/TLS
#   How-To for more information.
#   Enable stapling for all SSL-enabled servers:
#SSLUseStapling On

#   Define a relatively small cache for OCSP Stapling using
#   the same mechanism that is used for the SSL session cache
#   above.  If stapling is used with more than a few certificates,
#   the size may need to be increased.  (AH01929 will be logged.)
#SSLStaplingCache "shmcb:/private/var/run/ssl_stapling(32768)"

#   Seconds before valid OCSP responses are expired from the cache
#SSLStaplingStandardCacheTimeout 3600

#   Seconds before invalid OCSP responses are expired from the cache
#SSLStaplingErrorCacheTimeout 600

## SSL Virtual Host Context

<VirtualHost _default_:443>

#   General setup for the virtual host
DocumentRoot "/Library/WebServer/Documents"
ErrorLog "/private/var/log/apache2/error_log"
TransferLog "/private/var/log/apache2/access_log"

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

#   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.  Keep
#   in mind that if you have both an RSA and a DSA certificate you
#   can configure both in parallel (to also allow the use of DSA
#   ciphers, etc.)
#   Some ECC cipher suites (
#   require an ECC certificate which can also be configured in
#   parallel.
SSLCertificateFile "/private/etc/apache2/server.crt"
#SSLCertificateFile "/private/etc/apache2/server-dsa.crt"
#SSLCertificateFile "/private/etc/apache2/server-ecc.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.)
#   ECC keys, when in use, can also be configured in parallel
SSLCertificateKeyFile "/private/etc/apache2/server.key"
#SSLCertificateKeyFile "/private/etc/apache2/server-dsa.key"
#SSLCertificateKeyFile "/private/etc/apache2/server-ecc.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 convenience.
#SSLCertificateChainFile "/private/etc/apache2/server-ca.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 "/private/etc/apache2/ssl.crt"
#SSLCACertificateFile "/private/etc/apache2/ssl.crt/ca-bundle.crt"

#   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).
#   The CRL checking mode needs to be configured explicitly
#   through SSLCARevocationCheck (defaults to "none" otherwise).
#   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 "/private/etc/apache2/ssl.crl"
#SSLCARevocationFile "/private/etc/apache2/ssl.crl/ca-bundle.crl"
#SSLCARevocationCheck chain

#   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

#   TLS-SRP mutual authentication:
#   Enable TLS-SRP and set the path to the OpenSSL SRP verifier
#   file (containing login information for SRP user accounts). 
#   Requires OpenSSL 1.0.1 or newer. See the mod_ssl FAQ for
#   detailed instructions on creating this file. Example:
#   "openssl srp -srpvfile /private/etc/apache2/passwd.srpv -add username"
#SSLSRPVerifierFile "/private/etc/apache2/passwd.srpv"

#   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]+$/

#   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
<FilesMatch "\.(cgi|shtml|phtml|php)$">
    SSLOptions +StdEnvVars
<Directory "/Library/WebServer/CGI-Executables">
    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 sent or allowed to be 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 [2-5]" \
         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 "/private/var/log/apache2/ssl_request_log" \
          "%t %h %{SSL_PROTOCOL}x %{SSL_CIPHER}x \"%r\" %b"


Row 144

SSLCertificateFile "/private/etc/apache2/server.crt"

Does that file exist? If not, add a # as first char in that row.

…ok added #, now the following

Damiens-Mac-mini:~ cdplMacMini$ sudo apachectl configtest
AH00526: Syntax error on line 154 of /private/etc/apache2/extra/httpd-ssl.conf:
SSLCertificateKeyFile: file '/private/etc/apache2/server.key' does not exist or is empty

therefore # the start of line 154?

Same problem - if you use files, they have to exist.

…ok, added a hash to line 154 [remember I am BRAND NEW to all of this - all I did was follow install prompts from cerbot website, expecting all of this to be taken care off]
apache config Syntax OK
however I have not setup

<VirtualHost *:443>

Do I do this OR is this created by certbot install? re-install?

If I have to which file do I edit and exactly with what info? I am confused because if I have no server.crt or server.key how can I have SSL.
Now the current test “hello world” page can’t be reached

I really appreciate your prompt assistance with all of this, however treat me as a 6 yr old
BTW, if Apple had correctly got their ssl cert/chain AND not dropped support I would not be here at almost 10pm - ie am setting up web hosting on a new mac… thanks

1 Like

If your port 80 vHost is correct, certbot creates the port 443 vHost with the new values.

PS: You have already a certificate:

So try to reinstall that:

certbot -d -d --reinstall

yes port 80 vhost is set and was fully working before ssl mod / edits
will now try the reinstall…

The following error was encountered:
[Errno 13] Permission denied: '/var/log/letsencrypt/.certbot.lock'
Either run as root, or set --config-dir, --work-dir, and --logs-dir to writeable paths.


is your answer.

?? how [now a guess - should reinstall code line you gave me have started with sudo?] - remember 6 yrs old… and one full day in mac Terminal [just a dumb designer]

Yes, sudo is your friend.

1 Like

…note error line 9 lines down

Saving debug log to /var/log/letsencrypt/letsencrypt.log
Plugins selected: Authenticator apache, Installer apache
Cert not yet due for renewal
Keeping the existing certificate
Created an SSL vhost at /private/etc/apache2/extra/httpd-vhosts-le-ssl.conf
Deploying Certificate to VirtualHost /private/etc/apache2/extra/httpd-vhosts-le-ssl.conf
Enabling site /private/etc/apache2/extra/httpd-vhosts-le-ssl.conf by adding Include to root configuration
Deploying Certificate to VirtualHost /private/etc/apache2/extra/httpd-vhosts-le-ssl.conf
Error while running apachectl configtest.

AH00526: Syntax error on line 13 of /etc/letsencrypt/options-ssl-apache.conf:
Setting Compression mode unsupported; not implemented by the SSL library

Rolling back to previous server configuration...
Error while running apachectl configtest.

AH00526: Syntax error on line 13 of /etc/letsencrypt/options-ssl-apache.conf:
Setting Compression mode unsupported; not implemented by the SSL library

 - We were unable to install your certificate, however, we
   successfully restored your server to its prior configuration.
 - Congratulations! Your certificate and chain have been saved at:
   Your key file has been saved at:
   Your cert will expire on 2019-06-18. To obtain a new or tweaked
   version of this certificate in the future, simply run certbot again
   with the "certonly" option. To non-interactively renew *all* of
   your certificates, run "certbot renew"
 - Some rewrite rules copied from
   /private/etc/apache2/extra/httpd-vhosts.conf were disabled in the
   vhost for your HTTPS site located at
   /private/etc/apache2/extra/httpd-vhosts-le-ssl.conf because they
   have the potential to create redirection loops.

What's the content of that file / row? Perhaps remove that row.

[apologies for response delay, power outage!] …full contents of file “options-ssl-apache.conf”

# This file contains important security parameters. If you modify this file
# manually, Certbot will be unable to automatically provide future security
# updates. Instead, Certbot will print and log an error message with a path to
# the up-to-date file that you will need to refer to when manually updating
# this file.

SSLEngine on

# Intermediate configuration, tweak to your needs
SSLProtocol             all -SSLv2 -SSLv3
SSLHonorCipherOrder     on
SSLCompression          off

SSLOptions +StrictRequire

# Add vhost name to log entries:
LogFormat "%h %l %u %t \"%r\" %>s %b \"%{Referer}i\" \"%{User-agent}i\"" vhost_combined
LogFormat "%v %h %l %u %t \"%r\" %>s %b" vhost_common

#CustomLog /var/log/apache2/access.log vhost_combined
#LogLevel warn
#ErrorLog /var/log/apache2/error.log

# Always ensure Cookies have "Secure" set (JAH 2012/1)
#Header edit Set-Cookie (?i)^(.*)(;\s*secure)??((\s*;)?(.*)) "$1; Secure$3$4"

…took a punt, added # start line 13, then ran reinstall

- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
Congratulations! You have successfully enabled and

You should test your configuration at:
- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -

HOWEVER no connection to website!?! NOW I am at LOSS…
A summary…

<VirtualHost *:80>
ServerName localhost
DocumentRoot /Library/WebServer/Documents/

<VirtualHost *:80>
    DocumentRoot "/Users/cdplMacMini/Sites/"
    ErrorLog "/private/var/log/apache2/"
    CustomLog "/private/var/log/apache2/" common
RewriteEngine on
RewriteCond %{SERVER_NAME} [OR]
RewriteCond %{SERVER_NAME}
RewriteRule ^ https://%{SERVER_NAME}%{REQUEST_URI} [END,NE,R=permanent]


<IfModule mod_ssl.c>
<VirtualHost *:443>
    DocumentRoot "/Users/cdplMacMini/Sites/"
    ErrorLog "/private/var/log/apache2/"
    CustomLog "/private/var/log/apache2/" common

   RewriteEngine on
# Some rewrite rules in this file were disabled on your HTTPS site,
# because they have the potential to create redirection loops.

#    RewriteCond %{SERVER_NAME}
#    RewriteRule ^ https://%{SERVER_NAME}%{REQUEST_URI} [END,QSA,R=permanent]

Include /etc/letsencrypt/options-ssl-apache.conf
SSLCertificateFile /etc/letsencrypt/live/
SSLCertificateKeyFile /etc/letsencrypt/live/

Where to from here?..

Your domain ( )

Domainname Http-Status redirect Sec. G -2 1.990 V
ConnectFailure - Unable to connect to the remote server No connection could be made because the target machine actively refused it -2 1.990 V
ConnectFailure - Unable to connect to the remote server No connection could be made because the target machine actively refused it -2 1.980 V
ConnectFailure - Unable to connect to the remote server No connection could be made because the target machine actively refused it -2 1.983 V
ConnectFailure - Unable to connect to the remote server No connection could be made because the target machine actively refused it

is blocked. Looks like a firewall.

Alternatively, the web server process might not be running at all for some reason.

…checked router both ports 80 & 443 point to this new macmini [all was working before ssl setup]
sudo apachectl configtest: OK
apache has been restarted


refused to connect
Will hit reply here, then restart router [nothing to lose!]