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Editorial Team
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Asked: 2026-05-11T18:23:06+00:00

I have enabled the Web Server on my Mac OS X (10.5.6) by going

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I have enabled the Web Server on my Mac OS X (10.5.6) by going to the System Preferences -> Internet & Network -> Sharing and clicking on the Web Server option. It gives me the IP address of my system as the Web Server, but even after clicking on it, it does not show the page, but gives an error: Failed to Connect

Any help on this would be wonderful.

I have tried with MAMP, but there, I am unable to get my own PHP pages to be displayed.

Starting and/or stopping the web server from the command line, gives me the following:

dyld: Symbol not found: _apr_socket_sendfile
  Referenced from: /usr/sbin/httpd
  Expected in: /usr/lib/libapr-1.0.dylib

Trace/BPT trap

The files on my box are:

~ $ ls -lrt /usr/lib/libapr*
-rwxr-xr-x  1 root  wheel  578640 Sep 23  2007 /usr/lib/libapr-1.0.2.7.dylib
-rwxr-xr-x  1 root  wheel  393696 Sep 23  2007 /usr/lib/libaprutil-1.0.2.7.dylib
-rwxrwxr-x  1 root  admin  569544 Oct 27 10:44 /usr/lib/libaprutil-1.0.2.12.dylib
-rwxrwxr-x  1 root  admin  835824 Oct 27 10:44 /usr/lib/libapr-1.0.2.12.dylib
lrwxr-xr-x  1 root  admin      25 Jan  4 22:28 /usr/lib/libaprutil-1.dylib -> libaprutil-1.0.2.12.dylib
lrwxr-xr-x  1 root  admin      25 Jan  4 22:28 /usr/lib/libaprutil-1.0.dylib -> libaprutil-1.0.2.12.dylib
lrwxr-xr-x  1 root  admin      21 Jan  4 22:28 /usr/lib/libapr-1.dylib -> libapr-1.0.2.12.dylib
lrwxr-xr-x  1 root  admin      21 Jan  4 22:28 /usr/lib/libapr-1.0.dylib -> libapr-1.0.2.12.dylib

The MD5 values are:

~ $ openssl md5 /usr/sbin/httpd /usr/lib/libapr-1.0.dylib 
MD5(/usr/sbin/httpd)= d5194790e9cfaca881d0e8fc3db24889
MD5(/usr/lib/libapr-1.0.dylib)= f7f7fd3cd315ca4e7c6ad2a2f222998e

The libapr-1.0.dylib is linked to the newer 1.0.2.12 version.

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1 Answer

  1. Editorial Team

    I’m having a similar problem and got to this page cause I feel lucky today 🙂
    The error means the httpd binary makes reference to a symbol that cannot be found in the appropriate dynamically linked library (libapr in this case, Apache Runtime Library)

    Running same OS X version on an iMac. /usr/lib/libapr-1.0.dylib points to the most recent version of the library (1.0.2.12), which does not define the method/symbol _apr_socket_sendfile

    The other version of libapr library is 1.0.2.7, does have that symbol. I had the symbolic links point to this version instead (also for libaprutil):

    // BEFORE (both 1.0.2.7 and 1.0.2.12 versions exist, symlinks point to .12)
bash-3.2# ls -l libapr*
-rwxr-xr-x  2 userna  wheel  835824 19 Sep  2008 libapr-1.0.2.12.dylib
-rwxr-xr-x  1 root    wheel  578640 24 Sep  2007 libapr-1.0.2.7.dylib
lrwxrwxrwx  1 root    wheel      21 14 Oct  2008 libapr-1.0.dylib -> libapr-1.0.2.12.dylib
lrwxrwxrwx  1 root    wheel      21 14 Oct  2008 libapr-1.dylib -> libapr-1.0.2.12.dylib
-rwxr-xr-x  2 userna  wheel  569544 19 Sep  2008 libaprutil-1.0.2.12.dylib
-rwxr-xr-x  1 root    wheel  393696 24 Sep  2007 libaprutil-1.0.2.7.dylib
lrwxrwxrwx  1 root    wheel      25 14 Oct  2008 libaprutil-1.0.dylib -> libaprutil-1.0.2.12.dylib
lrwxrwxrwx  1 root    wheel      25 14 Oct  2008 libaprutil-1.dylib -> libaprutil-1.0.2.12.dylib

// CHANGE symbolic links to previous version
bash-3.2# ln -sf libapr-1.0.2.7.dylib libapr-1.0.dylib
bash-3.2# ln -sf libapr-1.0.2.7.dylib libapr-1.dylib
bash-3.2# ln -sf libaprutil-1.0.2.7.dylib libaprutil-1.0.dylib
bash-3.2# ln -sf libaprutil-1.0.2.7.dylib libaprutil-1.dylib

// TESTing whether httpd is loaded and run
bash-3.2# /usr/sbin/httpd -t
Syntax OK

    Not really sure whether this has been broken since last software update that included Apache Web Server, I rarely use it on this box.

    Hope it helps 😉
    Jon

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