That looks pretty good! I'm gratified that you took my suggestion and ran with it. Thanks for sharing it with us! Looking at what you have, I think it could be made a bit more compact.

use File::Path qw( mkpath );

my $base_path = '/my/base/path';
my $init_done = 0;
my %paths = ();

INIT:
while ( ! $init_done ) {
    $init_done
        = eval { Log::Log4perl->init_once($LOGGER_CONF_FILE); 1 };

    # If there's an error, and it's THIS one,
    if ( $@ =~ m{\A Can't \s open \s
                 \Q$base_path\E (?: / ( \S+ ) )? / [^/]+ \s
                 \( No \s such \s file \s or \s directory \)}xms )
    {
        # This is the path that's missing
        my $target_path = "$base_path/$1";
        
        # If we've already tried to create it once, don't try again
        if ( $paths{ $target_path }++ ) {
            last INIT;
        }
        
        # Try to create the path
        eval { mkpath( $target_path ) };
        if ( ! -d $target_path ) {
            warn "Can't create missing directory '$target_path': $@\n"
+;
        }
    }
}

# if we couldn't get the config file to initlize, load a blank one and
+ move on without logging
if ( ! $init_done ) {
    warn "Couldn't initilize logger, defaulting to blank config file";
    Log::Log4perl->init( \'' );
}
[download]

Note the differences, though (good and bad).

• I use File::Path::mkpath instead of just mkdir. This will try to create every necessary directory right up to the root. Yours won't try to create anything above /my/base/path. If attempting to create directories above /my/base/path will be a problem, you should go back to your own code.
• Instead of tracking $init_fail, I track $init_done. This way the while condition is more natural (and doesn't look infinite), and I get to set it in only one place inside the loop.
• I use Log::Log4perl->init with an empty string instead of an empty file I just created. It's shorter, and I don't run the risk of failing to create the empty file.
• I re-complicated the regular expression (in particular adding the /x form back).
• I haven't tested this. There could even be a syntax error.

Thanks again for posting your work.

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