It seems that it's impossible to handle path names longer than 255 characters with Aapache on FreeBSD. It seems to me like it may be a compilation time bug of devel/apr1 Following code fragments seems to be key in observed behaviour ------------------------------------------------------------------------------ /* header files for PATH_MAX, _POSIX_PATH_MAX */ #if APR_HAVE_LIMITS_H #include <limits.h> #else #if APR_HAVE_SYS_SYSLIMITS_H #include <sys/syslimits.h> #endif #endif ------------------------------------------------------------------------------ and ------------------------------------------------------------------------------ #if defined(PATH_MAX) #define APR_PATH_MAX PATH_MAX #elif defined(_POSIX_PATH_MAX) #define APR_PATH_MAX _POSIX_PATH_MAX #else #error no decision has been made on APR_PATH_MAX for your platform #endif ------------------------------------------------------------------------------ During configure I get following messages ------------------------------------------------------------------------------ checking for limits.h... (cached) yes (...) checking sys/syslimits.h usability... yes checking sys/syslimits.h presence... no configure: WARNING: sys/syslimits.h: accepted by the compiler, rejected by the preprocessor! configure: WARNING: sys/syslimits.h: proceeding with the compiler's result checking for sys/syslimits.h... yes ------------------------------------------------------------------------------ It seems like limits.h of following content is being chosen: ------------------------------------------------------------------------------ #define _POSIX_PATH_MAX 255 ------------------------------------------------------------------------------ And file /usr/include/sys/syslimits.h : ------------------------------------------------------------------------------ #define PATH_MAX 1024 /* max bytes in pathname */ ------------------------------------------------------------------------------ It's interesting that at least my Ubuntu has file linux/limits.h with only following value defined for PATH_MAX ------------------------------------------------------------------------------ #define PATH_MAX 4096 /* # chars in a path name including nul */ ------------------------------------------------------------------------------