diff --git a/autoconf/m4/unreal.m4 b/autoconf/m4/unreal.m4
index 5a93300a8..e3eac1b52 100644
--- a/autoconf/m4/unreal.m4
+++ b/autoconf/m4/unreal.m4
@@ -140,13 +140,13 @@ dnl the following 2 macros are based on CHECK_SSL by Mark Ethan Trostler <trostl
 AC_DEFUN([CHECK_SSL],
 [
 AC_ARG_ENABLE(ssl,
-	[AC_HELP_STRING([--enable-ssl=],[enable ssl will check /usr/local/ssl /usr/lib/ssl /usr/ssl /usr/pkg /usr/sfw /usr/local /usr])],
+	[AC_HELP_STRING([--enable-ssl=],[enable ssl will check /usr/local/opt/openssl /usr/local/ssl /usr/lib/ssl /usr/ssl /usr/pkg /usr/sfw /usr/local /usr])],
 	[],
 	[enable_ssl=no])
 AS_IF([test $enable_ssl != "no"],
 	[ 
 	AC_MSG_CHECKING([for openssl])
-	for dir in $enable_ssl /usr/local/ssl /usr/lib/ssl /usr/ssl /usr/pkg /usr/sfw /usr/local /usr; do
+	for dir in $enable_ssl /usr/local/opt/openssl /usr/local/ssl /usr/lib/ssl /usr/ssl /usr/pkg /usr/sfw /usr/local /usr; do
 		ssldir="$dir"
 		if test -f "$dir/include/openssl/ssl.h"; then
 			AC_MSG_RESULT([found in $ssldir/include/openssl])
diff --git a/configure b/configure
index 716341471..fb56e4325 100755
--- a/configure
+++ b/configure
@@ -1396,8 +1396,9 @@ Optional Features:
   --enable-hardening      Enable compiler and linker options to frustrate
                           memory corruption exploits [yes]
   --disable-prefixaq      Disable chanadmin (+a) and chanowner (+q) prefixes
-  --enable-ssl=           enable ssl will check /usr/local/ssl /usr/lib/ssl
-                          /usr/ssl /usr/pkg /usr/sfw /usr/local /usr
+  --enable-ssl=           enable ssl will check /usr/local/opt/openssl
+                          /usr/local/ssl /usr/lib/ssl /usr/ssl /usr/pkg
+                          /usr/sfw /usr/local /usr
   --disable-dynamic-linking
                           Make the IRCd statically link with shared objects
                           rather than dynamically (noone knows if disabling
@@ -7266,7 +7267,7 @@ if test $enable_ssl != "no"; then :
 
 	{ $as_echo "$as_me:${as_lineno-$LINENO}: checking for openssl" >&5
 $as_echo_n "checking for openssl... " >&6; }
-	for dir in $enable_ssl /usr/local/ssl /usr/lib/ssl /usr/ssl /usr/pkg /usr/sfw /usr/local /usr; do
+	for dir in $enable_ssl /usr/local/opt/openssl /usr/local/ssl /usr/lib/ssl /usr/ssl /usr/pkg /usr/sfw /usr/local /usr; do
 		ssldir="$dir"
 		if test -f "$dir/include/openssl/ssl.h"; then
 			{ $as_echo "$as_me:${as_lineno-$LINENO}: result: found in $ssldir/include/openssl" >&5