diff --git a/playground/boost/waf.bat b/playground/boost/waf.bat
index ec97c98f..a96f2f84 100644
--- a/playground/boost/waf.bat
+++ b/playground/boost/waf.bat
@@ -1,3 +1,10 @@
 @echo off
+
 rem path are automatically detected on Linux
-python waf --boost-includes=c:\boost_1_45_0 --boost-libs=c:\boost_1_45_0\stage\lib %1 %2 %3
+set BOOST_PATH=e:\project\libs\boost_1_55_0
+set BOOST_LIB=%BOOST_PATH%\lib32-msvc-12.0
+
+set LIB=%BOOST_LIB%
+set INCLUDE=%BOOST_PATH%
+
+python waf --boost-linkage_autodetect --boost-python=27 %*
diff --git a/playground/boost/wscript b/playground/boost/wscript
index e15fa8e8..16b9c39a 100644
--- a/playground/boost/wscript
+++ b/playground/boost/wscript
@@ -6,7 +6,7 @@ def options(opt):
 
 def configure(conf):
     conf.load('compiler_cxx boost')
-    conf.check_boost('system filesystem', mt=True)
+    conf.check_boost('system filesystem python', mt=True)
 
 def build(bld):
     bld.program(source='main.cpp', target='app', use='BOOST')
diff --git a/waflib/extras/boost.py b/waflib/extras/boost.py
index 543e0aa3..20e0ac22 100644
--- a/waflib/extras/boost.py
+++ b/waflib/extras/boost.py
@@ -229,6 +229,7 @@ def boost_get_libs(self, *k, **kw):
 	according to the parameters
 	'''
 	path, files = self.__boost_get_libs_path(**kw)
+	files = sorted(files, key=lambda f: len(f.name), reverse=True)
 	toolset = self.boost_get_toolset(kw.get('toolset', ''))
 	toolset_pat = '(-%s[0-9]{0,3})' % toolset
 	version = '(-%s)' % self.env.BOOST_VERSION
@@ -260,7 +261,10 @@ def boost_get_libs(self, *k, **kw):
 		tags_pat = t and ''.join(t) or ''
 		for lib in lib_names:
 			if lib == 'python':
-				tags = '%s?(-py%s)?' % (tags_pat, kw['python'])
+			   # for instance, with python='27',
+			   # accepts '-py27', '-py2', '27' and '2'
+			   # but will reject '-py3', '-py26', '26' and '3'
+				tags = '({0})?((-py{2})|(-py{1}(?=[^0-9]))|({2})|({1}(?=[^0-9]))|(?=[^0-9])(?!-py))'.format(tags_pat, kw['python'][0], kw['python'])
 			else:
 				tags = tags_pat
 			# Trying libraries, from most strict match to least one