Index: pym/portage.py
===================================================================
--- pym/portage.py	(revision 9759)
+++ pym/portage.py	(revision 9760)
@@ -4234,12 +4234,34 @@
 					if droppriv:
 						st = os.stat(mydir)
 						if st.st_gid != portage_gid or \
-							not stat.S_IMODE(st.st_mode) & dirmode:
+							not dirmode == (stat.S_IMODE(st.st_mode) & dirmode):
 							droppriv_fix = True
+						if not droppriv_fix:
+							# Check permissions of files in the directory.
+							for filename in os.listdir(mydir):
+								try:
+									subdir_st = os.lstat(
+										os.path.join(mydir, filename))
+								except OSError:
+									continue
+								if subdir_st.st_gid != portage_gid or \
+									((stat.S_ISDIR(subdir_st.st_mode) and \
+									not dirmode == (stat.S_IMODE(subdir_st.st_mode) & dirmode)) or \
+									(not stat.S_ISDIR(subdir_st.st_mode) and \
+									not filemode == (stat.S_IMODE(subdir_st.st_mode) & filemode))):
+									droppriv_fix = True
+									break
+					if droppriv_fix:
+						writemsg(colorize("WARN", " * ") + \
+							 "Adjusting permissions " + \
+							 "for FEATURES=userpriv: '%s'\n" % mydir,
+							noiselevel=-1)
+					elif modified:
+						writemsg(colorize("WARN", " * ") + \
+							 "Adjusting permissions " + \
+							 "for FEATURES=%s: '%s'\n" % (myfeature, mydir),
+							noiselevel=-1)
 					if modified or kwargs["always_recurse"] or droppriv_fix:
-						if modified:
-							writemsg("Adjusting permissions recursively: '%s'\n" % mydir,
-								noiselevel=-1)
 						def onerror(e):
 							raise	# The feature is disabled if a single error
 									# occurs during permissions adjustment.