Index: python27/Makefile.version
===================================================================
--- python27/Makefile.version	(revision 494751)
+++ python27/Makefile.version	(working copy)
@@ -1,4 +1,4 @@
 # Mk/Uses/python.mk includes this file, don't remove it!
 # $FreeBSD$
 
-PYTHON_PORTVERSION=	2.7.15
+PYTHON_PORTVERSION=	2.7.16
Index: python27/distinfo
===================================================================
--- python27/distinfo	(revision 494751)
+++ python27/distinfo	(working copy)
@@ -1,3 +1,3 @@
-TIMESTAMP = 1525598061
-SHA256 (python/Python-2.7.15.tar.xz) = 22d9b1ac5b26135ad2b8c2901a9413537e08749a753356ee913c84dbd2df5574
-SIZE (python/Python-2.7.15.tar.xz) = 12642436
+TIMESTAMP = 1551829403
+SHA256 (python/Python-2.7.16.tar.xz) = f222ef602647eecb6853681156d32de4450a2c39f4de93bd5b20235f2e660ed7
+SIZE (python/Python-2.7.16.tar.xz) = 12752104
Index: python27/pkg-plist
===================================================================
--- python27/pkg-plist	(revision 494751)
+++ python27/pkg-plist	(working copy)
@@ -1436,8 +1436,8 @@
 lib/python2.7/ensurepip/__main__.py
 lib/python2.7/ensurepip/__main__.pyc
 lib/python2.7/ensurepip/__main__.pyo
-lib/python2.7/ensurepip/_bundled/pip-9.0.3-py2.py3-none-any.whl
-lib/python2.7/ensurepip/_bundled/setuptools-39.0.1-py2.py3-none-any.whl
+lib/python2.7/ensurepip/_bundled/pip-18.1-py2.py3-none-any.whl
+lib/python2.7/ensurepip/_bundled/setuptools-40.6.2-py2.py3-none-any.whl
 lib/python2.7/ensurepip/_uninstall.py
 lib/python2.7/ensurepip/_uninstall.pyc
 lib/python2.7/ensurepip/_uninstall.pyo
@@ -2003,6 +2003,9 @@
 lib/python2.7/lib-tk/test/test_tkinter/test_loadtk.py
 lib/python2.7/lib-tk/test/test_tkinter/test_loadtk.pyc
 lib/python2.7/lib-tk/test/test_tkinter/test_loadtk.pyo
+lib/python2.7/lib-tk/test/test_tkinter/test_misc.py
+lib/python2.7/lib-tk/test/test_tkinter/test_misc.pyc
+lib/python2.7/lib-tk/test/test_tkinter/test_misc.pyo
 lib/python2.7/lib-tk/test/test_tkinter/test_text.py
 lib/python2.7/lib-tk/test/test_tkinter/test_text.pyc
 lib/python2.7/lib-tk/test/test_tkinter/test_text.pyo
@@ -2726,9 +2729,9 @@
 lib/python2.7/test/badsyntax_future8.py
 lib/python2.7/test/badsyntax_future9.py
 lib/python2.7/test/badsyntax_nocaret.py
-lib/python2.7/test/bisect.py
-lib/python2.7/test/bisect.pyc
-lib/python2.7/test/bisect.pyo
+lib/python2.7/test/bisect_cmd.py
+lib/python2.7/test/bisect_cmd.pyc
+lib/python2.7/test/bisect_cmd.pyo
 lib/python2.7/test/capath/0e4015b9.0
 lib/python2.7/test/capath/4e1295a3.0
 lib/python2.7/test/capath/5ed36f99.0
@@ -2914,7 +2917,6 @@
 lib/python2.7/test/decimaltestdata/tointegral.decTest
 lib/python2.7/test/decimaltestdata/tointegralx.decTest
 lib/python2.7/test/decimaltestdata/xor.decTest
-lib/python2.7/test/dh1024.pem
 lib/python2.7/test/doctest_aliases.py
 lib/python2.7/test/doctest_aliases.pyc
 lib/python2.7/test/doctest_aliases.pyo
@@ -2923,6 +2925,7 @@
 lib/python2.7/test/double_const.pyo
 lib/python2.7/test/empty.vbs
 lib/python2.7/test/exception_hierarchy.txt
+lib/python2.7/test/ffdh3072.pem
 lib/python2.7/test/floating_points.txt
 lib/python2.7/test/fork_wait.py
 lib/python2.7/test/fork_wait.pyc
@@ -3065,6 +3068,7 @@
 lib/python2.7/test/symlink_support.py
 lib/python2.7/test/symlink_support.pyc
 lib/python2.7/test/symlink_support.pyo
+lib/python2.7/test/talos-2019-0758.pem
 lib/python2.7/test/test_MimeWriter.py
 lib/python2.7/test/test_MimeWriter.pyc
 lib/python2.7/test/test_MimeWriter.pyo
@@ -3140,6 +3144,9 @@
 lib/python2.7/test/test_bastion.py
 lib/python2.7/test/test_bastion.pyc
 lib/python2.7/test/test_bastion.pyo
+lib/python2.7/test/test_bdb.py
+lib/python2.7/test/test_bdb.pyc
+lib/python2.7/test/test_bdb.pyo
 lib/python2.7/test/test_bigaddrspace.py
 lib/python2.7/test/test_bigaddrspace.pyc
 lib/python2.7/test/test_bigaddrspace.pyo
@@ -4320,7 +4327,6 @@
 lib/python2.7/test/win_console_handler.py
 lib/python2.7/test/win_console_handler.pyc
 lib/python2.7/test/win_console_handler.pyo
-lib/python2.7/test/wrongcert.pem
 lib/python2.7/test/xmltestdata/expat224_utf8_bug.xml
 lib/python2.7/test/xmltestdata/simple-ns.xml
 lib/python2.7/test/xmltestdata/simple.xml
Index: python-doc-html/distinfo
===================================================================
--- python-doc-html/distinfo	(revision 494751)
+++ python-doc-html/distinfo	(working copy)
@@ -1,12 +1,12 @@
-TIMESTAMP = 1549906249
-SHA256 (python/python-2.7.15-docs-html.tar.bz2) = 5582aa8f59c2d5457ae87e266000f9ef75ed041a02fa72bd988a5169aae8ebde
-SIZE (python/python-2.7.15-docs-html.tar.bz2) = 4627519
-SHA256 (python/python-2.7.15-docs-pdf-a4.tar.bz2) = f747ca034cae426876017c37dfac0648ae535ad0b95d1e3a27385feee602d956
-SIZE (python/python-2.7.15-docs-pdf-a4.tar.bz2) = 9429818
-SHA256 (python/python-2.7.15-docs-pdf-letter.tar.bz2) = 698413a74cfa5453a95a12ec34f6cc82e19e4ef53ebad4d736fe608d64f14267
-SIZE (python/python-2.7.15-docs-pdf-letter.tar.bz2) = 9429554
-SHA256 (python/python-2.7.15-docs-text.tar.bz2) = 92b32e57182b1b7110f71db43a8c49aaaf9833186d7ea1021fe3b166e7164535
-SIZE (python/python-2.7.15-docs-text.tar.bz2) = 1617467
+TIMESTAMP = 1551837193
+SHA256 (python/python-2.7.16-docs-html.tar.bz2) = 02d488e908ceaa793662c3ea17ee9b9259f32782d74705633151c19f5fd05fe5
+SIZE (python/python-2.7.16-docs-html.tar.bz2) = 4629448
+SHA256 (python/python-2.7.16-docs-pdf-a4.tar.bz2) = b8397a5ba1c8a205a9873c12899dd33c0d5f265abaad33ce200f2e9aad0fb492
+SIZE (python/python-2.7.16-docs-pdf-a4.tar.bz2) = 9508359
+SHA256 (python/python-2.7.16-docs-pdf-letter.tar.bz2) = 404bb54c31ee317714f10614882d7eec39ecf99c0535b4c3b0359c8a88453105
+SIZE (python/python-2.7.16-docs-pdf-letter.tar.bz2) = 9508486
+SHA256 (python/python-2.7.16-docs-text.tar.bz2) = 79005c4bf4b4d07391fc60573671437b7c6723f3dc5b82cc0880ede929d747b5
+SIZE (python/python-2.7.16-docs-text.tar.bz2) = 1632463
 SHA256 (python/python-3.6.8-docs-html.tar.bz2) = d17ebdc57a6590b7c86c98047c4f90723c5a1846343a4640e0596161922cf9eb
 SIZE (python/python-3.6.8-docs-html.tar.bz2) = 6010329
 SHA256 (python/python-3.6.8-docs-pdf-a4.tar.bz2) = 4734db2cea99bbd2d3b6523cc3aa969c88cebfce7c705e8918677fce96cdd1c8