diff -r 556a11c11edd PCbuild/build_ssl.py
--- a/PCbuild/build_ssl.py	Mon Sep 05 22:24:01 2016 -0400
+++ b/PCbuild/build_ssl.py	Tue Sep 06 23:00:18 2016 -0400
@@ -205,33 +205,31 @@
         if arch == "amd64" and os.path.isfile(m32) and not os.path.isfile(makefile):
             os.unlink(m32)
 
-        # If the ssl makefiles do not exist, we invoke Perl to generate them.
-        # Due to a bug in this script, the makefile sometimes ended up empty
-        # Force a regeneration if it is.
-        if not os.path.isfile(makefile) or os.path.getsize(makefile)==0:
-            if perl is None:
-                print("Perl is required to build the makefiles!")
-                sys.exit(1)
+        # Always create the makefile, even if it exists, we need up-to-date
+        # buildinf and opensslconf files.
+        if perl is None:
+            print("Perl is required to build the makefiles!")
+            sys.exit(1)
 
-            print("Creating the makefiles...")
-            sys.stdout.flush()
-            # Put our working Perl at the front of our path
-            os.environ["PATH"] = os.path.dirname(perl) + \
-                                          os.pathsep + \
-                                          os.environ["PATH"]
-            run_configure(configure, do_script)
-            if debug:
-                print("OpenSSL debug builds aren't supported.")
-            #if arch=="x86" and debug:
-            #    # the do_masm script in openssl doesn't generate a debug
-            #    # build makefile so we generate it here:
-            #    os.system("perl util\mk1mf.pl debug "+configure+" >"+makefile)
+        print("Creating the makefiles...")
+        sys.stdout.flush()
+        # Put our working Perl at the front of our path
+        os.environ["PATH"] = os.path.dirname(perl) + \
+                                        os.pathsep + \
+                                        os.environ["PATH"]
+        run_configure(configure, do_script)
+        if debug:
+            print("OpenSSL debug builds aren't supported.")
+        #if arch=="x86" and debug:
+        #    # the do_masm script in openssl doesn't generate a debug
+        #    # build makefile so we generate it here:
+        #    os.system("perl util\mk1mf.pl debug "+configure+" >"+makefile)
 
-            if arch == "amd64":
-                create_makefile64(makefile, m32)
-            fix_makefile(makefile)
-            copy(r"crypto\buildinf.h", r"crypto\buildinf_%s.h" % arch)
-            copy(r"crypto\opensslconf.h", r"crypto\opensslconf_%s.h" % arch)
+        if arch == "amd64":
+            create_makefile64(makefile, m32)
+        fix_makefile(makefile)
+        copy(r"crypto\buildinf.h", r"crypto\buildinf_%s.h" % arch)
+        copy(r"crypto\opensslconf.h", r"crypto\opensslconf_%s.h" % arch)
 
         # If the assembler files don't exist in tmpXX, copy them there
         if perl is None and os.path.exists("asm"+dirsuffix):
diff -r 556a11c11edd PCbuild/get_externals.bat
--- a/PCbuild/get_externals.bat	Mon Sep 05 22:24:01 2016 -0400
+++ b/PCbuild/get_externals.bat	Tue Sep 06 23:00:18 2016 -0400
@@ -54,7 +54,7 @@
 for %%e in (
             bzip2-1.0.6
             nasm-2.11.06
-            openssl-1.0.2d
+            openssl-1.0.2h
             tcl-8.6.1.0
             tk-8.6.1.0
             tix-8.4.3.4
diff -r 556a11c11edd PCbuild/pyproject.props
--- a/PCbuild/pyproject.props	Mon Sep 05 22:24:01 2016 -0400
+++ b/PCbuild/pyproject.props	Tue Sep 06 23:00:18 2016 -0400
@@ -20,7 +20,7 @@
     <sqlite3Dir>$(externalsDir)\sqlite-3.8.11.0</sqlite3Dir>
     <bz2Dir>$(externalsDir)\bzip2-1.0.6</bz2Dir>
     <lzmaDir>$(externalsDir)\xz-5.0.5</lzmaDir>
-    <opensslDir>$(externalsDir)\openssl-1.0.2d</opensslDir>
+    <opensslDir>$(externalsDir)\openssl-1.0.2h</opensslDir>
     <tcltkDir>$(externalsDir)\tcltk</tcltkDir>
     <tcltk64Dir>$(externalsDir)\tcltk64</tcltk64Dir>
     <tcltkLib>$(tcltkDir)\lib\tcl86t.lib;$(tcltkDir)\lib\tk86t.lib</tcltkLib>
diff -r 556a11c11edd PCbuild/readme.txt
--- a/PCbuild/readme.txt	Mon Sep 05 22:24:01 2016 -0400
+++ b/PCbuild/readme.txt	Tue Sep 06 23:00:18 2016 -0400
@@ -171,7 +171,7 @@
     Homepage:
         http://tukaani.org/xz/
 _ssl
-    Python wrapper for version 1.0.2d of the OpenSSL secure sockets
+    Python wrapper for version 1.0.2h of the OpenSSL secure sockets
     library, which is built by ssl.vcxproj
     Homepage:
         http://www.openssl.org/