diff --git a/Misc/NEWS.d/next/Windows/2019-09-16-12-47-12.bpo-38117.JaiB0X.rst b/Misc/NEWS.d/next/Windows/2019-09-16-12-47-12.bpo-38117.JaiB0X.rst
new file mode 100644
index 00000000000..35e1cabb9b4
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2019-09-16-12-47-12.bpo-38117.JaiB0X.rst
@@ -0,0 +1 @@
+Updates bundled OpenSSL to 1.0.2t
diff --git a/PCbuild/get_external.py b/PCbuild/get_external.py
index a682d3849f1..10dacdd984d 100644
--- a/PCbuild/get_external.py
+++ b/PCbuild/get_external.py
@@ -1,12 +1,16 @@
 #!/usr/bin/env python3
 
+# We do not need to import built modules from PCbuild (duh), so
+# filter those out here to save Steve from debugging it yet again.
+import sys
+sys.path[:] = [p for p in sys.path if p and 'PCbuild' not in p]
+
 import argparse
 import os
 import pathlib
 import zipfile
 from urllib.request import urlretrieve
 
-
 def fetch_zip(commit_hash, zip_dir, *, org='python', binary=False, verbose):
     repo = f'cpython-{"bin" if binary else "source"}-deps'
     url = f'https://github.com/{org}/{repo}/archive/{commit_hash}.zip'
diff --git a/PCbuild/get_externals.bat b/PCbuild/get_externals.bat
index eba19492d94..9f1b09e9b65 100644
--- a/PCbuild/get_externals.bat
+++ b/PCbuild/get_externals.bat
@@ -47,7 +47,7 @@ rem files in both this dir and PC\VS9.0
 set libraries=
 set libraries=%libraries%                                    bzip2-1.0.6
 if NOT "%IncludeBsddb%"=="false" set libraries=%libraries%   bsddb-4.7.25.0
-if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2s
+if NOT "%IncludeSSL%"=="false" set libraries=%libraries%     openssl-1.0.2t
 set libraries=%libraries%                                    sqlite-3.28.0.0
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tcl-8.5.19.0
 if NOT "%IncludeTkinter%"=="false" set libraries=%libraries% tk-8.5.19.0
diff --git a/PCbuild/python.props b/PCbuild/python.props
index 355bb3f0523..f0b531e50eb 100644
--- a/PCbuild/python.props
+++ b/PCbuild/python.props
@@ -35,7 +35,7 @@
     <sqlite3Dir>$(ExternalsDir)sqlite-3.28.0.0\</sqlite3Dir>
     <bz2Dir>$(ExternalsDir)bzip2-1.0.6\</bz2Dir>
     <bsddbDir>$(ExternalsDir)bsddb-4.7.25.0</bsddbDir>
-    <opensslDir>$(ExternalsDir)openssl-1.0.2s\</opensslDir>
+    <opensslDir>$(ExternalsDir)openssl-1.0.2t\</opensslDir>
     <opensslIncludeDir>$(opensslDir)include32</opensslIncludeDir>
     <opensslIncludeDir Condition="'$(ArchName)' == 'amd64'">$(opensslDir)include64</opensslIncludeDir>
     <nasmDir>$(ExternalsDir)\nasm-2.11.06\</nasmDir>