diff --git a/generate/templates/templates/binding.gyp b/generate/templates/templates/binding.gyp
index a332fc74c..dbe70ab5c 100644
--- a/generate/templates/templates/binding.gyp
+++ b/generate/templates/templates/binding.gyp
@@ -39,7 +39,7 @@
           "actions": [{
             "action_name": "acquire",
             "action": ["node", "utils/acquireOpenSSL.js"],
-            "inputs": ["vendor/openssl_distributions.json"],
+            "inputs": ["vendor/static_config/openssl_distributions.json"],
             "outputs": ["vendor/openssl"],
             "message": "Acquiring OpensSL binaries and headers"
           }]
diff --git a/utils/README.md b/utils/README.md
index ce679f8ef..1773e9979 100644
--- a/utils/README.md
+++ b/utils/README.md
@@ -11,10 +11,10 @@
   * Mac: clang-8.1 or clang-9.
   * Windows: vs12, vs14, vs15
 
-  The discovered distributions are written into `vendor/openssl_distributions.json`. This script does not need to be run unless you are updating the version of OpenSSL to build against.
+  The discovered distributions are written into `vendor/static_config/openssl_distributions.json`. This script does not need to be run unless you are updating the version of OpenSSL to build against.
 
-  ### acquireOpenSSL
-  Download the OpenSSL binaries and headers applicable to the current OS for the latest compiler version (clang-9/vs14). Uses links from `vendor/openssl_distributions.json`.
+  ## acquireOpenSSL
+  Download the OpenSSL binaries and headers applicable to the current OS for the latest compiler version (clang-9/vs14). Uses links from `vendor/static_config/openssl_distributions.json`.
   
   TODO:
   * Make the script pull the debug versions if node-gyp is building in debug mode
diff --git a/utils/acquireOpenSSL.js b/utils/acquireOpenSSL.js
index 2dc54780c..1c1ca29df 100644
--- a/utils/acquireOpenSSL.js
+++ b/utils/acquireOpenSSL.js
@@ -7,7 +7,7 @@ const tar = require("tar-fs");
 const zlib = require("zlib");
 
 const vendorPath = path.resolve(__dirname, "..", "vendor");
-const distrosFilePath = path.join(vendorPath, "openssl_distributions.json");
+const distrosFilePath = path.join(vendorPath, "static_config", "openssl_distributions.json");
 const extractPath = path.join(vendorPath, "openssl");
 
 const getOSName = () => {
diff --git a/utils/configureLibssh2.js b/utils/configureLibssh2.js
index 401cb5fc9..3ee8cd933 100644
--- a/utils/configureLibssh2.js
+++ b/utils/configureLibssh2.js
@@ -1,31 +1,33 @@
 var cp = require("child_process");
+var fse = require('fs-extra');
 var path = require("path");
-var rooted = function (dir) {
-  var fullPath = path.join(__dirname, "..", dir);
-  var escapedPathForShell = fullPath.replace(/ /g, "\\ ");
-  return escapedPathForShell;
-};
+
+const libssh2VendorDirectory = path.resolve(__dirname, "..", "vendor", "libssh2");
+const libssh2ConfigureScript = path.join(libssh2VendorDirectory, "configure");
+const libssh2StaticConfigDirectory  = path.resolve(__dirname, "..", "vendor", "static_config", "libssh2");
 
 module.exports = function retrieveExternalDependencies() {
-  if (process.platform === "win32") {
-    return Promise.resolve("");
+  console.info("[nodegit] Configuring libssh2.");
+
+  // Copy Windows / Mac preconfigured files
+  if (process.platform === "win32" || process.platform === "darwin") {
+    return fse.copy(
+      path.join(libssh2StaticConfigDirectory, process.platform),
+      path.join(libssh2VendorDirectory, "src")
+    );
   }
 
+  // Run the `configure` script on Linux
   return new Promise(function(resolve, reject) {
-    console.info("[nodegit] Configuring libssh2.");
+
     var opensslDir = process.argv[2];
     var isElectron = process.argv[3] === "1";
     var opensslIncludes = isElectron ? path.join(opensslDir, "includes") : opensslDir;
 
     var newEnv = {};
-
-    // For some magic reason, MacOS fails to build if we copy over the current environment variables, but Linux
-    // builds fail if we DON'T copy over the current environment variables
-    if (process.platform !== "darwin") {
-      Object.keys(process.env).forEach(function(key) {
-        newEnv[key] = process.env[key];
-      });
-    }
+    Object.keys(process.env).forEach(function(key) {
+      newEnv[key] = process.env[key];
+    });
 
     newEnv.CPPFLAGS = newEnv.CPPFLAGS || "";
     newEnv.CPPFLAGS += ` -I${opensslIncludes}`;
@@ -37,8 +39,11 @@ module.exports = function retrieveExternalDependencies() {
     }
 
     cp.exec(
-      rooted("vendor/libssh2/configure") + maybeLibsslPrefix,
-      {cwd: rooted("vendor/libssh2/"), env: newEnv},
+      libssh2ConfigureScript + maybeLibsslPrefix,
+      {
+        cwd: libssh2VendorDirectory,
+        env: newEnv
+      },
       function(err, stdout, stderr) {
         if (err) {
           console.error(err);
@@ -55,10 +60,5 @@ module.exports = function retrieveExternalDependencies() {
 
 // Called on the command line
 if (require.main === module) {
-  if (process.platform === "win32") {
-    console.log("nothing to do");
-  }
-  else {
-    module.exports();
-  }
+  module.exports();
 }
diff --git a/utils/discoverOpenSSLDistros.js b/utils/discoverOpenSSLDistros.js
index f0f6bc94e..5a413a8e6 100644
--- a/utils/discoverOpenSSLDistros.js
+++ b/utils/discoverOpenSSLDistros.js
@@ -171,10 +171,14 @@ const discoverDistributions = (treeHtml) => {
   );
 }
 
-const outputPath = path.resolve(__dirname, "..", "vendor", "openssl_distributions.json");
+const writeFile = (distributions) =>
+  fse.ensureDir(path.dirname(outputPath))
+    .then(fse.writeFile(outputPath, JSON.stringify(distributions, null, 2)));
+
+const outputPath = path.resolve(__dirname, "..", "vendor", "static_config", "openssl_distributions.json");
 request(getDistributionsRootURL())
   .then(discoverDistributions)
   .then(R.filter(R.identity))
   .then(R.sortBy(R.prop(0)))
   .then(R.fromPairs)
-  .then(distributions => fse.writeFile(outputPath, JSON.stringify(distributions, null, 2)));
+  .then(writeFile);
diff --git a/vendor/libgit2.gyp b/vendor/libgit2.gyp
index 6593372cc..11904835e 100644
--- a/vendor/libgit2.gyp
+++ b/vendor/libgit2.gyp
@@ -539,7 +539,7 @@
       "conditions": [
         ["OS=='mac' and node_root_dir.split('/')[-1].startswith('iojs')", {
           "include_dirs": [
-            "openssl/include"
+            "openssl/include",
           ]
         }],
         ["OS=='win'", {
@@ -561,7 +561,6 @@
           ],
           "include_dirs": [
             "libssh2/src",
-            "libssh2/win32",
             "libssh2/include"
           ],
           "defines!": [
@@ -570,7 +569,6 @@
           "direct_dependent_settings": {
             "include_dirs": [
               "libssh2/src",
-              "libssh2/win32",
               "libssh2/include"
             ]
           }
diff --git a/vendor/static_config/libssh2/darwin/libssh2_config.h b/vendor/static_config/libssh2/darwin/libssh2_config.h
new file mode 100644
index 000000000..eb3228e6c
--- /dev/null
+++ b/vendor/static_config/libssh2/darwin/libssh2_config.h
@@ -0,0 +1,262 @@
+/* src/libssh2_config.h.  Generated from libssh2_config.h.in by configure.  */
+/* src/libssh2_config.h.in.  Generated from configure.ac by autoheader.  */
+
+/* Define if building universal (internal helper macro) */
+/* #undef AC_APPLE_UNIVERSAL_BUILD */
+
+/* Define to one of `_getb67', `GETB67', `getb67' for Cray-2 and Cray-YMP
+   systems. This function is required for `alloca.c' support on those systems.
+   */
+/* #undef CRAY_STACKSEG_END */
+
+/* Define to 1 if using `alloca.c'. */
+/* #undef C_ALLOCA */
+
+/* Define to 1 if you have `alloca', as a function or macro. */
+#define HAVE_ALLOCA 1
+
+/* Define to 1 if you have <alloca.h> and it should be used (not on Ultrix).
+   */
+#define HAVE_ALLOCA_H 1
+
+/* Define to 1 if you have the <arpa/inet.h> header file. */
+#define HAVE_ARPA_INET_H 1
+
+/* Define to 1 if you have the declaration of `SecureZeroMemory', and to 0 if
+   you don't. */
+/* #undef HAVE_DECL_SECUREZEROMEMORY */
+
+/* disabled non-blocking sockets */
+/* #undef HAVE_DISABLED_NONBLOCKING */
+
+/* Define to 1 if you have the <dlfcn.h> header file. */
+#define HAVE_DLFCN_H 1
+
+/* Define to 1 if you have the <errno.h> header file. */
+#define HAVE_ERRNO_H 1
+
+/* Define to 1 if you have the `EVP_aes_128_ctr' function. */
+#define HAVE_EVP_AES_128_CTR 1
+
+/* Define to 1 if you have the <fcntl.h> header file. */
+#define HAVE_FCNTL_H 1
+
+/* use FIONBIO for non-blocking sockets */
+/* #undef HAVE_FIONBIO */
+
+/* Define to 1 if you have the `gettimeofday' function. */
+#define HAVE_GETTIMEOFDAY 1
+
+/* Define to 1 if you have the <inttypes.h> header file. */
+#define HAVE_INTTYPES_H 1
+
+/* use ioctlsocket() for non-blocking sockets */
+/* #undef HAVE_IOCTLSOCKET */
+
+/* use Ioctlsocket() for non-blocking sockets */
+/* #undef HAVE_IOCTLSOCKET_CASE */
+
+/* Define if you have the bcrypt library. */
+/* #undef HAVE_LIBBCRYPT */
+
+/* Define if you have the crypt32 library. */
+/* #undef HAVE_LIBCRYPT32 */
+
+/* Define if you have the gcrypt library. */
+/* #undef HAVE_LIBGCRYPT */
+
+/* Define if you have the mbedtls library. */
+/* #undef HAVE_LIBMBEDTLS */
+
+/* Define if you have the ssl library. */
+#define HAVE_LIBSSL 1
+
+/* Define if you have the z library. */
+#define HAVE_LIBZ 1
+
+/* Define to 1 if the compiler supports the 'long long' data type. */
+#define HAVE_LONGLONG 1
+
+/* Define to 1 if you have the <memory.h> header file. */
+#define HAVE_MEMORY_H 1
+
+/* Define to 1 if you have the <netinet/in.h> header file. */
+#define HAVE_NETINET_IN_H 1
+
+/* Define to 1 if you have the <ntdef.h> header file. */
+/* #undef HAVE_NTDEF_H */
+
+/* Define to 1 if you have the <ntstatus.h> header file. */
+/* #undef HAVE_NTSTATUS_H */
+
+/* use O_NONBLOCK for non-blocking sockets */
+#define HAVE_O_NONBLOCK 1
+
+/* Define to 1 if you have the `poll' function. */
+/* #undef HAVE_POLL */
+
+/* Define to 1 if you have the select function. */
+#define HAVE_SELECT 1
+
+/* use SO_NONBLOCK for non-blocking sockets */
+/* #undef HAVE_SO_NONBLOCK */
+
+/* Define to 1 if you have the <stdint.h> header file. */
+#define HAVE_STDINT_H 1
+
+/* Define to 1 if you have the <stdio.h> header file. */
+#define HAVE_STDIO_H 1
+
+/* Define to 1 if you have the <stdlib.h> header file. */
+#define HAVE_STDLIB_H 1
+
+/* Define to 1 if you have the <strings.h> header file. */
+#define HAVE_STRINGS_H 1
+
+/* Define to 1 if you have the <string.h> header file. */
+#define HAVE_STRING_H 1
+
+/* Define to 1 if you have the `strtoll' function. */
+#define HAVE_STRTOLL 1
+
+/* Define to 1 if you have the <sys/ioctl.h> header file. */
+#define HAVE_SYS_IOCTL_H 1
+
+/* Define to 1 if you have the <sys/select.h> header file. */
+#define HAVE_SYS_SELECT_H 1
+
+/* Define to 1 if you have the <sys/socket.h> header file. */
+#define HAVE_SYS_SOCKET_H 1
+
+/* Define to 1 if you have the <sys/stat.h> header file. */
+#define HAVE_SYS_STAT_H 1
+
+/* Define to 1 if you have the <sys/time.h> header file. */
+#define HAVE_SYS_TIME_H 1
+
+/* Define to 1 if you have the <sys/types.h> header file. */
+#define HAVE_SYS_TYPES_H 1
+
+/* Define to 1 if you have the <sys/uio.h> header file. */
+#define HAVE_SYS_UIO_H 1
+
+/* Define to 1 if you have the <sys/un.h> header file. */
+#define HAVE_SYS_UN_H 1
+
+/* Define to 1 if you have the <unistd.h> header file. */
+#define HAVE_UNISTD_H 1
+
+/* Define to 1 if you have the <windows.h> header file. */
+/* #undef HAVE_WINDOWS_H */
+
+/* Define to 1 if you have the <winsock2.h> header file. */
+/* #undef HAVE_WINSOCK2_H */
+
+/* Define to 1 if you have the <ws2tcpip.h> header file. */
+/* #undef HAVE_WS2TCPIP_H */
+
+/* to make a symbol visible */
+/* #undef LIBSSH2_API */
+
+/* Enable clearing of memory before being freed */
+/* #undef LIBSSH2_CLEAR_MEMORY */
+
+/* Enable "none" cipher -- NOT RECOMMENDED */
+/* #undef LIBSSH2_CRYPT_NONE */
+
+/* Enable newer diffie-hellman-group-exchange-sha1 syntax */
+#define LIBSSH2_DH_GEX_NEW 1
+
+/* Compile in zlib support */
+#define LIBSSH2_HAVE_ZLIB 1
+
+/* Use libgcrypt */
+/* #undef LIBSSH2_LIBGCRYPT */
+
+/* Enable "none" MAC -- NOT RECOMMENDED */
+/* #undef LIBSSH2_MAC_NONE */
+
+/* Use mbedtls */
+/* #undef LIBSSH2_MBEDTLS */
+
+/* Use OpenSSL */
+#define LIBSSH2_OPENSSL 1
+
+/* Use Windows CNG */
+/* #undef LIBSSH2_WINCNG */
+
+/* Define to the sub-directory where libtool stores uninstalled libraries. */
+#define LT_OBJDIR ".libs/"
+
+/* Define to 1 if _REENTRANT preprocessor symbol must be defined. */
+/* #undef NEED_REENTRANT */
+
+/* Name of package */
+#define PACKAGE "libssh2"
+
+/* Define to the address where bug reports for this package should be sent. */
+#define PACKAGE_BUGREPORT "libssh2-devel@cool.haxx.se"
+
+/* Define to the full name of this package. */
+#define PACKAGE_NAME "libssh2"
+
+/* Define to the full name and version of this package. */
+#define PACKAGE_STRING "libssh2 -"
+
+/* Define to the one symbol short name of this package. */
+#define PACKAGE_TARNAME "libssh2"
+
+/* Define to the home page for this package. */
+#define PACKAGE_URL ""
+
+/* Define to the version of this package. */
+#define PACKAGE_VERSION "-"
+
+/* If using the C implementation of alloca, define if you know the
+   direction of stack growth for your system; otherwise it will be
+   automatically deduced at runtime.
+	STACK_DIRECTION > 0 => grows toward higher addresses
+	STACK_DIRECTION < 0 => grows toward lower addresses
+	STACK_DIRECTION = 0 => direction of growth unknown */
+/* #undef STACK_DIRECTION */
+
+/* Define to 1 if you have the ANSI C header files. */
+#define STDC_HEADERS 1
+
+/* Version number of package */
+#define VERSION "-"
+
+/* Define WORDS_BIGENDIAN to 1 if your processor stores words with the most
+   significant byte first (like Motorola and SPARC, unlike Intel). */
+#if defined AC_APPLE_UNIVERSAL_BUILD
+# if defined __BIG_ENDIAN__
+#  define WORDS_BIGENDIAN 1
+# endif
+#else
+# ifndef WORDS_BIGENDIAN
+/* #  undef WORDS_BIGENDIAN */
+# endif
+#endif
+
+/* Enable large inode numbers on Mac OS X 10.5.  */
+#ifndef _DARWIN_USE_64_BIT_INODE
+# define _DARWIN_USE_64_BIT_INODE 1
+#endif
+
+/* Number of bits in a file offset, on hosts where this is settable. */
+/* #undef _FILE_OFFSET_BITS */
+
+/* Define for large files, on AIX-style hosts. */
+/* #undef _LARGE_FILES */
+
+/* Define to empty if `const' does not conform to ANSI C. */
+/* #undef const */
+
+/* Define to `__inline__' or `__inline' if that's what the C compiler
+   calls it, or to nothing if 'inline' is not supported under any name.  */
+#ifndef __cplusplus
+/* #undef inline */
+#endif
+
+/* Define to `unsigned int' if <sys/types.h> does not define. */
+/* #undef size_t */
diff --git a/vendor/static_config/libssh2/win32/libssh2_config.h b/vendor/static_config/libssh2/win32/libssh2_config.h
new file mode 100644
index 000000000..b6af97806
--- /dev/null
+++ b/vendor/static_config/libssh2/win32/libssh2_config.h
@@ -0,0 +1,46 @@
+#ifndef LIBSSH2_CONFIG_H
+#define LIBSSH2_CONFIG_H
+
+#ifndef WIN32
+#define WIN32
+#endif
+#ifndef _CRT_SECURE_NO_DEPRECATE
+#define _CRT_SECURE_NO_DEPRECATE 1
+#endif /* _CRT_SECURE_NO_DEPRECATE */
+#include <winsock2.h>
+#include <mswsock.h>
+#include <ws2tcpip.h>
+
+#ifdef __MINGW32__
+#define HAVE_UNISTD_H
+#define HAVE_INTTYPES_H
+#define HAVE_SYS_TIME_H
+#define HAVE_GETTIMEOFDAY
+#endif /* __MINGW32__ */
+
+#define LIBSSH2_OPENSSL
+#define HAVE_WINSOCK2_H
+#define HAVE_IOCTLSOCKET
+#define HAVE_SELECT
+
+#ifdef _MSC_VER
+#if _MSC_VER < 1900
+#define snprintf _snprintf
+#if _MSC_VER < 1500
+#define vsnprintf _vsnprintf
+#endif
+#define strdup _strdup
+#define strncasecmp _strnicmp
+#define strcasecmp _stricmp
+#endif
+#else
+#ifndef __MINGW32__
+#define strncasecmp strnicmp
+#define strcasecmp stricmp
+#endif /* __MINGW32__ */
+#endif /* _MSC_VER */
+
+/* Enable newer diffie-hellman-group-exchange-sha1 syntax */
+#define LIBSSH2_DH_GEX_NEW 1
+
+#endif /* LIBSSH2_CONFIG_H */
diff --git a/vendor/openssl_distributions.json b/vendor/static_config/openssl_distributions.json
similarity index 100%
rename from vendor/openssl_distributions.json
rename to vendor/static_config/openssl_distributions.json