@@ -61,11 +61,11 @@
             "conditions": [
               ["node_root_dir.split('/')[-1].startswith('iojs')", {
                 "include_dirs": [
-                  "/usr/local/opt/openssl@1.1/include"
+                  "vendor/openssl/include"
                 ],
                 "libraries": [
-                  "/usr/local/opt/openssl@1.1/lib/libcrypto.a",
-                  "/usr/local/opt/openssl@1.1/lib/libssl.a"
+                  "<(module_root_dir)/vendor/openssl/lib/libcrypto.a",
+                  "<(module_root_dir)/vendor/openssl/lib/libssl.a"
                 ]
               }]
             ],
@@ -86,20 +86,10 @@
           "OS=='win'", {
             "conditions": [
               ["node_root_dir.split('\\\\')[-1].startswith('iojs')", {
-                "conditions": [
-                  ["target_arch == 'x64'", {
-                    "include_dirs": ["vendor/win/openssl/include64"],
-                    "libraries": [
-                      "<(module_root_dir)/vendor/win/openssl/lib64/libcryptoMT.lib",
-                      "<(module_root_dir)/vendor/win/openssl/lib64/libsslMT.lib"
-                    ]
-                  }, {
-                    "include_dirs": ["vendor/win/openssl/include"],
-                    "libraries": [
-                      "<(module_root_dir)/vendor/win/openssl/lib/libcryptoMT.lib",
-                      "<(module_root_dir)/vendor/win/openssl/lib/libsslMT.lib"
-                    ]
-                  }]
+                "include_dirs": ["vendor/openssl/include"],
+                "libraries": [
+                  "<(module_root_dir)/vendor/openssl/lib/libcrypto.lib",
+                  "<(module_root_dir)/vendor/openssl/lib/libssl.lib"
                 ]
               }]
             ],
 
@@ -6,13 +6,6 @@ var rooted = function (dir) {
   return escapedPathForShell;
 };
 
-var isWin64 = function() {
-  return process.platform === "win32" && (
-    process.arch === "x64" ||
-    process.env.hasOwnProperty("PROCESSOR_ARCHITEW6432")
-  );
-};
-
 module.exports = function retrieveExternalDependencies() {
   if (process.platform === "win32") {
     return Promise.resolve("");
@@ -23,22 +16,18 @@ module.exports = function retrieveExternalDependencies() {
     var opensslDir;
 
     if (process.platform === "darwin") {
-      opensslDir = "/usr/local/opt/openssl@1.1";
-    } else if (process.platform === "win32") {
-      opensslDir = path.join(process.cwd(), "vendor", "win", "openssl");
+      opensslDir = "vendor/openssl";
     }
 
     var newEnv = {};
     Object.keys(process.env).forEach(function(key) {
       newEnv[key] = process.env[key];
     });
 
-    const includeDirName = isWin64() ? "include64" : "include";
-
     var maybeLibsslPrefix = "";
     if (opensslDir) {
       newEnv.CPPFLAGS = newEnv.CPPFLAGS || "";
-      newEnv.CPPFLAGS += " -I" + path.join(opensslDir, includeDirName);
+      newEnv.CPPFLAGS += " -I" + path.join(opensslDir, "include");
       newEnv.CPPFLAGS = newEnv.CPPFLAGS.trim();
       maybeLibsslPrefix = ` --with-libssl-prefix=${opensslDir}`;
     }
 
@@ -60,6 +60,7 @@
     "mocha": "^5.2.0",
     "ramda": "^0.25.0",
     "request-promise-native": "^1.0.5",
+    "tar-fs": "^1.16.3",
     "walk": "^2.3.9"
   },
   "vendorDependencies": {
 
@@ -0,0 +1,90 @@
+const fs = require('fs');
+const fse = require('fs-extra');
+const path = require('path');
+const R = require('ramda');
+const request = require('request-promise-native');
+const stream = require('stream');
+const tar = require('tar-fs');
+const zlib = require('zlib');
+
+const vendorPath = path.resolve('..', 'vendor');
+const distrosFilePath = path.join(vendorPath, 'openssl_distributions.json');
+const extractPath = path.join(vendorPath, 'openssl');
+
+const getOSName = () => {
+  if (process.platform === 'win32') {
+    if (process.arch === "x64" || process.env.hasOwnProperty("PROCESSOR_ARCHITEW6432")) {
+      return 'win64';
+    } else {
+      return 'win32';
+    }
+  } else if (process.platform === 'darwin') {
+    return 'macOS';
+  } else {
+    // We only discover distros for Mac and Windows. We don't care about any other OS.
+    return 'unknown';
+  }
+}
+
+const getCompilerVersion = () => {
+  // TODO: Get actual compiler version. For now, just assume latest compiler for distros in openssl_distributions.js
+  const osName = getOSName();
+  if (osName === 'win32' || osName === 'win64') {
+    return 'vs15';
+  } else if (osName === 'macOS') {
+    return 'clang-9';
+  } else {
+    // We only discover distros for Mac and Windows. We don't care about any other OS.
+    return 'unknown';
+  }
+}
+
+const getIsDebug = () => true // TODO: Determine if we are GYPing in Debug
+
+const getMatchingDistributionName = () =>
+  `${getOSName()}-${getCompilerVersion()}-static${getIsDebug() ? '-debug' : ''}`;
+
+const getDistributionsConfig = () =>
+  fse.readFile(distrosFilePath, 'utf8')
+    .then(JSON.parse)
+
+const getDistrbutionURLFromConfig = (config) => {
+  const distName = getMatchingDistributionName();
+  const distURL = R.propOr(null, distName, config);
+
+  if (!distURL) {
+    return Promise.reject(new Error('No matching distribution for this operating system'));
+  }
+  return Promise.resolve(distURL);
+}
+
+const fetchFileFromURL = (distUrl) => request({
+  method: 'GET',
+  uri: distUrl,
+  encoding: null,
+  gzip: true
+});
+
+const extractFile = (body) => new Promise((resolve, reject) => {
+  const streamableBody = new stream.Readable();
+  streamableBody.push(body);
+  streamableBody.push(null);
+  streamableBody
+    .pipe(zlib.createGunzip())
+    .on('error', reject)
+    .pipe(tar.extract(extractPath))
+    .on('error', reject)
+    .on('close', resolve);
+});
+
+const acquireOpenSSL = () =>
+  getDistributionsConfig()
+    .then(getDistrbutionURLFromConfig)
+    .then(fetchFileFromURL)
+    .then(extractFile)
+    .catch((e) => {
+      console.error(e);
+      process.exit(1);
+    });
+
+acquireOpenSSL();
@@ -363,13 +363,7 @@
                 },
               }],
               ["node_root_dir.split('\\\\')[-1].startswith('iojs')", {
-                "conditions": [
-                  ["target_arch=='x64'", {
-                    "include_dirs": ["win/openssl/include64"]
-                  }, {
-                    "include_dirs": ["win/openssl/include"]
-                  }]
-                ]
+                "include_dirs": ["openssl/include"]
               }]
             ],
           },
@@ -542,18 +536,14 @@
       "conditions": [
         ["OS=='mac' and node_root_dir.split('/')[-1].startswith('iojs')", {
           "include_dirs": [
-            "/usr/local/opt/openssl@1.1/include"
+            "openssl/include"
           ]
         }],
         ["OS=='win'", {
           "conditions": [
             ["node_root_dir.split('\\\\')[-1].startswith('iojs')", {
-              "conditions": [
-                ["target_arch=='x64'", {
-                  "include_dirs": ["win/openssl/include64"]
-                }, {
-                  "include_dirs": ["win/openssl/include"]
-                }]
+              "include_dirs": [
+                "openssl/include"
               ]
             }, {
               "defines": [