diff --git a/test/addons/openssl-binding/binding.gyp b/test/addons/openssl-binding/binding.gyp
index 672f84bb860..bafde41348c 100644
--- a/test/addons/openssl-binding/binding.gyp
+++ b/test/addons/openssl-binding/binding.gyp
@@ -2,8 +2,12 @@
   'targets': [
     {
       'target_name': 'binding',
-      'sources': ['binding.cc'],
-      'include_dirs': ['../../../deps/openssl/openssl/include'],
+      'conditions': [
+         ['node_use_openssl=="true"', {
+           'sources': ['binding.cc'],
+           'include_dirs': ['../../../deps/openssl/openssl/include'],
+         }]
+      ]
     },
   ]
 }
diff --git a/test/addons/openssl-binding/test.js b/test/addons/openssl-binding/test.js
index a146ffe5c68..452f59f752f 100644
--- a/test/addons/openssl-binding/test.js
+++ b/test/addons/openssl-binding/test.js
@@ -1,6 +1,10 @@
 'use strict';
 
 const common = require('../../common');
+if (!common.hasCrypto) {
+  common.skip('missing crypto');
+  process.exit(0);
+}
 const assert = require('assert');
 const binding = require(`./build/${common.buildType}/binding`);
 const bytes = new Uint8Array(1024);
diff --git a/test/common.js b/test/common.js
index 6c7ea387e38..9f73e2e8820 100644
--- a/test/common.js
+++ b/test/common.js
@@ -638,3 +638,10 @@ exports.expectsError = function expectsError({code, type, message}) {
     return true;
   };
 };
+
+exports.skipIfInspectorDisabled = function skipIfInspectorDisabled() {
+  if (!exports.hasCrypto) {
+    exports.skip('missing ssl support so inspector is disabled');
+    process.exit(0);
+  }
+};
diff --git a/test/fixtures/tls-connect.js b/test/fixtures/tls-connect.js
index 72f83736bf3..a434a0316d6 100644
--- a/test/fixtures/tls-connect.js
+++ b/test/fixtures/tls-connect.js
@@ -6,19 +6,15 @@
 const common = require('../common');
 const fs = require('fs');
 const join = require('path').join;
+// Check if Node was compiled --without-ssl and if so exit early
+// as the require of tls will otherwise throw an Error.
+if (!common.hasCrypto) {
+  common.skip('missing crypto');
+  process.exit(0);
+}
 const tls = require('tls');
 const util = require('util');
 
-module.exports = exports = checkCrypto;
-
-function checkCrypto() {
-  if (!common.hasCrypto) {
-    common.skip('missing crypto');
-    process.exit(0);
-  }
-  return exports;
-}
-
 exports.assert = require('assert');
 exports.debug = util.debuglog('test');
 exports.tls = tls;
diff --git a/test/inspector/test-inspector.js b/test/inspector/test-inspector.js
index a1c69cb6fbb..5cad934e7a5 100644
--- a/test/inspector/test-inspector.js
+++ b/test/inspector/test-inspector.js
@@ -1,5 +1,6 @@
 'use strict';
-require('../common');
+const common = require('../common');
+common.skipIfInspectorDisabled();
 const assert = require('assert');
 const helper = require('./inspector-helper.js');
 
diff --git a/test/inspector/test-not-blocked-on-idle.js b/test/inspector/test-not-blocked-on-idle.js
index 6d32888b44b..a33e530a548 100644
--- a/test/inspector/test-not-blocked-on-idle.js
+++ b/test/inspector/test-not-blocked-on-idle.js
@@ -1,5 +1,6 @@
 'use strict';
-require('../common');
+const common = require('../common');
+common.skipIfInspectorDisabled();
 const helper = require('./inspector-helper.js');
 
 function shouldShutDown(session) {
diff --git a/test/parallel/test-cluster-inspector-debug-port.js b/test/parallel/test-cluster-inspector-debug-port.js
index f2f8db9b5d5..f0e0f58a865 100644
--- a/test/parallel/test-cluster-inspector-debug-port.js
+++ b/test/parallel/test-cluster-inspector-debug-port.js
@@ -1,6 +1,7 @@
 'use strict';
 // Flags: --inspect={PORT}
 const common = require('../common');
+common.skipIfInspectorDisabled();
 const assert = require('assert');
 const cluster = require('cluster');
 const debuggerPort = common.PORT;
diff --git a/test/parallel/test-tls-addca.js b/test/parallel/test-tls-addca.js
index 7a6f9a77516..f3f5e5b8dea 100644
--- a/test/parallel/test-tls-addca.js
+++ b/test/parallel/test-tls-addca.js
@@ -8,7 +8,7 @@ const common = require('../common');
 const join = require('path').join;
 const {
   assert, connect, keys, tls
-} = require(join(common.fixturesDir, 'tls-connect'))();
+} = require(join(common.fixturesDir, 'tls-connect'));
 
 const contextWithoutCert = tls.createSecureContext({});
 const contextWithCert = tls.createSecureContext({});
diff --git a/test/parallel/test-tls-ca-concat.js b/test/parallel/test-tls-ca-concat.js
index 65c837bed9d..0c1908049be 100644
--- a/test/parallel/test-tls-ca-concat.js
+++ b/test/parallel/test-tls-ca-concat.js
@@ -7,7 +7,7 @@ const common = require('../common');
 const join = require('path').join;
 const {
   assert, connect, keys
-} = require(join(common.fixturesDir, 'tls-connect'))();
+} = require(join(common.fixturesDir, 'tls-connect'));
 
 connect({
   client: {
diff --git a/test/parallel/test-tls-cert-chains-concat.js b/test/parallel/test-tls-cert-chains-concat.js
index d53edef8984..a90ed67997e 100644
--- a/test/parallel/test-tls-cert-chains-concat.js
+++ b/test/parallel/test-tls-cert-chains-concat.js
@@ -7,7 +7,7 @@ const common = require('../common');
 const join = require('path').join;
 const {
   assert, connect, debug, keys
-} = require(join(common.fixturesDir, 'tls-connect'))();
+} = require(join(common.fixturesDir, 'tls-connect'));
 
 // agent6-cert.pem includes cert for agent6 and ca3
 connect({
diff --git a/test/parallel/test-tls-cert-chains-in-ca.js b/test/parallel/test-tls-cert-chains-in-ca.js
index 3b4e78919fb..03fae36cb74 100644
--- a/test/parallel/test-tls-cert-chains-in-ca.js
+++ b/test/parallel/test-tls-cert-chains-in-ca.js
@@ -7,7 +7,7 @@ const common = require('../common');
 const join = require('path').join;
 const {
   assert, connect, debug, keys
-} = require(join(common.fixturesDir, 'tls-connect'))();
+} = require(join(common.fixturesDir, 'tls-connect'));
 
 
 // agent6-cert.pem includes cert for agent6 and ca3, split it apart and
diff --git a/test/parallel/test-tls-connect-secure-context.js b/test/parallel/test-tls-connect-secure-context.js
index d1552a62169..ef063c2ed3a 100644
--- a/test/parallel/test-tls-connect-secure-context.js
+++ b/test/parallel/test-tls-connect-secure-context.js
@@ -6,7 +6,7 @@ const common = require('../common');
 const join = require('path').join;
 const {
   assert, connect, keys, tls
-} = require(join(common.fixturesDir, 'tls-connect'))();
+} = require(join(common.fixturesDir, 'tls-connect'));
 
 connect({
   client: {
diff --git a/test/parallel/test-tls-peer-certificate.js b/test/parallel/test-tls-peer-certificate.js
index eb5be6dcb22..8c56e72af14 100644
--- a/test/parallel/test-tls-peer-certificate.js
+++ b/test/parallel/test-tls-peer-certificate.js
@@ -6,7 +6,7 @@ const common = require('../common');
 const join = require('path').join;
 const {
   assert, connect, debug, keys
-} = require(join(common.fixturesDir, 'tls-connect'))();
+} = require(join(common.fixturesDir, 'tls-connect'));
 
 connect({
   client: {rejectUnauthorized: false},
diff --git a/test/parallel/test-tls-socket-default-options.js b/test/parallel/test-tls-socket-default-options.js
index 24b7a5d34ec..edf16a6bffc 100644
--- a/test/parallel/test-tls-socket-default-options.js
+++ b/test/parallel/test-tls-socket-default-options.js
@@ -9,11 +9,6 @@ const {
   connect, keys, tls
 } = require(join(common.fixturesDir, 'tls-connect'));
 
-if (!common.hasCrypto) {
-  common.skip('missing crypto');
-  return;
-}
-
 test(undefined, (err) => {
   assert.strictEqual(err.message, 'unable to verify the first certificate');
 });
diff --git a/test/sequential/test-debugger-debug-brk.js b/test/sequential/test-debugger-debug-brk.js
index f04af4544f8..f5a69b91d6b 100644
--- a/test/sequential/test-debugger-debug-brk.js
+++ b/test/sequential/test-debugger-debug-brk.js
@@ -1,5 +1,6 @@
 'use strict';
 const common = require('../common');
+common.skipIfInspectorDisabled();
 const assert = require('assert');
 const spawn = require('child_process').spawn;
 
diff --git a/test/testpy/__init__.py b/test/testpy/__init__.py
index 367346f6e15..d7ec88992e2 100644
--- a/test/testpy/__init__.py
+++ b/test/testpy/__init__.py
@@ -29,6 +29,7 @@ import test
 import os
 from os.path import join, dirname, exists
 import re
+import ast
 
 
 FLAGS_PATTERN = re.compile(r"//\s+Flags:(.*)")
@@ -64,7 +65,18 @@ class SimpleTestCase(test.TestCase):
       # PORT should match the definition in test/common.js.
       env = { 'PORT': int(os.getenv('NODE_COMMON_PORT', '12346')) }
       env['PORT'] += self.thread_id * 100
-      result += flags_match.group(1).strip().format(**env).split()
+      flag = flags_match.group(1).strip().format(**env).split()
+      # The following block reads config.gypi to extract the v8_enable_inspector
+      # value. This is done to check if the inspector is disabled in which case
+      # the '--inspect' flag cannot be passed to the node process as it will
+      # cause node to exit and report the test as failed. The use case
+      # is currently when Node is configured --without-ssl and the tests should
+      # still be runnable but skip any tests that require ssl (which includes the
+      # inspector related tests).
+      if flag[0].startswith('--inspect') and self.context.v8_enable_inspector == 0:
+        print('Skipping as inspector is disabled')
+      else:
+        result += flag
     files_match = FILES_PATTERN.search(source);
     additional_files = []
     if files_match:
diff --git a/tools/test.py b/tools/test.py
index d6715937b60..deeb7aeffe2 100755
--- a/tools/test.py
+++ b/tools/test.py
@@ -43,6 +43,7 @@ import utils
 import multiprocessing
 import errno
 import copy
+import ast
 
 from os.path import join, dirname, abspath, basename, isdir, exists
 from datetime import datetime
@@ -867,7 +868,8 @@ class Context(object):
 
   def __init__(self, workspace, buildspace, verbose, vm, args, expect_fail,
                timeout, processor, suppress_dialogs,
-               store_unexpected_output, repeat, abort_on_timeout):
+               store_unexpected_output, repeat, abort_on_timeout,
+               v8_enable_inspector):
     self.workspace = workspace
     self.buildspace = buildspace
     self.verbose = verbose
@@ -880,6 +882,7 @@ class Context(object):
     self.store_unexpected_output = store_unexpected_output
     self.repeat = repeat
     self.abort_on_timeout = abort_on_timeout
+    self.v8_enable_inspector = v8_enable_inspector
 
   def GetVm(self, arch, mode):
     if arch == 'none':
@@ -912,6 +915,19 @@ def RunTestCases(cases_to_run, progress, tasks, flaky_tests_mode):
   progress = PROGRESS_INDICATORS[progress](cases_to_run, flaky_tests_mode)
   return progress.Run(tasks)
 
+def GetV8InspectorEnabledFlag():
+  # The following block reads config.gypi to extract the v8_enable_inspector
+  # value. This is done to check if the inspector is disabled in which case
+  # the '--inspect' flag cannot be passed to the node process as it will
+  # cause node to exit and report the test as failed. The use case
+  # is currently when Node is configured --without-ssl and the tests should
+  # still be runnable but skip any tests that require ssl (which includes the
+  # inspector related tests).
+  with open('config.gypi', 'r') as f:
+    s = f.read()
+    config_gypi = ast.literal_eval(s)
+    return config_gypi['variables']['v8_enable_inspector']
+
 
 # -------------------------------------------
 # --- T e s t   C o n f i g u r a t i o n ---
@@ -1587,7 +1603,8 @@ def Main():
                     options.suppress_dialogs,
                     options.store_unexpected_output,
                     options.repeat,
-                    options.abort_on_timeout)
+                    options.abort_on_timeout,
+                    GetV8InspectorEnabledFlag())
 
   # Get status for tests
   sections = [ ]