diff --git a/test/testpy/__init__.py b/test/testpy/__init__.py
index 27d7124bf2ed16..7ba9674d7d6e57 100644
--- a/test/testpy/__init__.py
+++ b/test/testpy/__init__.py
@@ -61,7 +61,7 @@ def GetCommand(self):
     source = open(self.file).read()
     flags_match = FLAGS_PATTERN.search(source)
     if flags_match:
-      flag = flags_match.group(1).strip().split()
+      flags = flags_match.group(1).strip().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
@@ -71,13 +71,17 @@ def GetCommand(self):
       # inspector related tests). Also, if there is no ssl support the options
       # '--use-bundled-ca' and '--use-openssl-ca' will also cause a similar
       # failure so such tests are also skipped.
-      if ('--inspect' in flag[0] or \
-          '--use-bundled-ca' in flag[0] or \
-          '--use-openssl-ca' in flag[0]) and \
-          self.context.v8_enable_inspector == 0:
-        print('Skipping as node was configured --without-ssl')
+      if (any(flag.startswith('--inspect') for flag in flags) and
+          not self.context.v8_enable_inspector):
+        print('Skipping as node was compiled without inspector support')
+      elif (('--use-bundled-ca' in flags or
+          '--use-openssl-ca' in flags or
+          '--tls-v1.0' in flags or
+          '--tls-v1.1' in flags) and
+          not self.context.node_has_crypto):
+        print('Skipping as node was compiled without crypto support')
       else:
-        result += flag
+        result += flags
     files_match = FILES_PATTERN.search(source);
     additional_files = []
     if files_match:
diff --git a/tools/test.py b/tools/test.py
index 3a464be61da1b3..67b8cb917e0db6 100755
--- a/tools/test.py
+++ b/tools/test.py
@@ -907,6 +907,7 @@ def __init__(self, workspace, buildspace, verbose, vm, args, expect_fail,
     self.repeat = repeat
     self.abort_on_timeout = abort_on_timeout
     self.v8_enable_inspector = True
+    self.node_has_crypto = True
 
   def GetVm(self, arch, mode):
     if arch == 'none':
@@ -1632,9 +1633,14 @@ def Main():
 
   # We want to skip the inspector tests if node was built without the inspector.
   has_inspector = Execute([vm,
-      "-p", "process.config.variables.v8_enable_inspector"], context)
-  if has_inspector.stdout.rstrip() == "0":
-      context.v8_enable_inspector = False
+      '-p', 'process.config.variables.v8_enable_inspector'], context)
+  if has_inspector.stdout.rstrip() == '0':
+    context.v8_enable_inspector = False
+
+  has_crypto = Execute([vm,
+      '-p', 'process.versions.openssl'], context)
+  if has_crypto.stdout.rstrip() == 'undefined':
+    context.node_has_crypto = False
 
   if options.cat:
     visited = set()