diff --git a/deps/openssl/openssl.gyp b/deps/openssl/openssl.gyp
index 0ca75156117da8..4609d83baabac1 100644
--- a/deps/openssl/openssl.gyp
+++ b/deps/openssl/openssl.gyp
@@ -21,7 +21,8 @@
         }, 'target_arch=="arm64" and OS=="win"', {
           # VC-WIN64-ARM inherits from VC-noCE-common that has no asms.
           'includes': ['./openssl_no_asm.gypi'],
-        }, 'gas_version >= "2.26" or nasm_version >= "2.11.8"', {
+        }, 'gas_version and v(gas_version) >= v("2.26") or '
+           'nasm_version and v(nasm_version) >= v("2.11.8")', {
            # Require AVX512IFMA supported. See
            # https://www.openssl.org/docs/man1.1.1/man3/OPENSSL_ia32cap.html
            # Currently crypto/poly1305/asm/poly1305-x86_64.pl requires AVX512IFMA.
diff --git a/deps/openssl/openssl.gypi b/deps/openssl/openssl.gypi
index d6d2589083bbce..af08a33c9c445b 100644
--- a/deps/openssl/openssl.gypi
+++ b/deps/openssl/openssl.gypi
@@ -1036,7 +1036,9 @@
     #
     'conditions': [
       ['(OS=="win" and MSVS_VERSION>="2012") or '
-       'llvm_version>="3.3" or xcode_version>="5.0" or gas_version>="2.23"', {
+       'llvm_version and v(llvm_version) >= v("3.3") or '
+        'gas_version and v(gas_version) >= v("2.23") or '
+        'xcode_version and v(xcode_version) >= v("5.0")', {
         'openssl_sources_x64_win_masm': [
           '<@(openssl_sources_asm_latest_x64_win_masm)',
           '<@(openssl_sources_common_x64_win_masm)',
diff --git a/tools/gyp/pylib/gyp/input.py b/tools/gyp/pylib/gyp/input.py
index 8ea869a267ef6a..6db204e4010284 100644
--- a/tools/gyp/pylib/gyp/input.py
+++ b/tools/gyp/pylib/gyp/input.py
@@ -19,6 +19,7 @@
 import threading
 import time
 import traceback
+from distutils.version import StrictVersion
 from gyp.common import GypError
 from gyp.common import OrderedSet
 
@@ -1088,7 +1089,8 @@ def EvalSingleCondition(
     else:
       ast_code = compile(cond_expr_expanded, '<string>', 'eval')
       cached_conditions_asts[cond_expr_expanded] = ast_code
-    if eval(ast_code, {'__builtins__': None}, variables):
+    env = {'__builtins__': None, 'v': StrictVersion}
+    if eval(ast_code, env, variables):
       return true_dict
     return false_dict
   except SyntaxError as e: