diff --git a/contrib/devtools/symbol-check.py b/contrib/devtools/symbol-check.py
--- a/contrib/devtools/symbol-check.py
+++ b/contrib/devtools/symbol-check.py
@@ -216,6 +216,16 @@
     return ok
 
 
+def check_MACHO_min_os(filename) -> bool:
+    binary = lief.parse(filename)
+    return binary.build_version.minos == [10, 14, 0]
+
+
+def check_MACHO_sdk(filename) -> bool:
+    binary = lief.parse(filename)
+    return binary.build_version.sdk == [10, 15, 6]
+
+
 def check_PE_libraries(filename) -> bool:
     ok: bool = True
     binary = lief.parse(filename)
@@ -226,6 +236,13 @@
     return ok
 
 
+def check_PE_subsystem_version(filename) -> bool:
+    binary = lief.parse(filename)
+    major: int = binary.optional_header.major_subsystem_version
+    minor: int = binary.optional_header.minor_subsystem_version
+    return major == 6 and minor == 1
+
+
 CHECKS = {
     'ELF': [
         ('IMPORTED_SYMBOLS', check_imported_symbols),
@@ -233,10 +250,13 @@
         ('LIBRARY_DEPENDENCIES', check_ELF_libraries)
     ],
     'MACHO': [
-        ('DYNAMIC_LIBRARIES', check_MACHO_libraries)
+        ('DYNAMIC_LIBRARIES', check_MACHO_libraries),
+        ('MIN_OS', check_MACHO_min_os),
+        ('SDK', check_MACHO_sdk),
     ],
     'PE': [
-        ('DYNAMIC_LIBRARIES', check_PE_libraries)
+        ('DYNAMIC_LIBRARIES', check_PE_libraries),
+        ('SUBSYSTEM_VERSION', check_PE_subsystem_version),
     ]
 }
 
diff --git a/contrib/devtools/test-symbol-check.py b/contrib/devtools/test-symbol-check.py
--- a/contrib/devtools/test-symbol-check.py
+++ b/contrib/devtools/test-symbol-check.py
@@ -105,7 +105,7 @@
 
         self.assertEqual(call_symbol_check(cc, source, executable, ['-lexpat']),
                          (1, 'libexpat.1.dylib is not in ALLOWED_LIBRARIES!\n' +
-                          executable + ': failed DYNAMIC_LIBRARIES'))
+                          f'{executable}: failed DYNAMIC_LIBRARIES MIN_OS SDK'))
 
         source = 'test2.c'
         executable = 'test2'
@@ -120,8 +120,23 @@
                 }
         ''')
 
-        self.assertEqual(call_symbol_check(cc, source, executable, ['-framework', 'CoreGraphics']),
-                         (0, ''))
+        self.assertEqual(call_symbol_check(cc, source, executable,
+                                           ['-framework', 'CoreGraphics']),
+                         (1, f'{executable}: failed MIN_OS SDK'))
+
+        source = 'test3.c'
+        executable = 'test3'
+        with open(source, 'w', encoding="utf8") as f:
+            f.write('''
+                int main()
+                {
+                    return 0;
+                }
+        ''')
+
+        self.assertEqual(call_symbol_check(cc, source, executable,
+                                           ['-mmacosx-version-min=10.14']),
+                         (1, f'{executable}: failed SDK'))
 
     def test_PE(self):
         source = 'test1.c'
@@ -139,12 +154,30 @@
                 }
         ''')
 
-        self.assertEqual(call_symbol_check(cc, source, executable, ['-lpdh']),
-                         (1, 'pdh.dll is not in ALLOWED_LIBRARIES!\n' +
-                          executable + ': failed DYNAMIC_LIBRARIES'))
+        self.assertEqual(
+            call_symbol_check(
+                cc, source, executable,
+                ['-lpdh', '-Wl,--major-subsystem-version', '-Wl,6',
+                 '-Wl,--minor-subsystem-version', '-Wl,1']),
+            (1, 'pdh.dll is not in ALLOWED_LIBRARIES!\n' +
+             executable + ': failed DYNAMIC_LIBRARIES'))
 
         source = 'test2.c'
         executable = 'test2.exe'
+
+        with open(source, 'w', encoding="utf8") as f:
+            f.write('''
+                int main()
+                {
+                    return 0;
+                }
+        ''')
+
+        self.assertEqual(call_symbol_check(cc, source, executable, ['-Wl,--major-subsystem-version', '-Wl,9', '-Wl,--minor-subsystem-version', '-Wl,9']),
+                         (1, executable + ': failed SUBSYSTEM_VERSION'))
+
+        source = 'test3.c'
+        executable = 'test3.exe'
         with open(source, 'w', encoding="utf8") as f:
             f.write('''
                 #include <windows.h>
@@ -156,8 +189,11 @@
                 }
         ''')
 
-        self.assertEqual(call_symbol_check(cc, source, executable, ['-lole32']),
-                         (0, ''))
+        self.assertEqual(
+            call_symbol_check(cc, source, executable,
+                              ['-lole32', '-Wl,--major-subsystem-version', '-Wl,6',
+                               '-Wl,--minor-subsystem-version', '-Wl,1']),
+            (0, ''))
 
 
 if __name__ == '__main__':
diff --git a/contrib/gitian-descriptors/gitian-linux.yml b/contrib/gitian-descriptors/gitian-linux.yml
--- a/contrib/gitian-descriptors/gitian-linux.yml
+++ b/contrib/gitian-descriptors/gitian-linux.yml
@@ -118,7 +118,7 @@
   done
   }
 
-  pip3 install lief==0.11.4
+  pip3 install lief==0.11.5
 
   # Faketime for depends so intermediate results are comparable
   export PATH_orig=${PATH}
diff --git a/contrib/gitian-descriptors/gitian-osx.yml b/contrib/gitian-descriptors/gitian-osx.yml
--- a/contrib/gitian-descriptors/gitian-osx.yml
+++ b/contrib/gitian-descriptors/gitian-osx.yml
@@ -87,7 +87,7 @@
   done
   }
 
-  pip3 install lief==0.11.4
+  pip3 install lief==0.11.5
 
   # Faketime for depends so intermediate results are comparable
   export PATH_orig=${PATH}
diff --git a/contrib/gitian-descriptors/gitian-win.yml b/contrib/gitian-descriptors/gitian-win.yml
--- a/contrib/gitian-descriptors/gitian-win.yml
+++ b/contrib/gitian-descriptors/gitian-win.yml
@@ -95,7 +95,7 @@
   done
   }
 
-  pip3 install lief==0.11.4
+  pip3 install lief==0.11.5
 
   # Faketime for depends so intermediate results are comparable
   export PATH_orig=${PATH}