diff --git a/CMakeLists.txt b/CMakeLists.txt
index 828ee4227fc..14595e1ee5d 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -496,15 +496,15 @@ set(HERMES_LIT_TEST_PARAMS
   use_flowparser=${HERMES_USE_FLOWPARSER}
   jit_enabled=${HERMESVM_JIT}
   jit_disassembler_enabled=${HERMESVM_JIT_DISASSEMBLER}
-  hbc_deltaprep=${HERMES_BINARY_DIR}/bin/hbc-deltaprep
-  FileCheck=${LLVM_BUILD_DIR}/bin/FileCheck
-  hermes=${HERMES_BINARY_DIR}/bin/hermes
-  hermesc=${HERMES_BINARY_DIR}/bin/hermesc
-  hdb=${HERMES_BINARY_DIR}/bin/hdb
-  hbcdump=${HERMES_BINARY_DIR}/bin/hbcdump
-  repl=${HERMES_BINARY_DIR}/bin/hermes-repl
-  hbc-deltaprep=${HERMES_BINARY_DIR}/bin/hbc-deltaprep
-  hbc_diff=${HERMES_BINARY_DIR}/bin/hbc-diff
+  hbc_deltaprep=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hbc-deltaprep
+  FileCheck=${LLVM_BUILD_DIR}/${CMAKE_CFG_INTDIR}/bin/FileCheck
+  hermes=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hermes
+  hermesc=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hermesc
+  hdb=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hdb
+  hbcdump=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hbcdump
+  repl=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hermes-repl
+  hbc-deltaprep=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hbc-deltaprep
+  hbc_diff=${HERMES_BINARY_DIR}/${CMAKE_CFG_INTDIR}/bin/hbc-diff
   build_mode=${HERMES_ASSUMED_BUILD_MODE_IN_LIT_TEST}
   exception_on_oom_enabled=${HERMESVM_EXCEPTION_ON_OOM}
   serialize_enabled=${HERMESVM_SERIALIZE}
diff --git a/test/Driver/driver-test.sh b/test/Driver/driver-test.sh
index 92aa3bb20a1..d9e1baa36f4 100644
--- a/test/Driver/driver-test.sh
+++ b/test/Driver/driver-test.sh
@@ -5,6 +5,8 @@
 
 # RUN: sh %s %S %T %hermes
 # RUN: sh %s %S %T %hermesc
+# TODO(T53144040) Fix LIT tests on Windows
+# XFAIL: windows
 # shellcheck disable=SC2148
 
 SRCDIR=$1
diff --git a/test/Optimizer/cjs/cjs-static-fail-1.js b/test/Optimizer/cjs/cjs-static-fail-1.js
index 33f7ef93af8..343a0fd2fd3 100644
--- a/test/Optimizer/cjs/cjs-static-fail-1.js
+++ b/test/Optimizer/cjs/cjs-static-fail-1.js
@@ -4,55 +4,57 @@
 // file in the root directory of this source tree.
 //
 // RUN: %hermesc -fstatic-require -commonjs -emit-binary %s 2>&1 > /dev/null | %FileCheck --match-full-lines %s
+// TODO(T53144040) Fix LIT tests on Windows
+// XFAIL: windows
 
 foo(require);
-//CHECK: {{.*}}cjs-static-fail-1.js:8:4: warning: 'require' used as function call argument
+//CHECK: {{.*}}cjs-static-fail-1.js:10:4: warning: 'require' used as function call argument
 //CHECK-NEXT: foo(require);
 //CHECK-NEXT:    ^
 
 require(require);
-//CHECK: {{.*}}cjs-static-fail-1.js:13:8: warning: 'require' used as function call argument
+//CHECK: {{.*}}cjs-static-fail-1.js:15:8: warning: 'require' used as function call argument
 //CHECK-NEXT: require(require);
 //CHECK-NEXT:        ^
 
 new require("a");
-//CHECK: {{.*}}cjs-static-fail-1.js:18:12: warning: 'require' used as a constructor
+//CHECK: {{.*}}cjs-static-fail-1.js:20:12: warning: 'require' used as a constructor
 //CHECK-NEXT: new require("a");
 //CHECK-NEXT:            ^
 
 this.prop1 = require;
-//CHECK: {{.*}}cjs-static-fail-1.js:23:12: warning: 'require' escapes or is modified
+//CHECK: {{.*}}cjs-static-fail-1.js:25:12: warning: 'require' escapes or is modified
 //CHECK-NEXT: this.prop1 = require;
 //CHECK-NEXT:            ^
 
 require();
-//CHECK: {{.*}}cjs-static-fail-1.js:28:8: warning: require() invoked without arguments
+//CHECK: {{.*}}cjs-static-fail-1.js:30:8: warning: require() invoked without arguments
 //CHECK-NEXT: require();
 //CHECK-NEXT:        ^
 
 require("b", "c");
-//CHECK: {{.*}}cjs-static-fail-1.js:33:8: warning: Additional require() arguments will be ignored
+//CHECK: {{.*}}cjs-static-fail-1.js:35:8: warning: Additional require() arguments will be ignored
 //CHECK-NEXT: require("b", "c");
 //CHECK-NEXT:        ^
 
 require(foo + 1);
-//CHECK: {{.*}}cjs-static-fail-1.js:38:8: warning: require() argument cannot be coerced to constant string at compile time
+//CHECK: {{.*}}cjs-static-fail-1.js:40:8: warning: require() argument cannot be coerced to constant string at compile time
 //CHECK-NEXT: require(foo + 1);
 //CHECK-NEXT:        ^
-//CHECK: {{.*}}cjs-static-fail-1.js:38:9: note: First argument of require()
+//CHECK: {{.*}}cjs-static-fail-1.js:40:9: note: First argument of require()
 //CHECK-NEXT: require(foo + 1);
 //CHECK-NEXT:         ^
 
 function func() {
     require("c");
     var r = require;
-//CHECK: {{.*}}cjs-static-fail-1.js:48:11: warning: 'require' is copied to a variable which cannot be analyzed
+//CHECK: {{.*}}cjs-static-fail-1.js:50:11: warning: 'require' is copied to a variable which cannot be analyzed
 //CHECK-NEXT:     var r = require;
 //CHECK-NEXT:           ^
 }
 
 print({}[require]);
-//CHECK: {{.*}}cjs-static-fail-1.js:54:9: warning: 'require' is used as a property key and cannot be analyzed
+//CHECK: {{.*}}cjs-static-fail-1.js:56:9: warning: 'require' is used as a property key and cannot be analyzed
 //CHECK-NEXT: print({}[require]);
 //CHECK-NEXT:         ^
 
diff --git a/test/Optimizer/cjs/cjs-static-fail-2.js b/test/Optimizer/cjs/cjs-static-fail-2.js
index 20b70a8cae7..904f6f898a6 100644
--- a/test/Optimizer/cjs/cjs-static-fail-2.js
+++ b/test/Optimizer/cjs/cjs-static-fail-2.js
@@ -4,42 +4,44 @@
 // file in the root directory of this source tree.
 //
 // RUN: %hermesc -O -fstatic-require -commonjs -emit-binary %s 2>&1 > /dev/null | %FileCheck --match-full-lines %s
+// TODO(T53144040) Fix LIT tests on Windows
+// XFAIL: windows
 
 foo(require);
-//CHECK: {{.*}}cjs-static-fail-2.js:8:4: warning: 'require' used as function call argument
+//CHECK: {{.*}}cjs-static-fail-2.js:10:4: warning: 'require' used as function call argument
 //CHECK-NEXT: foo(require);
 //CHECK-NEXT:    ^
 
 require(require);
-//CHECK: {{.*}}cjs-static-fail-2.js:13:8: warning: 'require' used as function call argument
+//CHECK: {{.*}}cjs-static-fail-2.js:15:8: warning: 'require' used as function call argument
 //CHECK-NEXT: require(require);
 //CHECK-NEXT:        ^
 
 new require("a");
-//CHECK: {{.*}}cjs-static-fail-2.js:18:12: warning: 'require' used as a constructor
+//CHECK: {{.*}}cjs-static-fail-2.js:20:12: warning: 'require' used as a constructor
 //CHECK-NEXT: new require("a");
 //CHECK-NEXT:            ^
 
 this.prop1 = require;
-//CHECK: {{.*}}cjs-static-fail-2.js:23:12: warning: 'require' escapes or is modified
+//CHECK: {{.*}}cjs-static-fail-2.js:25:12: warning: 'require' escapes or is modified
 //CHECK-NEXT: this.prop1 = require;
 //CHECK-NEXT:            ^
 
 require();
-//CHECK: {{.*}}cjs-static-fail-2.js:28:8: warning: require() invoked without arguments
+//CHECK: {{.*}}cjs-static-fail-2.js:30:8: warning: require() invoked without arguments
 //CHECK-NEXT: require();
 //CHECK-NEXT:        ^
 
 require("b", "c");
-//CHECK: {{.*}}cjs-static-fail-2.js:33:8: warning: Additional require() arguments will be ignored
+//CHECK: {{.*}}cjs-static-fail-2.js:35:8: warning: Additional require() arguments will be ignored
 //CHECK-NEXT: require("b", "c");
 //CHECK-NEXT:        ^
 
 require(foo + 1);
-//CHECK: {{.*}}cjs-static-fail-2.js:38:8: warning: require() argument cannot be coerced to constant string at compile time
+//CHECK: {{.*}}cjs-static-fail-2.js:40:8: warning: require() argument cannot be coerced to constant string at compile time
 //CHECK-NEXT: require(foo + 1);
 //CHECK-NEXT:        ^
-//CHECK: {{.*}}cjs-static-fail-2.js:38:9: note: First argument of require()
+//CHECK: {{.*}}cjs-static-fail-2.js:40:9: note: First argument of require()
 //CHECK-NEXT: require(foo + 1);
 //CHECK-NEXT:         ^
 
diff --git a/test/Optimizer/promotion_on_switch.js b/test/Optimizer/promotion_on_switch.js
index 781ffb49810..a1ce2f458cc 100644
--- a/test/Optimizer/promotion_on_switch.js
+++ b/test/Optimizer/promotion_on_switch.js
@@ -4,6 +4,8 @@
 // file in the root directory of this source tree.
 //
 // RUN: %hermes -target=HBC -emit-binary -O %s > /dev/null
+// TODO(T53144040) Fix LIT tests on Windows
+// XFAIL: windows
 
 function days_of_the_w_ek(x) {
   switch (1) {
diff --git a/test/hermes/date-locale.js b/test/hermes/date-locale.js
index fc7f2eecba6..7dd91042ba1 100644
--- a/test/hermes/date-locale.js
+++ b/test/hermes/date-locale.js
@@ -10,6 +10,8 @@ RUN: TZ=EST+5 LC_ALL=tr_TR _HERMES_TEST_LOCALE=tr_TR %hermes -O -target=HBC %s \
 RUN:            | %FileCheck --match-full-lines -check-prefix TR %s
 RUN: TZ=EST+5 %hermes -O -target=HBC %s \
 RUN:            | %FileCheck --match-full-lines -check-prefix NO %s
+TODO(T53144040) Fix LIT tests on Windows
+XFAIL: windows
 */
 "use strict";
 
diff --git a/test/hermes/string-locale.js b/test/hermes/string-locale.js
index 902263be4c0..0753c09bdc0 100644
--- a/test/hermes/string-locale.js
+++ b/test/hermes/string-locale.js
@@ -10,6 +10,8 @@ RUN: LC_ALL=tr_TR.UTF-8 _HERMES_TEST_LOCALE=tr_TR.UTF-8 %hermes -O -target=HBC %
 RUN:            | %FileCheck --match-full-lines -check-prefix TR %s
 RUN: LC_ALL=UTF-8 _HERMES_TEST_LOCALE=UTF-8 %hermes -O -target=HBC %s \
 RUN:            | %FileCheck --match-full-lines -check-prefix NO %s
+TODO(T53144040) Fix LIT tests on Windows
+XFAIL: windows
 */
 "use strict";
 
diff --git a/test/lit.cfg b/test/lit.cfg
index a367f728307..d0fa862feca 100644
--- a/test/lit.cfg
+++ b/test/lit.cfg
@@ -1,5 +1,6 @@
 import lit
 import os
+import sys
 
 def isTrue(v):
   """Check whether a string converts to True according to CMake rules"""
@@ -39,6 +40,12 @@ if lit_config.params["build_mode"] != "opt":
   if lit_config.params["build_mode"] == "dbg":
     config.available_features.add("slow_debug")
 
+if sys.platform.startswith('cygwin'):
+  lit_config.fatal('Running Hermes LIT tests in cygwin Python is not '
+      + 'supported. Please use regular Python on Windows.')
+if os.name == 'nt':
+  config.available_features.add("windows")
+
 # Note substitutions are applied in order.
 # %hermesc must appear before %hermes, or else %hermes will substitute *inside* %hermesc
 config.substitutions.append(("%FileCheck", lit_config.params["FileCheck"]))