diff --git a/src/cmake/Modules/CheckMSize.cc b/src/cmake/Modules/CheckMSize.cc
index 6429709a3..b4ea27a8a 100644
--- a/src/cmake/Modules/CheckMSize.cc
+++ b/src/cmake/Modules/CheckMSize.cc
@@ -15,11 +15,11 @@ int main() {
     for (unsigned i = 1; i < MAX_SZ; i++) {
         void * p = malloc(i);
         size_t r = _msize(p);
-        if (r < i || r > 2*(i + 8)) {
-            fprintf(stderr, "Unexpected _msize behavior");
-            return 0;
+        if (r < i || ((i > 128) && (r > 2 * i))) {
+            fprintf(stderr, "Unexpected _msize behavior: i = %d, r = %d\n", i, int(r));
+            return 1;
         }
         free(p);
     }
-    return 1;
+    return 0;
 }
diff --git a/src/cmake/Modules/CheckMallocUsableSize.cc b/src/cmake/Modules/CheckMallocUsableSize.cc
index 9a0e28a61..04e28040c 100644
--- a/src/cmake/Modules/CheckMallocUsableSize.cc
+++ b/src/cmake/Modules/CheckMallocUsableSize.cc
@@ -15,11 +15,11 @@ int main() {
     for (unsigned i = 1; i < MAX_SZ; i++) {
         void * p = malloc(i);
         size_t r = malloc_usable_size(p);
-        if (r < i || r > 2*(i + 8)) {
-            fprintf(stderr, "Unexpected malloc_usable_size behavior");
-            return 0;
+        if (r < i || ((i > 128) && (r > 2 * i))) {
+            fprintf(stderr, "Unexpected malloc_usable_size behavior: i = %d, r = %d\n", i, int(r));
+            return 1;
         }
         free(p);
     }
-    return 1;
+    return 0;
 }
diff --git a/src/cmake/Modules/FindMSize.cmake b/src/cmake/Modules/FindMSize.cmake
index 903210e45..3fa412f0c 100644
--- a/src/cmake/Modules/FindMSize.cmake
+++ b/src/cmake/Modules/FindMSize.cmake
@@ -1,17 +1,46 @@
 find_path(MALLOC_DIR NAMES malloc.h )
 
-try_run(MSIZE_CHECK MSIZE_CHECK_BUILD
-  ${LEAN_BINARY_DIR}${CMAKE_FILES_DIRECTORY}/CMakeTmp
-  ${LEAN_SOURCE_DIR}/cmake/Modules/CheckMSize.cc
-  CMAKE_FLAGS -DINCLUDE_DIRECTORIES=${MALLOC_DIR}
-  RUN_OUTPUT_VARIABLE MSIZE_TRY_OUT)
-
-if("${MSIZE_CHECK_BUILD}" MATCHES "TRUE" AND "${MSIZE_CHECK}" MATCHES "0")
-  message(STATUS "Found malloc_usable_size")
-  set(MSIZE_FOUND TRUE)
+if(CMAKE_CROSSCOMPILING)
+  if("${CMAKE_SYSTEM_NAME}" MATCHES "Windows")
+    # If it's cross-compilation and target is windows, first compile MSIZE_CHECK.exe
+    execute_process(COMMAND ${CMAKE_CXX_COMPILER}
+      "-o" ${LEAN_BINARY_DIR}${CMAKE_FILES_DIRECTORY}/CMakeTmp/MSIZE_CHECK.exe
+      ${LEAN_SOURCE_DIR}/cmake/Modules/CheckMSize.cc
+      RESULT_VARIABLE MSIZE_CHECK_BUILD_RESULT)
+    if("${MSIZE_CHECK_BUILD_RESULT}" MATCHES "0")
+      set(MSIZE_CHECK_BUILD "TRUE")
+      # Check whether "wine" exists to run "MSIZE_CHECK.exe"
+      execute_process(COMMAND "bash" "-c" "wine --version > /dev/null 2&>1"
+                      RESULT_VARIABLE WINE_CHECK)
+      if("${WINE_CHECK}" MATCHES "0")
+        execute_process(COMMAND "wine"
+          ${LEAN_BINARY_DIR}${CMAKE_FILES_DIRECTORY}/CMakeTmp/MSIZE_CHECK.exe
+          RESULT_VARIABLE MSIZE_CHECK)
+      else()
+        # NOTE: We can compile a progrm with _msize, but we can't test
+        # it due to the lack of wine. We assume that it is usable
+        set(MSIZE_CHECK "0")
+        set(MSIZE_UNTESTED "(untested)")
+      endif()
+    else()
+      set(MSIZE_CHECK_BUILD "FALSE")
+    endif()
+  else()
+    # It's cross-compilation but the target is not Windows
+    set(MSIZE_FOUND FALSE)
+  endif()
 else()
-  message(STATUS "Usable malloc_usable_size was not detected")
-  set(MSIZE_FOUND FALSE)
+  try_run(MSIZE_CHECK MSIZE_CHECK_BUILD
+    ${LEAN_BINARY_DIR}${CMAKE_FILES_DIRECTORY}/CMakeTmp
+    ${LEAN_SOURCE_DIR}/cmake/Modules/CheckMSize.cc
+    CMAKE_FLAGS -DINCLUDE_DIRECTORIES=${MALLOC_DIR}
+    RUN_OUTPUT_VARIABLE MSIZE_TRY_OUT)
 endif()
 
-
+if("${MSIZE_CHECK_BUILD}" MATCHES "TRUE" AND "${MSIZE_CHECK}" MATCHES "0")
+  message(STATUS "Found _msize " "${MSIZE_UNTESTED}")
+  set(MSIZE_FOUND TRUE)
+else()
+  message(STATUS "Usable _msize was not detected")
+  set(MSIZE_FOUND FALSE)
+endif()