diff --git a/src/checkout.c b/src/checkout.c
index de48c9e01..8c06b3335 100644
--- a/src/checkout.c
+++ b/src/checkout.c
@@ -243,6 +243,12 @@ static int checkout_action_common(
 		if (delta->new_file.mode == GIT_FILEMODE_LINK && wd != NULL)
 			*action |= CHECKOUT_ACTION__REMOVE;
 
+		/* if the file is on disk and doesn't match our mode, force update */
+		if (wd &&
+			GIT_PERMS_IS_EXEC(wd->mode) !=
+			GIT_PERMS_IS_EXEC(delta->new_file.mode))
+				*action |= CHECKOUT_ACTION__REMOVE;
+
 		notify = GIT_CHECKOUT_NOTIFY_UPDATED;
 	}
 
@@ -1500,15 +1506,6 @@ static int blob_content_to_file(
 	if (error < 0)
 		return error;
 
-	if (GIT_PERMS_IS_EXEC(mode)) {
-		data->perfdata.chmod_calls++;
-
-		if ((error = p_chmod(path, mode)) < 0) {
-			giterr_set(GITERR_OS, "Failed to set permissions on '%s'", path);
-			return error;
-		}
-	}
-
 	if (st) {
 		data->perfdata.stat_calls++;
 
diff --git a/tests/checkout/tree.c b/tests/checkout/tree.c
index 5692e1f25..5680b86df 100644
--- a/tests/checkout/tree.c
+++ b/tests/checkout/tree.c
@@ -996,7 +996,8 @@ mode_t read_filemode(const char *path)
 	git_buf_joinpath(&fullpath, "testrepo", path);
 	cl_must_pass(p_stat(fullpath.ptr, &st));
 
-	result = GIT_PERMS_IS_EXEC(st.st_mode) ? 0100755 : 0100644;
+	result = GIT_PERMS_IS_EXEC(st.st_mode) ?
+		GIT_FILEMODE_BLOB_EXECUTABLE : GIT_FILEMODE_BLOB;
 
 	git_buf_free(&fullpath);