diff --git a/test/simple-memory-corruption/Makefile b/test/simple-memory-corruption/Makefile
index 4072f0c..e3cf7e1 100644
--- a/test/simple-memory-corruption/Makefile
+++ b/test/simple-memory-corruption/Makefile
@@ -1,6 +1,8 @@
 EXECUTABLES := \
     double_free_large \
+    double_free_large_delayed \
     double_free_small \
+    double_free_small_delayed \
     unaligned_free_large \
     unaligned_free_small \
     read_after_free_large \
diff --git a/test/simple-memory-corruption/double_free_large_delayed.c b/test/simple-memory-corruption/double_free_large_delayed.c
new file mode 100644
index 0000000..b448ea9
--- /dev/null
+++ b/test/simple-memory-corruption/double_free_large_delayed.c
@@ -0,0 +1,17 @@
+#include <stdlib.h>
+
+__attribute__((optimize(0)))
+int main(void) {
+    void *p = malloc(128 * 1024);
+    if (!p) {
+        return 1;
+    }
+    void *q = malloc(128 * 1024);
+    if (!q) {
+        return 1;
+    }
+    free(p);
+    free(q);
+    free(p);
+    return 0;
+}
diff --git a/test/simple-memory-corruption/double_free_small_delayed.c b/test/simple-memory-corruption/double_free_small_delayed.c
new file mode 100644
index 0000000..63d8586
--- /dev/null
+++ b/test/simple-memory-corruption/double_free_small_delayed.c
@@ -0,0 +1,17 @@
+#include <stdlib.h>
+
+__attribute__((optimize(0)))
+int main(void) {
+    void *p = malloc(16);
+    if (!p) {
+        return 1;
+    }
+    void *q = malloc(16);
+    if (!q) {
+        return 1;
+    }
+    free(p);
+    free(q);
+    free(p);
+    return 0;
+}