diff --git a/frontend/src/crypt.c b/frontend/src/crypt.c
index a376c46..1845b55 100644
--- a/frontend/src/crypt.c
+++ b/frontend/src/crypt.c
@@ -226,10 +226,7 @@ int encrypt(const char *const passphrase, const CHR *const input_path, const CHR
 
 clean_up:
 
-	if (ctx)
-	{
-		slunkcrypt_free(ctx);
-	}
+	SLUNKCRYPT_SAFE_FREE(ctx);
 
 	if (file_out)
 	{
@@ -424,10 +421,7 @@ int decrypt(const char *const passphrase, const CHR *const input_path, const CHR
 
 clean_up:
 
-	if (ctx)
-	{
-		slunkcrypt_free(ctx);
-	}
+	SLUNKCRYPT_SAFE_FREE(ctx);
 
 	if (file_out)
 	{
diff --git a/frontend/src/selftest.c b/frontend/src/selftest.c
index c21e9fe..cefe7bb 100644
--- a/frontend/src/selftest.c
+++ b/frontend/src/selftest.c
@@ -106,10 +106,7 @@ static int run_testcase(const char* const message, const uint64_t nonce, const u
 
 clean_up:
 
-	if (ctx)
-	{
-		slunkcrypt_free(ctx);
-	}
+	SLUNKCRYPT_SAFE_FREE(ctx);
 
 	if (text_temp)
 	{
@@ -120,9 +117,93 @@ clean_up:
 	return result;
 }
 
+static int run_stresstest(const uint64_t nonce)
+{
+	static const char* const TEST_PASSPHRASE = "OrpheanBeh0lderScry!Doubt";
+	static const size_t LENGTH = 134217689U, CHUNKZ_ENC = 8191U, CHUNKZ_DEC = 8179U;
+
+	int status, result = EXIT_FAILURE;
+	size_t offset, chunk_size;
+	slunkcrypt_t ctx = SLUNKCRYPT_NULL;
+
+	uint8_t* const buffer = (uint8_t*)malloc(LENGTH * sizeof(uint8_t));
+	if (!buffer)
+	{
+		FPUTS(T("\n\nWhoops: Failed to allocate message buffer!\n\n"), stderr);
+		goto clean_up;
+	}
+
+	if (slunkcrypt_random_bytes(buffer, LENGTH) != LENGTH)
+	{
+		FPUTS(T("\n\nWhoops: Failed to generate random message!\n\n"), stderr);
+		goto clean_up;
+	}
+
+	const uint64_t checksum_original = blake2s_compute(buffer, LENGTH);
+
+	ctx = slunkcrypt_alloc(nonce, (const uint8_t*)TEST_PASSPHRASE, strlen(TEST_PASSPHRASE), SLUNKCRYPT_ENCRYPT);
+	if (!ctx)
+	{
+		FPUTS(g_slunkcrypt_abort_flag ? T("\n\nProcess interrupted!\n\n") : T("\n\nWhoops: Failed to initialize encoder!\n\n"), stderr);
+		goto clean_up;
+	}
+
+	for (offset = 0U; offset < LENGTH; offset += chunk_size)
+	{
+		chunk_size = ((LENGTH - offset) > CHUNKZ_ENC) ? CHUNKZ_ENC : (LENGTH - offset);
+		status = slunkcrypt_inplace(ctx, buffer + offset, chunk_size);
+		if (status != SLUNKCRYPT_SUCCESS)
+		{
+			FPUTS((status == SLUNKCRYPT_ABORTED) ? T("\n\nProcess interrupted!\n\n") : T("\n\nWhoops: Failed to encrypt the message!\n\n"), stderr);
+			goto clean_up;
+		}
+	}
+
+	status = slunkcrypt_reset(ctx, nonce, (const uint8_t*)TEST_PASSPHRASE, strlen(TEST_PASSPHRASE), SLUNKCRYPT_DECRYPT);
+	if (status != SLUNKCRYPT_SUCCESS)
+	{
+		FPUTS((status == SLUNKCRYPT_ABORTED) ? T("\n\nProcess interrupted!\n\n") : T("\n\nWhoops: Failed to initialize decoder!\n\n"), stderr);
+		goto clean_up;
+	}
+
+	for (offset = 0U; offset < LENGTH; offset += chunk_size)
+	{
+		chunk_size = ((LENGTH - offset) > CHUNKZ_DEC) ? CHUNKZ_DEC : (LENGTH - offset);
+		status = slunkcrypt_inplace(ctx, buffer + offset, chunk_size);
+		if (status != SLUNKCRYPT_SUCCESS)
+		{
+			FPUTS((status == SLUNKCRYPT_ABORTED) ? T("\n\nProcess interrupted!\n\n") : T("\n\nWhoops: Failed to decrypt the message!\n\n"), stderr);
+			goto clean_up;
+		}
+	}
+
+	const uint64_t checksum_decrypted = blake2s_compute(buffer, LENGTH);
+	if (checksum_decrypted != checksum_original)
+	{
+		FPRINTF(stderr, T("\n\nWhoops: Checksum mismatch detected! [expected: 0x%016") T(PRIX64) T(", actual: 0x%016") T(PRIX64) T("]\n\n"), checksum_original, checksum_decrypted);
+		goto clean_up;
+	}
+
+	result = EXIT_SUCCESS;
+
+clean_up:
+
+	SLUNKCRYPT_SAFE_FREE(ctx);
+
+	if (buffer)
+	{
+		slunkcrypt_bzero(buffer, LENGTH);
+		free(buffer);
+	}
+
+	return result;
+}
+
 int run_selftest_routine(void)
 {
+	static const size_t ITERATIONS = 2U;
 	static const uint64_t TEST_NONCE[] = { 0x243F6A8885A308D3, 0x13198A2E03707344 };
+
 	const struct
 	{
 		const char* text;
@@ -136,15 +217,17 @@ int run_selftest_routine(void)
 		{ TEST_DATA_3, TEST_CHCK_ORIG_3, { TEST_CHCK_ENCR_3[0U], TEST_CHCK_ENCR_3[1U] } },
 	};
 
-	const size_t total = ARRAY_SIZE(TEST_NONCE) * ARRAY_SIZE(TEST_STAGE);
-	FPRINTF(stderr, T("Self-test is in progress, please be patient... stage %u/%u "), 0U, (unsigned)total);
+	const size_t total = ARRAY_SIZE(TEST_NONCE) * (ITERATIONS + ARRAY_SIZE(TEST_STAGE));
+	size_t count = 0U;
+
+	FPRINTF(stderr, T("Self-test is in progress, please be patient... stage %2u/%2u "), 0U, (unsigned)total);
 	fflush(stderr);
 
-	for (size_t i = 0U, count = 0U; i < ARRAY_SIZE(TEST_STAGE); ++i)
+	for (size_t i = 0U; i < ARRAY_SIZE(TEST_STAGE); ++i)
 	{
 		for (size_t j = 0U; j < ARRAY_SIZE(TEST_NONCE); ++j)
 		{
-			FPRINTF(stderr, T("\b\b\b\b%u/%u "), (unsigned)++count, (unsigned)total);
+			FPRINTF(stderr, T("\b\b\b\b\b\b%2u/%2u "), (unsigned)++count, (unsigned)total);
 			fflush(stderr);
 			if (run_testcase(TEST_STAGE[i].text, TEST_NONCE[j], TEST_STAGE[i].check_orig, TEST_STAGE[i].check_encr[j]) != EXIT_SUCCESS)
 			{
@@ -153,7 +236,20 @@ int run_selftest_routine(void)
 		}
 	}
 
-	FPRINTF(stderr, T("\b\b\b\b%u/%u\n\nCompleted successfully.\n\n"), (unsigned)total, (unsigned)total);
+	for (size_t i = 0U; i < ITERATIONS; ++i)
+	{
+		for (size_t j = 0U; j < ARRAY_SIZE(TEST_NONCE); ++j)
+		{
+			FPRINTF(stderr, T("\b\b\b\b\b\b%2u/%2u "), (unsigned)++count, (unsigned)total);
+			fflush(stderr);
+			if (run_stresstest(TEST_NONCE[j]) != EXIT_SUCCESS)
+			{
+				return EXIT_FAILURE;
+			}
+		}
+	}
+
+	FPRINTF(stderr, T("\b\b\b\b\b\b%2u/%2u\n\nCompleted successfully.\n\n"), (unsigned)total, (unsigned)total);
 	fflush(stderr);
 
 	return EXIT_SUCCESS;
diff --git a/libslunkcrypt/include/slunkcrypt.h b/libslunkcrypt/include/slunkcrypt.h
index ce9c7f8..fc57c87 100644
--- a/libslunkcrypt/include/slunkcrypt.h
+++ b/libslunkcrypt/include/slunkcrypt.h
@@ -128,6 +128,11 @@ SLUNKCRYPT_API int slunkcrypt_inplace(const slunkcrypt_t context, uint8_t *const
 SLUNKCRYPT_API size_t slunkcrypt_random_bytes(uint8_t *const buffer, const size_t length);
 SLUNKCRYPT_API void slunkcrypt_bzero(void *const buffer, const size_t length);
 
+/*
+ * Helper macros
+ */
+#define SLUNKCRYPT_SAFE_FREE(X) do { if((X) != SLUNKCRYPT_NULL) { slunkcrypt_free((X)); X = SLUNKCRYPT_NULL; } } while(0)
+
 #ifdef __cplusplus
 }
 #endif