diff --git a/src/internal.c b/src/internal.c
index cd25cfc400..34fca4f8d6 100644
--- a/src/internal.c
+++ b/src/internal.c
@@ -19,8 +19,6 @@
  * Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA 02110-1335, USA
  */
 
-
-
 #ifdef HAVE_CONFIG_H
     #include <config.h>
 #endif
@@ -25063,6 +25061,20 @@ static int SendAlert_ex(WOLFSSL* ssl, int severity, int type)
         }
     #endif
 
+    /*
+     * We check if we are trying to send a
+     * CLOSE_NOTIFY alert.
+     * */
+    if (type == close_notify) {
+        if (!ssl->options.sentNotify) {
+            ssl->options.sentNotify = 1;
+        }
+        else {
+            /* CLOSE_NOTIFY already sent */
+            return 0;
+        }
+    }
+
     ssl->buffers.outputBuffer.length += sendSz;
 
     ret = SendBuffered(ssl);
diff --git a/tests/api.c b/tests/api.c
index 68b1d4c361..b920738521 100644
--- a/tests/api.c
+++ b/tests/api.c
@@ -81186,6 +81186,90 @@ static int test_extra_alerts_bad_psk(void)
 }
 #endif
 
+#if defined(OPENSSL_EXTRA) && defined(HAVE_MANUAL_MEMIO_TESTS_DEPENDENCIES) && !defined(WOLFSSL_NO_TLS12)
+/*
+ * Emulates wolfSSL_shutdown that goes on EAGAIN,
+ * by returning on output WOLFSSL_ERROR_WANT_WRITE.*/
+static int custom_wolfSSL_shutdown(WOLFSSL *ssl, char *buf,
+        int sz, void *ctx)
+{
+    (void)ssl;
+    (void)buf;
+    (void)ctx;
+    (void)sz;
+
+    return WOLFSSL_CBIO_ERR_WANT_WRITE;
+}
+
+static int test_multiple_alerts_EAGAIN(void)
+{
+    EXPECT_DECLS;
+    size_t size_of_last_packet = 0;
+
+    /* declare wolfSSL objects */
+    struct test_memio_ctx test_ctx;
+    WOLFSSL_CTX *ctx_c = NULL, *ctx_s = NULL;
+    WOLFSSL *ssl_c = NULL, *ssl_s = NULL;
+
+    XMEMSET(&test_ctx, 0, sizeof(test_ctx));
+
+    /* Create and initialize WOLFSSL_CTX and WOLFSSL objects */
+#ifdef USE_TLSV13
+    ExpectIntEQ(test_memio_setup(&test_ctx, &ctx_c, &ctx_s, &ssl_c, &ssl_s,
+          wolfTLSv1_3_client_method,  wolfTLSv1_3_server_method), 0);
+#else
+    ExpectIntEQ(test_memio_setup(&test_ctx, &ctx_c, &ctx_s, &ssl_c, &ssl_s,
+         wolfTLSv1_2_client_method, wolfTLSv1_2_server_method), 0);
+#endif
+    ExpectNotNull(ctx_c);
+    ExpectNotNull(ssl_c);
+    ExpectNotNull(ctx_s);
+    ExpectNotNull(ssl_s);
+
+    /* Load client certificates into WOLFSSL_CTX */
+    ExpectIntEQ(wolfSSL_CTX_load_verify_locations(ctx_c, "./certs/ca-cert.pem", NULL), WOLFSSL_SUCCESS);
+
+    ExpectIntEQ(test_memio_do_handshake(ssl_c, ssl_s, 10, NULL), 0);
+
+    /*
+     * We set the custom callback for the IO to emulate multiple EAGAINs
+     * on shutdown, so we can check that we don't send multiple packets.
+     * */
+    wolfSSL_SSLSetIOSend(ssl_c, custom_wolfSSL_shutdown);
+
+    /*
+     * We call wolfSSL_shutdown multiple times to reproduce the behaviour,
+     * to check that it doesn't add the CLOSE_NOTIFY packet multiple times
+     * on the output buffer.
+     * */
+    wolfSSL_shutdown(ssl_c);
+    wolfSSL_shutdown(ssl_c);
+
+    if (ssl_c != NULL) {
+        size_of_last_packet = ssl_c->buffers.outputBuffer.length;
+    }
+    wolfSSL_shutdown(ssl_c);
+
+    /*
+     * Finally we check the length of the output buffer.
+     * */
+    ExpectIntEQ((ssl_c->buffers.outputBuffer.length - size_of_last_packet), 0);
+
+    /* Cleanup and return */
+    wolfSSL_CTX_free(ctx_c);
+    wolfSSL_free(ssl_c);
+    wolfSSL_CTX_free(ctx_s);
+    wolfSSL_free(ssl_s);
+
+    return EXPECT_RESULT();
+}
+#else
+static int test_multiple_alerts_EAGAIN(void)
+{
+    return TEST_SKIPPED;
+}
+#endif
+
 #if defined(WOLFSSL_TLS13) && defined(HAVE_MANUAL_MEMIO_TESTS_DEPENDENCIES)\
     && !defined(NO_PSK)
 static unsigned int test_tls13_bad_psk_binder_client_cb(WOLFSSL* ssl,
@@ -86697,6 +86781,7 @@ TEST_CASE testCases[] = {
     TEST_DECL(test_extra_alerts_wrong_cs),
     TEST_DECL(test_extra_alerts_skip_hs),
     TEST_DECL(test_extra_alerts_bad_psk),
+    TEST_DECL(test_multiple_alerts_EAGAIN),
     TEST_DECL(test_tls13_bad_psk_binder),
     /* Can't memory test as client/server Asserts. */
     TEST_DECL(test_harden_no_secure_renegotiation),