diff --git a/src/internal.c b/src/internal.c
index 324ec932cd..0509918f50 100644
--- a/src/internal.c
+++ b/src/internal.c
@@ -23310,13 +23310,17 @@ int SendFinished(WOLFSSL* ssl)
  * Returns 0 on success
  */
 static int CreateOcspRequest(WOLFSSL* ssl, OcspRequest* request,
-                             DecodedCert* cert, byte* certData, word32 length)
+                             DecodedCert* cert, byte* certData, word32 length,
+                             byte *ctxOwnsRequest)
 {
     int ret;
 
     if (request != NULL)
         XMEMSET(request, 0, sizeof(OcspRequest));
 
+    if (ctxOwnsRequest!= NULL)
+        *ctxOwnsRequest = 0;
+
     InitDecodedCert(cert, certData, length, ssl->heap);
     /* TODO: Setup async support here */
     ret = ParseCertRelative(cert, CERT_TYPE, VERIFY, SSL_CM(ssl), NULL);
@@ -23330,8 +23334,11 @@ static int CreateOcspRequest(WOLFSSL* ssl, OcspRequest* request,
         if (!ssl->buffers.weOwnCert) {
             wolfSSL_Mutex* ocspLock = &SSL_CM(ssl)->ocsp_stapling->ocspLock;
             if (wc_LockMutex(ocspLock) == 0) {
-                if (ssl->ctx->certOcspRequest == NULL)
+                if (ssl->ctx->certOcspRequest == NULL) {
                     ssl->ctx->certOcspRequest = request;
+                    if (ctxOwnsRequest!= NULL)
+                        *ctxOwnsRequest = 1;
+                }
                 wc_UnLockMutex(ocspLock);
             }
         }
@@ -23360,6 +23367,7 @@ int CreateOcspResponse(WOLFSSL* ssl, OcspRequest** ocspRequest,
     int          ret = 0;
     OcspRequest* request = NULL;
     byte createdRequest  = 0;
+    byte ctxOwnsRequest = 0;
 
     if (ssl == NULL || ocspRequest == NULL || response == NULL)
         return BAD_FUNC_ARG;
@@ -23397,7 +23405,7 @@ int CreateOcspResponse(WOLFSSL* ssl, OcspRequest** ocspRequest,
         createdRequest = 1;
         if (ret == 0) {
             ret = CreateOcspRequest(ssl, request, cert, der->buffer,
-                                                                   der->length);
+                      der->length, &ctxOwnsRequest);
         }
 
         if (ret != 0) {
@@ -23424,7 +23432,7 @@ int CreateOcspResponse(WOLFSSL* ssl, OcspRequest** ocspRequest,
     }
 
     /* free request up if error case found otherwise return it */
-    if (ret != 0 && createdRequest) {
+    if (ret != 0 && createdRequest && !ctxOwnsRequest) {
         FreeOcspRequest(request);
         XFREE(request, ssl->heap, DYNAMIC_TYPE_OCSP_REQUEST);
     }
@@ -24119,6 +24127,7 @@ int SendCertificateStatus(WOLFSSL* ssl)
         {
             OcspRequest* request = ssl->ctx->certOcspRequest;
             buffer responses[1 + MAX_CHAIN_DEPTH];
+            byte ctxOwnsRequest = 0;
             int i = 0;
 
             XMEMSET(responses, 0, sizeof(responses));
@@ -24177,7 +24186,7 @@ int SendCertificateStatus(WOLFSSL* ssl)
                             break;
 
                         ret = CreateOcspRequest(ssl, request, cert, der.buffer,
-                                                der.length);
+                                                der.length, &ctxOwnsRequest);
                         if (ret == 0) {
                             request->ssl = ssl;
                         ret = CheckOcspRequest(SSL_CM(ssl)->ocsp_stapling,
@@ -24192,12 +24201,13 @@ int SendCertificateStatus(WOLFSSL* ssl)
 
 
                             i++;
-                            FreeOcspRequest(request);
+                            if (!ctxOwnsRequest)
+                                FreeOcspRequest(request);
                         }
                     }
                 }
-
-                XFREE(request, ssl->heap, DYNAMIC_TYPE_OCSP_REQUEST);
+                if (!ctxOwnsRequest)
+                    XFREE(request, ssl->heap, DYNAMIC_TYPE_OCSP_REQUEST);
             #ifdef WOLFSSL_SMALL_STACK
                 XFREE(cert, ssl->heap, DYNAMIC_TYPE_DCERT);
             #endif
diff --git a/tests/api.c b/tests/api.c
index 8a140e1819..61083e4b29 100644
--- a/tests/api.c
+++ b/tests/api.c
@@ -82888,6 +82888,60 @@ static int test_wolfSSL_SendUserCanceled(void)
 #endif
     return EXPECT_RESULT();
 }
+#if defined(HAVE_MANUAL_MEMIO_TESTS_DEPENDENCIES) && \
+    defined(HAVE_OCSP) && \
+    defined(HAVE_CERTIFICATE_STATUS_REQUEST) && \
+    !defined(WOLFSSL_NO_TLS12)
+static int test_ocsp_callback_fails_cb(void* ctx, const char* url, int urlSz,
+                        byte* ocspReqBuf, int ocspReqSz, byte** ocspRespBuf)
+{
+    (void)ctx;
+    (void)url;
+    (void)urlSz;
+    (void)ocspReqBuf;
+    (void)ocspReqSz;
+    (void)ocspRespBuf;
+    return -1;
+}
+static int test_ocsp_callback_fails(void)
+{
+    WOLFSSL_CTX *ctx_c = NULL;
+    WOLFSSL_CTX *ctx_s = NULL;
+    WOLFSSL *ssl_c = NULL;
+    WOLFSSL *ssl_s = NULL;
+    struct test_memio_ctx test_ctx;
+    EXPECT_DECLS;
+
+    XMEMSET(&test_ctx, 0, sizeof(test_ctx));
+    ExpectIntEQ(test_memio_setup(&test_ctx, &ctx_c, &ctx_s, &ssl_c, &ssl_s,
+            wolfTLSv1_2_client_method, wolfTLSv1_2_server_method), 0);
+    ExpectIntEQ(wolfSSL_CTX_EnableOCSPStapling(ctx_c), WOLFSSL_SUCCESS);
+    ExpectIntEQ(wolfSSL_CTX_EnableOCSPStapling(ctx_s), WOLFSSL_SUCCESS);
+    ExpectIntEQ(wolfSSL_UseOCSPStapling(ssl_c, WOLFSSL_CSR_OCSP,0), WOLFSSL_SUCCESS);
+    /* override URL to avoid exing from SendCertificateStatus because of no AuthInfo on the certificate */
+    ExpectIntEQ(wolfSSL_CTX_SetOCSP_OverrideURL(ctx_s, "http://dummy.test"), WOLFSSL_SUCCESS);
+    ExpectIntEQ(wolfSSL_CTX_EnableOCSP(ctx_s, WOLFSSL_OCSP_NO_NONCE    | WOLFSSL_OCSP_URL_OVERRIDE), WOLFSSL_SUCCESS);
+    ExpectIntEQ(wolfSSL_CTX_load_verify_locations(ctx_s, caCertFile, 0), WOLFSSL_SUCCESS);
+    ExpectIntEQ(wolfSSL_SetOCSP_Cb(ssl_s, test_ocsp_callback_fails_cb, NULL, NULL), WOLFSSL_SUCCESS);
+    ExpectIntEQ(test_memio_do_handshake(ssl_c, ssl_s, 10, NULL), -1);
+    ExpectIntEQ(wolfSSL_get_error(ssl_s, -1), OCSP_INVALID_STATUS);
+
+    wolfSSL_free(ssl_c);
+    wolfSSL_free(ssl_s);
+    wolfSSL_CTX_free(ctx_c);
+    wolfSSL_CTX_free(ctx_s);
+
+    return EXPECT_RESULT();
+}
+#else
+static int test_ocsp_callback_fails(void)
+{
+    return TEST_SKIPPED;
+}
+#endif /* defined(HAVE_MANUAL_MEMIO_TESTS_DEPENDENCIES) && \
+    defined(HAVE_OCSP) && \
+    defined(HAVE_CERTIFICATE_STATUS_REQUEST) */
+
 
 /*----------------------------------------------------------------------------*
  | Main
@@ -84120,6 +84174,7 @@ TEST_CASE testCases[] = {
     TEST_DECL(test_wolfSSL_UseOCSPStapling),
     TEST_DECL(test_wolfSSL_UseOCSPStaplingV2),
     TEST_DECL(test_self_signed_stapling),
+    TEST_DECL(test_ocsp_callback_fails),
 
     /* Multicast */
     TEST_DECL(test_wolfSSL_mcast),