--- a/cmake/ssl.cmake
+++ b/cmake/ssl.cmake
@@ -229,13 +229,14 @@ MACRO (MYSQL_CHECK_SSL)
         OPENSSL_FIX_VERSION "${OPENSSL_VERSION_NUMBER}"
         )
     ENDIF()
-    IF("${OPENSSL_MAJOR_VERSION}.${OPENSSL_MINOR_VERSION}.${OPENSSL_FIX_VERSION}" VERSION_GREATER "1.1.0")
+    CHECK_SYMBOL_EXISTS(TLS1_3_VERSION "openssl/tls1.h" HAVE_TLS1_3_VERSION)
+    IF(HAVE_TLS1_3_VERSION)
        ADD_DEFINITIONS(-DHAVE_TLSv13)
     ENDIF()
     IF(OPENSSL_INCLUDE_DIR AND
        OPENSSL_LIBRARY   AND
        CRYPTO_LIBRARY      AND
-       OPENSSL_MAJOR_VERSION STREQUAL "1"
+       OPENSSL_MAJOR_VERSION VERSION_GREATER_EQUAL "1"
       )
       SET(OPENSSL_FOUND TRUE)
       FIND_PROGRAM(OPENSSL_EXECUTABLE openssl
--- a/mysys/my_md5.cc
+++ b/mysys/my_md5.cc
@@ -56,7 +56,9 @@ static void my_md5_hash(unsigned char *digest, unsigned const char *buf,
 int compute_md5_hash(char *digest, const char *buf, int len) {
   int retval = 0;
   int fips_mode = 0;
+#ifndef LIBRESSL_VERSION_NUMBER
   fips_mode = FIPS_mode();
+#endif
   /* If fips mode is ON/STRICT restricted method calls will result into abort,
    * skipping call. */
   if (fips_mode == 0) {
--- a/plugin/group_replication/libmysqlgcs/src/bindings/xcom/xcom/xcom_ssl_transport.c
+++ b/plugin/group_replication/libmysqlgcs/src/bindings/xcom/xcom/xcom_ssl_transport.c
@@ -329,6 +329,7 @@ error:
   return 1;
 }
 
+#ifndef LIBRESSL_VERSION_NUMBER
 #define OPENSSL_ERROR_LENGTH 512
 static int configure_ssl_fips_mode(const uint fips_mode) {
   int rc = -1;
@@ -352,6 +353,7 @@ static int configure_ssl_fips_mode(const uint fips_mode) {
 EXIT:
   return rc;
 }
+#endif
 
 static int configure_ssl_ca(SSL_CTX *ssl_ctx, const char *ca_file,
                             const char *ca_path) {
@@ -555,10 +557,12 @@ int xcom_init_ssl(const char *server_key_file, const char *server_cert_file,
   int verify_server = SSL_VERIFY_NONE;
   int verify_client = SSL_VERIFY_NONE;
 
+#ifndef LIBRESSL_VERSION_NUMBER
   if (configure_ssl_fips_mode(ssl_fips_mode) != 1) {
     G_ERROR("Error setting the ssl fips mode");
     goto error;
   }
+#endif
 
   SSL_library_init();
   SSL_load_error_strings();
@@ -622,7 +626,7 @@ error:
 void xcom_cleanup_ssl() {
   if (!xcom_use_ssl()) return;
 
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
   ERR_remove_thread_state(0);
 #endif /* OPENSSL_VERSION_NUMBER < 0x10100000L */
 }
--- a/plugin/x/client/xconnection_impl.cc
+++ b/plugin/x/client/xconnection_impl.cc
@@ -520,6 +520,7 @@ XError Connection_impl::get_ssl_error(const int error_id) {
   return XError(CR_SSL_CONNECTION_ERROR, buffer);
 }
 
+#ifndef LIBRESSL_VERSION_NUMBER
 /**
   Set fips mode in openssl library,
   When we set fips mode ON/STRICT, it will perform following operations:
@@ -559,6 +560,7 @@ int set_fips_mode(const uint32_t fips_mode,
 EXIT:
   return rc;
 }
+#endif
 
 XError Connection_impl::activate_tls() {
   if (nullptr == m_vio) return get_socket_error(SOCKET_ECONNRESET);
@@ -569,12 +571,14 @@ XError Connection_impl::activate_tls() {
   if (!m_context->m_ssl_config.is_configured())
     return XError{CR_SSL_CONNECTION_ERROR, ER_TEXT_TLS_NOT_CONFIGURATED, true};
 
+#ifndef LIBRESSL_VERSION_NUMBER
   char err_string[OPENSSL_ERROR_LENGTH] = {'\0'};
   if (set_fips_mode(
           static_cast<uint32_t>(m_context->m_ssl_config.m_ssl_fips_mode),
           err_string) != 1) {
     return XError{CR_SSL_CONNECTION_ERROR, err_string, true};
   }
+#endif
   auto ssl_ctx_flags = process_tls_version(
       details::null_when_empty(m_context->m_ssl_config.m_tls_version));
 
--- a/router/src/http/src/tls_client_context.cc
+++ b/router/src/http/src/tls_client_context.cc
@@ -54,7 +54,7 @@ void TlsClientContext::verify(TlsVerify verify) {
 
 void TlsClientContext::cipher_suites(const std::string &ciphers) {
 // TLSv1.3 ciphers are controlled via SSL_CTX_set_ciphersuites()
-#if OPENSSL_VERSION_NUMBER >= ROUTER_OPENSSL_VERSION(1, 1, 1)
+#ifdef TLS1_3_VERSION
   if (1 != SSL_CTX_set_ciphersuites(ssl_ctx_.get(), ciphers.c_str())) {
     throw TlsError("set-cipher-suites");
   }
--- a/router/src/http/src/tls_context.cc
+++ b/router/src/http/src/tls_context.cc
@@ -91,7 +91,7 @@ static int o11x_version(TlsVersion version) {
       return TLS1_1_VERSION;
     case TlsVersion::TLS_1_2:
       return TLS1_2_VERSION;
-#if OPENSSL_VERSION_NUMBER >= ROUTER_OPENSSL_VERSION(1, 1, 1)
+#ifdef TLS1_3_VERSION
     case TlsVersion::TLS_1_3:
       return TLS1_3_VERSION;
 #endif
@@ -120,9 +120,11 @@ void TlsContext::version_range(TlsVersion min_version, TlsVersion max_version) {
   switch (min_version) {
     default:
       // unknown, leave all disabled
+#ifdef TLS1_3_VERSION
       // fallthrough
     case TlsVersion::TLS_1_3:
       opts |= SSL_OP_NO_TLSv1_2;
+#endif
       // fallthrough
     case TlsVersion::TLS_1_2:
       opts |= SSL_OP_NO_TLSv1_1;
@@ -170,8 +172,10 @@ TlsVersion TlsContext::min_version() const {
       return TlsVersion::TLS_1_1;
     case TLS1_2_VERSION:
       return TlsVersion::TLS_1_2;
+#ifdef TLS1_3_VERSION
     case TLS1_3_VERSION:
       return TlsVersion::TLS_1_3;
+#endif
     case 0:
       return TlsVersion::AUTO;
     default:
@@ -230,7 +234,8 @@ TlsContext::InfoCallback TlsContext::info_callback() const {
 }
 
 int TlsContext::security_level() const {
-#if OPENSSL_VERSION_NUMBER >= ROUTER_OPENSSL_VERSION(1, 1, 0)
+#if OPENSSL_VERSION_NUMBER >= ROUTER_OPENSSL_VERSION(1, 1, 0) && \
+    !defined(LIBRESSL_VERSION_NUMBER)
   return SSL_CTX_get_security_level(ssl_ctx_.get());
 #else
   return 0;
--- a/router/src/http/src/tls_server_context.cc
+++ b/router/src/http/src/tls_server_context.cc
@@ -166,7 +166,8 @@ void TlsServerContext::init_tmp_dh(const std::string &dh_params) {
     }
 
   } else {
-#if OPENSSL_VERSION_NUMBER >= ROUTER_OPENSSL_VERSION(1, 1, 0)
+#if OPENSSL_VERSION_NUMBER >= ROUTER_OPENSSL_VERSION(1, 1, 0) && \
+    !defined(LIBRESSL_VERSION_NUMBER)
     dh2048.reset(DH_get_2048_256());
 #else
     /*
--- a/sql-common/client.cc
+++ b/sql-common/client.cc
@@ -7730,7 +7730,7 @@ int STDCALL mysql_options(MYSQL *mysql, enum mysql_option option,
 #endif
       break;
     case MYSQL_OPT_SSL_FIPS_MODE: {
-#if defined(HAVE_OPENSSL)
+#if defined(HAVE_OPENSSL) && !defined(LIBRESSL_VERSION_NUMBER)
       char ssl_err_string[OPENSSL_ERROR_LENGTH] = {'\0'};
       ENSURE_EXTENSIONS_PRESENT(&mysql->options);
       mysql->options.extension->ssl_fips_mode = *static_cast<const uint *>(arg);
--- a/sql/mysqld.cc
+++ b/sql/mysqld.cc
@@ -4818,7 +4818,7 @@ static int init_thread_environment() {
 
 static PSI_memory_key key_memory_openssl = PSI_NOT_INSTRUMENTED;
 
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 #define FILE_LINE_ARGS
 #else
 #define FILE_LINE_ARGS , const char *, int
@@ -4854,12 +4854,14 @@ static void init_ssl() {
 }
 
 static int init_ssl_communication() {
+#ifndef LIBRESSL_VERSION_NUMBER
   char ssl_err_string[OPENSSL_ERROR_LENGTH] = {'\0'};
   int ret_fips_mode = set_fips_mode(opt_ssl_fips_mode, ssl_err_string);
   if (ret_fips_mode != 1) {
     LogErr(ERROR_LEVEL, ER_SSL_FIPS_MODE_ERROR, ssl_err_string);
     return 1;
   }
+#endif
   if (SslAcceptorContext::singleton_init(opt_use_ssl)) return 1;
 
 #if OPENSSL_VERSION_NUMBER < 0x10100000L
--- a/sql/sys_vars.cc
+++ b/sql/sys_vars.cc
@@ -4417,6 +4417,7 @@ static Sys_var_ulong Sys_max_execution_time(
     HINT_UPDATEABLE SESSION_VAR(max_execution_time), CMD_LINE(REQUIRED_ARG),
     VALID_RANGE(0, ULONG_MAX), DEFAULT(0), BLOCK_SIZE(1));
 
+#ifndef LIBRESSL_VERSION_NUMBER
 static bool update_fips_mode(sys_var *, THD *, enum_var_type) {
   char ssl_err_string[OPENSSL_ERROR_LENGTH] = {'\0'};
   if (set_fips_mode(opt_ssl_fips_mode, ssl_err_string) != 1) {
@@ -4427,15 +4428,30 @@ static bool update_fips_mode(sys_var *, THD *, enum_var_type) {
     return false;
   }
 }
+#endif
 
+#if defined(LIBRESSL_VERSION_NUMBER)
+static const char *ssl_fips_mode_names[] = {"OFF", 0};
+#else
 static const char *ssl_fips_mode_names[] = {"OFF", "ON", "STRICT", 0};
+#endif
 static Sys_var_enum Sys_ssl_fips_mode(
     "ssl_fips_mode",
     "SSL FIPS mode (applies only for OpenSSL); "
+#ifndef LIBRESSL_VERSION_NUMBER
     "permitted values are: OFF, ON, STRICT",
+#else
+    "permitted values are: OFF",
+#endif
     GLOBAL_VAR(opt_ssl_fips_mode), CMD_LINE(REQUIRED_ARG, OPT_SSL_FIPS_MODE),
     ssl_fips_mode_names, DEFAULT(0), NO_MUTEX_GUARD, NOT_IN_BINLOG,
-    ON_CHECK(NULL), ON_UPDATE(update_fips_mode), NULL);
+    ON_CHECK(NULL),
+#ifndef LIBRESSL_VERSION_NUMBER
+    ON_UPDATE(update_fips_mode),
+#else
+    ON_UPDATE(NULL),
+#endif
+    NULL);
 
 #if defined(HAVE_OPENSSL)
 static Sys_var_bool Sys_auto_generate_certs(
--- a/vio/viossl.cc
+++ b/vio/viossl.cc
@@ -45,7 +45,7 @@
   BIO_set_callback_ex was added in openSSL 1.1.1
   For older openSSL, use the deprecated BIO_set_callback.
 */
-#if OPENSSL_VERSION_NUMBER >= 0x10101000L
+#if OPENSSL_VERSION_NUMBER >= 0x10101000L && !defined(LIBRESSL_VERSION_NUMBER)
 #define HAVE_BIO_SET_CALLBACK_EX
 #endif
 
@@ -637,7 +637,7 @@ static int ssl_do(struct st_VioSSLFd *ptr, Vio *vio, long timeout,
 #if !defined(DBUG_OFF)
     {
       STACK_OF(SSL_COMP) *ssl_comp_methods = NULL;
-      ssl_comp_methods = SSL_COMP_get_compression_methods();
+      ssl_comp_methods = (STACK_OF(SSL_COMP) *)SSL_COMP_get_compression_methods();
       n = sk_SSL_COMP_num(ssl_comp_methods);
       DBUG_PRINT("info", ("Available compression methods:\n"));
       if (n == 0)
@@ -645,7 +645,7 @@ static int ssl_do(struct st_VioSSLFd *ptr, Vio *vio, long timeout,
       else
         for (j = 0; j < n; j++) {
           SSL_COMP *c = sk_SSL_COMP_value(ssl_comp_methods, j);
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
           DBUG_PRINT("info", ("  %d: %s\n", c->id, c->name));
 #else  /* OPENSSL_VERSION_NUMBER < 0x10100000L */
           DBUG_PRINT("info",
--- a/vio/viosslfactories.cc
+++ b/vio/viosslfactories.cc
@@ -420,6 +420,7 @@ void ssl_start() {
   }
 }
 
+#ifndef LIBRESSL_VERSION_NUMBER
 /**
   Set fips mode in openssl library,
   When we set fips mode ON/STRICT, it will perform following operations:
@@ -473,6 +474,7 @@ EXIT:
   @returns openssl current fips mode
 */
 uint get_fips_mode() { return FIPS_mode(); }
+#endif
 
 long process_tls_version(const char *tls_version) {
   const char *separator = ",";