--- a/cmake/ssl.cmake
+++ b/cmake/ssl.cmake
@@ -186,7 +186,8 @@ 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)
        SET(HAVE_TLSv13 1)
        IF(SOLARIS)
@@ -196,7 +197,7 @@ MACRO (MYSQL_CHECK_SSL)
     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)
     ELSE()
--- a/sql/auth/sha2_password_common.cc
+++ b/sql/auth/sha2_password_common.cc
@@ -116,7 +116,8 @@ bool SHA256_digest::retrieve_digest(unsigned char *digest,
     DBUG_RETURN(true);
   }
   m_ok= EVP_DigestFinal_ex(md_context, m_digest, NULL);
-#if defined(HAVE_WOLFSSL) || OPENSSL_VERSION_NUMBER < 0x10100000L
+#if defined(HAVE_WOLFSSL) || OPENSSL_VERSION_NUMBER < 0x10100000L || \
+    (defined(LIBRESSL_VERSION_NUMBER) && LIBRESSL_VERSION_NUMBER < 0x02090000fL)
   EVP_MD_CTX_cleanup(md_context);
 #else  /* OPENSSL_VERSION_NUMBER < 0x10100000L */
   EVP_MD_CTX_reset(md_context);
--- a/sql/mysqld.cc
+++ b/sql/mysqld.cc
@@ -3419,7 +3419,7 @@ int warn_self_signed_ca()
 static int init_ssl()
 {
 #ifdef HAVE_OPENSSL
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
   CRYPTO_malloc_init();
 #else /* OPENSSL_VERSION_NUMBER < 0x10100000L */
   OPENSSL_malloc_init();
--- a/vio/viosslfactories.c
+++ b/vio/viosslfactories.c
@@ -123,21 +123,19 @@ static DH *get_dh2048(void)
   DH *dh;
   if ((dh=DH_new()))
   {
-    BIGNUM *p= BN_bin2bn(dh2048_p, sizeof(dh2048_p), NULL);
-    BIGNUM *g= BN_bin2bn(dh2048_g, sizeof(dh2048_g), NULL);
-    if (!p || !g
-#if OPENSSL_VERSION_NUMBER >= 0x10100000L
-        || !DH_set0_pqg(dh, p, NULL, g)
-#endif /* OPENSSL_VERSION_NUMBER >= 0x10100000L */
-    ) {
-      /* DH_free() will free 'p' and 'g' at once. */
+    BIGNUM *p = BN_bin2bn(dh2048_p,sizeof(dh2048_p), NULL);
+    BIGNUM *g = BN_bin2bn(dh2048_g,sizeof(dh2048_g), NULL);
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
+    dh->p=p;
+    dh->g=g;
+    if (! dh->p || ! dh->g)
+#else
+    if (!DH_set0_pqg(dh, p, NULL, g))
+#endif
+    {
       DH_free(dh);
-      return NULL;
+      dh = NULL;
     }
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
-    dh->p= p;
-    dh->g= g;
-#endif /* OPENSSL_VERSION_NUMBER < 0x10100000L */
   }
   return(dh);
 }