diff -ru a/openssl-compat.h b/openssl-compat.h
--- a/openssl-compat.h
+++ b/openssl-compat.h
@@ -1,7 +1,7 @@
 #ifndef OPENSSL_COMPAT_H
 #define OPENSSL_COMPAT_H
 
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 
 static inline BIO_METHOD *BIO_meth_new(int type, const char *name)
 {
@@ -30,6 +30,6 @@
 
 #define TLS_method SSLv23_method
 
-#endif /* OPENSSL_VERSION_NUMBER < 0x10100000L */
+#endif /* OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER) */
 
 #endif /* OPENSSL_COMPAT_H */
diff -ru a/sample/https-client.c b/sample/https-client.c
--- a/sample/https-client.c
+++ b/sample/https-client.c
@@ -312,7 +312,7 @@
 	}
 	uri[sizeof(uri) - 1] = '\0';
 
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 	// Initialize OpenSSL
 	SSL_library_init();
 	ERR_load_crypto_strings();
@@ -480,7 +480,7 @@
 		SSL_CTX_free(ssl_ctx);
 	if (type == HTTP && ssl)
 		SSL_free(ssl);
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 	EVP_cleanup();
 	ERR_free_strings();
 
@@ -492,7 +492,7 @@
 	CRYPTO_cleanup_all_ex_data();
 
 	sk_SSL_COMP_free(SSL_COMP_get_compression_methods());
-#endif /*OPENSSL_VERSION_NUMBER < 0x10100000L */
+#endif /*OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER) */
 
 #ifdef _WIN32
 	WSACleanup();
diff -ru a/sample/le-proxy.c b/sample/le-proxy.c
--- a/sample/le-proxy.c
+++ b/sample/le-proxy.c
@@ -259,7 +259,7 @@
 
 	if (use_ssl) {
 		int r;
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 		SSL_library_init();
 		ERR_load_crypto_strings();
 		SSL_load_error_strings();
diff -ru a/sample/openssl_hostname_validation.c b/sample/openssl_hostname_validation.c
--- a/sample/openssl_hostname_validation.c
+++ b/sample/openssl_hostname_validation.c
@@ -48,7 +48,7 @@
 
 #define HOSTNAME_MAX_SIZE 255
 
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 #define ASN1_STRING_get0_data ASN1_STRING_data
 #endif
 
diff -ru a/test/regress_ssl.c b/test/regress_ssl.c
--- a/test/regress_ssl.c
+++ b/test/regress_ssl.c
@@ -186,7 +186,7 @@
 void
 init_ssl(void)
 {
-#if OPENSSL_VERSION_NUMBER < 0x10100000L
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 	SSL_library_init();
 	ERR_load_crypto_strings();
 	SSL_load_error_strings();
@@ -194,6 +194,10 @@
 	if (SSLeay() != OPENSSL_VERSION_NUMBER) {
 		TT_DECLARE("WARN", ("Version mismatch for openssl: compiled with %lx but running with %lx", (unsigned long)OPENSSL_VERSION_NUMBER, (unsigned long) SSLeay()));
 	}
+	if (SSLeay() != LIBRESSL_VERSION_NUMBER) {
+		TT_DECLARE("WARN", ("Version mismatch for libressl: compiled with %lx but running with %lx", (unsigned long)LIBRESSL_VERSION_NUMBER, (unsigned long) SSLeay()));
+	}
+
 #endif
 }