diff --git a/src/openvpn/openssl_compat.h b/src/openvpn/openssl_compat.h
index 05ec4e95..4931fad3 100644
--- a/src/openvpn/openssl_compat.h
+++ b/src/openvpn/openssl_compat.h
@@ -661,4 +661,67 @@ EC_GROUP_order_bits(const EC_GROUP *group)
 #define RSA_F_RSA_OSSL_PRIVATE_ENCRYPT       RSA_F_RSA_EAY_PRIVATE_ENCRYPT
 #endif
 
+#ifndef SSL_CTX_get_min_proto_version
+/** Dummy SSL_CTX_get_min_proto_version for OpenSSL < 1.1 (not really needed) */
+static inline int
+SSL_CTX_get_min_proto_version(SSL_CTX *ctx)
+{
+    return 0;
+}
+#endif /* SSL_CTX_get_min_proto_version */
+
+#ifndef SSL_CTX_set_min_proto_version
+/** Mimics SSL_CTX_set_min_proto_version for OpenSSL < 1.1 */
+static inline void
+SSL_CTX_set_min_proto_version(SSL_CTX *ctx, long tls_ver_min)
+{
+    long sslopt = SSL_OP_NO_SSLv2 | SSL_OP_NO_SSLv3; /* Never do < TLS 1.0 */
+
+    if (tls_ver_min > TLS1_VERSION)
+    {
+        sslopt |= SSL_OP_NO_TLSv1;
+    }
+#ifdef SSL_OP_NO_TLSv1_1
+    if (tls_ver_min > TLS1_1_VERSION)
+    {
+        sslopt |= SSL_OP_NO_TLSv1_1;
+    }
+#endif
+#ifdef SSL_OP_NO_TLSv1_2
+    if (tls_ver_min > TLS1_2_VERSION)
+    {
+        sslopt |= SSL_OP_NO_TLSv1_2;
+    }
+#endif
+    SSL_CTX_set_options(ctx, sslopt);
+}
+#endif /* SSL_CTX_set_min_proto_version */
+
+#ifndef SSL_CTX_set_max_proto_version
+/** Mimics SSL_CTX_set_max_proto_version for OpenSSL < 1.1 */
+static inline void
+SSL_CTX_set_max_proto_version(SSL_CTX *ctx, long tls_ver_max)
+{
+    long sslopt = 0;
+
+    if (tls_ver_max < TLS1_VERSION)
+    {
+        sslopt |= SSL_OP_NO_TLSv1;
+    }
+#ifdef SSL_OP_NO_TLSv1_1
+    if (tls_ver_max < TLS1_1_VERSION)
+    {
+        sslopt |= SSL_OP_NO_TLSv1_1;
+    }
+#endif
+#ifdef SSL_OP_NO_TLSv1_2
+    if (tls_ver_max < TLS1_2_VERSION)
+    {
+        sslopt |= SSL_OP_NO_TLSv1_2;
+    }
+#endif
+    SSL_CTX_set_options(ctx, sslopt);
+}
+#endif /* SSL_CTX_set_max_proto_version */
+
 #endif /* OPENSSL_COMPAT_H_ */
diff --git a/src/openvpn/ssl.c b/src/openvpn/ssl.c
index 7b428455..6c27050f 100644
--- a/src/openvpn/ssl.c
+++ b/src/openvpn/ssl.c
@@ -622,7 +622,10 @@ init_ssl(const struct options *options, struct tls_root_ctx *new_ctx)
      * cipher restrictions before loading certificates */
     tls_ctx_restrict_ciphers(new_ctx, options->cipher_list);
 
-    tls_ctx_set_options(new_ctx, options->ssl_flags);
+    if (!tls_ctx_set_options(new_ctx, options->ssl_flags))
+    {
+        goto err;
+    }
 
     if (options->pkcs12_file)
     {
diff --git a/src/openvpn/ssl_backend.h b/src/openvpn/ssl_backend.h
index 7cf5d830..444fb2f9 100644
--- a/src/openvpn/ssl_backend.h
+++ b/src/openvpn/ssl_backend.h
@@ -162,8 +162,10 @@ bool tls_ctx_initialised(struct tls_root_ctx *ctx);
  *
  * @param ctx           TLS context to set options on
  * @param ssl_flags     SSL flags to set
+ *
+ * @return true on success, false otherwise.
  */
-void tls_ctx_set_options(struct tls_root_ctx *ctx, unsigned int ssl_flags);
+bool tls_ctx_set_options(struct tls_root_ctx *ctx, unsigned int ssl_flags);
 
 /**
  * Restrict the list of ciphers that can be used within the TLS context.
diff --git a/src/openvpn/ssl_mbedtls.c b/src/openvpn/ssl_mbedtls.c
index 8ac52d55..d503162a 100644
--- a/src/openvpn/ssl_mbedtls.c
+++ b/src/openvpn/ssl_mbedtls.c
@@ -206,9 +206,10 @@ key_state_export_keying_material(struct key_state_ssl *ssl,
 {
 }
 
-void
+bool
 tls_ctx_set_options(struct tls_root_ctx *ctx, unsigned int ssl_flags)
 {
+    return true;
 }
 
 static const char *
diff --git a/src/openvpn/ssl_openssl.c b/src/openvpn/ssl_openssl.c
index 86318d4c..50d68280 100644
--- a/src/openvpn/ssl_openssl.c
+++ b/src/openvpn/ssl_openssl.c
@@ -206,16 +206,65 @@ info_callback(INFO_CALLBACK_SSL_CONST SSL *s, int where, int ret)
 int
 tls_version_max(void)
 {
-#if defined(SSL_OP_NO_TLSv1_2)
+#if defined(TLS1_2_VERSION) || defined(SSL_OP_NO_TLSv1_2)
     return TLS_VER_1_2;
-#elif defined(SSL_OP_NO_TLSv1_1)
+#elif defined(TLS1_1_VERSION) || defined(SSL_OP_NO_TLSv1_1)
     return TLS_VER_1_1;
 #else
     return TLS_VER_1_0;
 #endif
 }
 
-void
+/** Convert internal version number to openssl version number */
+static int
+openssl_tls_version(int ver)
+{
+    if (ver == TLS_VER_1_0)
+    {
+        return TLS1_VERSION;
+    }
+    else if (ver == TLS_VER_1_1)
+    {
+        return TLS1_1_VERSION;
+    }
+    else if (ver == TLS_VER_1_2)
+    {
+        return TLS1_2_VERSION;
+    }
+    return 0;
+}
+
+static bool
+tls_ctx_set_tls_versions(struct tls_root_ctx *ctx, unsigned int ssl_flags)
+{
+    int tls_ver_min = openssl_tls_version(
+        (ssl_flags >> SSLF_TLS_VERSION_MIN_SHIFT) & SSLF_TLS_VERSION_MIN_MASK);
+    int tls_ver_max = openssl_tls_version(
+        (ssl_flags >> SSLF_TLS_VERSION_MAX_SHIFT) & SSLF_TLS_VERSION_MAX_MASK);
+
+    if (!tls_ver_min)
+    {
+        /* Enforce at least TLS 1.0 */
+        int cur_min = SSL_CTX_get_min_proto_version(ctx->ctx);
+        tls_ver_min = cur_min < TLS1_VERSION ? TLS1_VERSION : cur_min;
+    }
+
+    if (!SSL_CTX_set_min_proto_version(ctx->ctx, tls_ver_min))
+    {
+        msg(D_TLS_ERRORS, "%s: failed to set minimum TLS version", __func__);
+        return false;
+    }
+
+    if (tls_ver_max && !SSL_CTX_set_max_proto_version(ctx->ctx, tls_ver_max))
+    {
+        msg(D_TLS_ERRORS, "%s: failed to set maximum TLS version", __func__);
+        return false;
+    }
+
+    return true;
+}
+
+bool
 tls_ctx_set_options(struct tls_root_ctx *ctx, unsigned int ssl_flags)
 {
     ASSERT(NULL != ctx);
@@ -223,41 +272,18 @@ tls_ctx_set_options(struct tls_root_ctx *ctx, unsigned int ssl_flags)
     /* default certificate verification flags */
     int flags = SSL_VERIFY_PEER | SSL_VERIFY_FAIL_IF_NO_PEER_CERT;
 
-    /* process SSL options including minimum TLS version we will accept from peer */
-    {
-        long sslopt = SSL_OP_SINGLE_DH_USE | SSL_OP_NO_TICKET | SSL_OP_NO_SSLv2 | SSL_OP_NO_SSLv3;
-        int tls_ver_max = TLS_VER_UNSPEC;
-        const int tls_ver_min =
-            (ssl_flags >> SSLF_TLS_VERSION_MIN_SHIFT) & SSLF_TLS_VERSION_MIN_MASK;
-
-        tls_ver_max =
-            (ssl_flags >> SSLF_TLS_VERSION_MAX_SHIFT) & SSLF_TLS_VERSION_MAX_MASK;
-        if (tls_ver_max <= TLS_VER_UNSPEC)
-        {
-            tls_ver_max = tls_version_max();
-        }
-
-        if (tls_ver_min > TLS_VER_1_0 || tls_ver_max < TLS_VER_1_0)
-        {
-            sslopt |= SSL_OP_NO_TLSv1;
-        }
-#ifdef SSL_OP_NO_TLSv1_1
-        if (tls_ver_min > TLS_VER_1_1 || tls_ver_max < TLS_VER_1_1)
-        {
-            sslopt |= SSL_OP_NO_TLSv1_1;
-        }
-#endif
-#ifdef SSL_OP_NO_TLSv1_2
-        if (tls_ver_min > TLS_VER_1_2 || tls_ver_max < TLS_VER_1_2)
-        {
-            sslopt |= SSL_OP_NO_TLSv1_2;
-        }
-#endif
+    /* process SSL options */
+    long sslopt = SSL_OP_SINGLE_DH_USE | SSL_OP_NO_TICKET;
 #ifdef SSL_OP_CIPHER_SERVER_PREFERENCE
-        sslopt |= SSL_OP_CIPHER_SERVER_PREFERENCE;
+    sslopt |= SSL_OP_CIPHER_SERVER_PREFERENCE;
 #endif
-        sslopt |= SSL_OP_NO_COMPRESSION;
-        SSL_CTX_set_options(ctx->ctx, sslopt);
+    sslopt |= SSL_OP_NO_COMPRESSION;
+
+    SSL_CTX_set_options(ctx->ctx, sslopt);
+
+    if (!tls_ctx_set_tls_versions(ctx, ssl_flags))
+    {
+        return false;
     }
 
 #ifdef SSL_MODE_RELEASE_BUFFERS
@@ -280,6 +306,8 @@ tls_ctx_set_options(struct tls_root_ctx *ctx, unsigned int ssl_flags)
     SSL_CTX_set_verify(ctx->ctx, flags, verify_callback);
 
     SSL_CTX_set_info_callback(ctx->ctx, info_callback);
+
+    return true;
 }
 
 void