be more flexible about truncated ASN1 times
[freeradius.git] / src / main / tls.c
index 0670986..6816ce6 100644 (file)
@@ -505,6 +505,7 @@ tls_session_t *tls_new_client_session(TALLOC_CTX *ctx, fr_tls_server_conf_t *con
        talloc_set_destructor(ssn, _tls_session_free);
 
        ssn->ctx = conf->ctx;
+       ssn->mtu = conf->fragment_size;
 
        SSL_CTX_set_mode(ssn->ctx, SSL_MODE_ACCEPT_MOVING_WRITE_BUFFER | SSL_MODE_AUTO_RETRY);
 
@@ -537,6 +538,21 @@ tls_session_t *tls_new_client_session(TALLOC_CTX *ctx, fr_tls_server_conf_t *con
        SSL_set_ex_data(ssn->ssl, FR_TLS_EX_INDEX_SSN, (void *)ssn);
        SSL_set_fd(ssn->ssl, fd);
        ret = SSL_connect(ssn->ssl);
+
+       if (ret < 0) {
+               switch (SSL_get_error(ssn->ssl, ret)) {
+                       default:
+                               break;
+
+
+
+               case SSL_ERROR_WANT_READ:
+               case SSL_ERROR_WANT_WRITE:
+                       ssn->connected = false;
+                       return ssn;
+               }
+       }
+
        if (ret <= 0) {
                tls_error_io_log(NULL, ssn, ret, "Failed in " STRINGIFY(__FUNCTION__) " (SSL_connect)");
                talloc_free(ssn);
@@ -544,8 +560,7 @@ tls_session_t *tls_new_client_session(TALLOC_CTX *ctx, fr_tls_server_conf_t *con
                return NULL;
        }
 
-       ssn->mtu = conf->fragment_size;
-
+       ssn->connected = true;
        return ssn;
 }
 
@@ -823,10 +838,10 @@ static void session_init(tls_session_t *ssn)
 
 static void session_close(tls_session_t *ssn)
 {
-       SSL_set_quiet_shutdown(ssn->ssl, 1);
-       SSL_shutdown(ssn->ssl);
-
        if (ssn->ssl) {
+               SSL_set_quiet_shutdown(ssn->ssl, 1);
+               SSL_shutdown(ssn->ssl);
+
                SSL_free(ssn->ssl);
                ssn->ssl = NULL;
        }
@@ -1189,6 +1204,7 @@ static CONF_PARSER tls_server_config[] = {
        { "allow_expired_crl", FR_CONF_OFFSET(PW_TYPE_BOOLEAN, fr_tls_server_conf_t, allow_expired_crl), NULL },
        { "check_cert_cn", FR_CONF_OFFSET(PW_TYPE_STRING, fr_tls_server_conf_t, check_cert_cn), NULL },
        { "cipher_list", FR_CONF_OFFSET(PW_TYPE_STRING, fr_tls_server_conf_t, cipher_list), NULL },
+       { "cipher_server_preference", FR_CONF_OFFSET(PW_TYPE_BOOLEAN, fr_tls_server_conf_t, cipher_server_preference), NULL },
        { "check_cert_issuer", FR_CONF_OFFSET(PW_TYPE_STRING, fr_tls_server_conf_t, check_cert_issuer), NULL },
        { "require_client_cert", FR_CONF_OFFSET(PW_TYPE_BOOLEAN, fr_tls_server_conf_t, require_client_cert), NULL },
 
@@ -1359,11 +1375,10 @@ static int cbtls_new_session(SSL *ssl, SSL_SESSION *sess)
                blob_len = i2d_SSL_SESSION(sess, NULL);
                if (blob_len < 1) {
                        /* something went wrong */
-                       RWDEBUG("Session serialisation failed, couldn't determine required buffer length");
+                       if (request) RWDEBUG("Session serialisation failed, couldn't determine required buffer length");
                        return 0;
                }
 
-
                /* Do not convert to TALLOC - Thread safety */
                /* alloc and convert to ASN.1 */
                sess_blob = malloc(blob_len);
@@ -1375,26 +1390,39 @@ static int cbtls_new_session(SSL *ssl, SSL_SESSION *sess)
                p = sess_blob;
                rv = i2d_SSL_SESSION(sess, &p);
                if (rv != blob_len) {
-                       RWDEBUG("Session serialisation failed");
+                       if (request) RWDEBUG("Session serialisation failed");
                        goto error;
                }
 
                /* open output file */
                snprintf(filename, sizeof(filename), "%s%c%s.asn1",
                         conf->session_cache_path, FR_DIR_SEP, buffer);
-               fd = open(filename, O_RDWR|O_CREAT|O_EXCL, 0600);
+               fd = open(filename, O_RDWR|O_CREAT|O_EXCL, S_IWUSR);
                if (fd < 0) {
-                       RERROR("Session serialisation failed, failed opening session file %s: %s",
-                             filename, fr_syserror(errno));
+                       if (request) RERROR("Session serialisation failed, failed opening session file %s: %s",
+                                           filename, fr_syserror(errno));
                        goto error;
                }
 
+               /*
+                *      Set the filename to be temporarily write-only.
+                */
+               if (request) {
+                       VALUE_PAIR *vp;
+
+                       vp = fr_pair_afrom_num(request->state_ctx, PW_TLS_CACHE_FILENAME, 0);
+                       if (vp) {
+                               fr_pair_value_strcpy(vp, filename);
+                               fr_pair_add(&request->state, vp);
+                       }
+               }
+
                todo = blob_len;
                p = sess_blob;
                while (todo > 0) {
                        rv = write(fd, p, todo);
                        if (rv < 1) {
-                               RWDEBUG("Failed writing session: %s", fr_syserror(errno));
+                               if (request) RWDEBUG("Failed writing session: %s", fr_syserror(errno));
                                close(fd);
                                goto error;
                        }
@@ -1402,7 +1430,7 @@ static int cbtls_new_session(SSL *ssl, SSL_SESSION *sess)
                        todo -= rv;
                }
                close(fd);
-               RWDEBUG("Wrote session %s to %s (%d bytes)", buffer, filename, blob_len);
+               if (request) RWDEBUG("Wrote session %s to %s (%d bytes)", buffer, filename, blob_len);
        }
 
 error:
@@ -1411,7 +1439,73 @@ error:
        return 0;
 }
 
+/** Convert OpenSSL's ASN1_TIME to an epoch time
+ *
+ * @param[out] out     Where to write the time_t.
+ * @param[in] asn1     The ASN1_TIME to convert.
+ * @return
+ *     - 0 success.
+ *     - -1 on failure.
+ */
+static int ocsp_asn1time_to_epoch(time_t *out, char const *asn1)
+{
+       struct          tm t;
+       char const      *p = asn1, *end = p + strlen(p);
+
+       memset(&t, 0, sizeof(t));
+
+       if ((end - p) <= 12) {
+               if ((end - p) < 2) {
+                       fr_strerror_printf("ASN1 date string too short, expected 2 additional bytes, got %zu bytes",
+                                          end - p);
+                       return -1;
+               }
+
+               t.tm_year = (*(p++) - '0') * 10;
+               t.tm_year += (*(p++) - '0');
+               if (t.tm_year < 70) t.tm_year += 100;
+       } else {
+               t.tm_year = (*(p++) - '0') * 1000;
+               t.tm_year += (*(p++) - '0') * 100;
+               t.tm_year += (*(p++) - '0') * 10;
+               t.tm_year += (*(p++) - '0');
+               t.tm_year -= 1900;
+       }
+
+       if ((end - p) < 4) {
+               fr_strerror_printf("ASN1 string too short, expected 10 additional bytes, got %zu bytes",
+                                  end - p);
+               return -1;
+       }
+
+       t.tm_mon = (*(p++) - '0') * 10;
+       t.tm_mon += (*(p++) - '0') - 1; // -1 since January is 0 not 1.
+       t.tm_mday = (*(p++) - '0') * 10;
+       t.tm_mday += (*(p++) - '0');
+
+       if ((end - p) < 2) goto done;
+       t.tm_hour = (*(p++) - '0') * 10;
+       t.tm_hour += (*(p++) - '0');
+
+       if ((end - p) < 2) goto done;
+       t.tm_min = (*(p++) - '0') * 10;
+       t.tm_min += (*(p++) - '0');
+
+       if ((end - p) < 2) goto done;
+       t.tm_sec = (*(p++) - '0') * 10;
+       t.tm_sec += (*(p++) - '0');
+
+       /* Apparently OpenSSL converts all timestamps to UTC? Maybe? */
+done:
+       *out = timegm(&t);
+       return 0;
+}
+
+#if OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
 static SSL_SESSION *cbtls_get_session(SSL *ssl, unsigned char *data, int len, int *copy)
+#else
+static SSL_SESSION *cbtls_get_session(SSL *ssl, const unsigned char *data, int len, int *copy)
+#endif
 {
        size_t                  size;
        char                    buffer[2 * MAX_SESSION_SIZE + 1];
@@ -1453,37 +1547,28 @@ static SSL_SESSION *cbtls_get_session(SSL *ssl, unsigned char *data, int len, in
 
                struct stat     st;
                VALUE_PAIR      *vps = NULL;
-
-               /* read in the cached VPs from the .vps file */
-               snprintf(filename, sizeof(filename), "%s%c%s.vps",
-                        conf->session_cache_path, FR_DIR_SEP, buffer);
-               rv = pairlist_read(talloc_ctx, filename, &pairlist, 1);
-               if (rv < 0) {
-                       /* not safe to un-persist a session w/o VPs */
-                       RWDEBUG("Failed loading persisted VPs for session %s", buffer);
-                       goto err;
-               }
+               VALUE_PAIR      *vp;
 
                /* load the actual SSL session */
                snprintf(filename, sizeof(filename), "%s%c%s.asn1", conf->session_cache_path, FR_DIR_SEP, buffer);
                fd = open(filename, O_RDONLY);
                if (fd < 0) {
                        RWDEBUG("No persisted session file %s: %s", filename, fr_syserror(errno));
-                       goto err;
+                       goto error;
                }
 
                rv = fstat(fd, &st);
                if (rv < 0) {
                        RWDEBUG("Failed stating persisted session file %s: %s", filename, fr_syserror(errno));
                        close(fd);
-                       goto err;
+                       goto error;
                }
 
                sess_data = talloc_array(NULL, unsigned char, st.st_size);
                if (!sess_data) {
                        RWDEBUG("Failed allocating buffer for persisted session (%d bytes)", (int) st.st_size);
                        close(fd);
-                       goto err;
+                       goto error;
                }
 
                q = sess_data;
@@ -1493,7 +1578,7 @@ static SSL_SESSION *cbtls_get_session(SSL *ssl, unsigned char *data, int len, in
                        if (rv < 1) {
                                RWDEBUG("Failed reading persisted session: %s", fr_syserror(errno));
                                close(fd);
-                               goto err;
+                               goto error;
                        }
                        todo -= rv;
                        q += rv;
@@ -1516,7 +1601,53 @@ static SSL_SESSION *cbtls_get_session(SSL *ssl, unsigned char *data, int len, in
                sess = d2i_SSL_SESSION(NULL, o, st.st_size);
                if (!sess) {
                        RWDEBUG("Failed loading persisted session: %s", ERR_error_string(ERR_get_error(), NULL));
-                       goto err;
+                       goto error;
+               }
+
+               /* read in the cached VPs from the .vps file */
+               snprintf(filename, sizeof(filename), "%s%c%s.vps",
+                        conf->session_cache_path, FR_DIR_SEP, buffer);
+               rv = pairlist_read(talloc_ctx, filename, &pairlist, 1);
+               if (rv < 0) {
+                       /* not safe to un-persist a session w/o VPs */
+                       RWDEBUG("Failed loading persisted VPs for session %s", buffer);
+                       SSL_SESSION_free(sess);
+                       sess = NULL;
+                       goto error;
+               }
+
+               /*
+                *      Enforce client certificate expiration.
+                */
+               vp = fr_pair_find_by_num(pairlist->reply, PW_TLS_CLIENT_CERT_EXPIRATION, 0, TAG_ANY);
+               if (vp) {
+                       time_t expires;
+
+                       if (ocsp_asn1time_to_epoch(&expires, vp->vp_strvalue) < 0) {
+                               RDEBUG2("Failed getting certificate expiration, removing cache entry for session %s - %s", buffer, fr_strerror());
+                               SSL_SESSION_free(sess);
+                               sess = NULL;
+                               goto error;
+                       }
+
+                       if (expires <= request->timestamp) {
+                               RDEBUG2("Certificate has expired, removing cache entry for session %s", buffer);
+                               SSL_SESSION_free(sess);
+                               sess = NULL;
+                               goto error;
+                       }
+
+                       /*
+                        *      Account for Session-Timeout, if it's available.
+                        */
+                       vp = fr_pair_find_by_num(request->reply->vps, PW_SESSION_TIMEOUT, 0, TAG_ANY);
+                       if (vp) {
+                               if ((request->timestamp + vp->vp_integer) > expires) {
+                                       vp->vp_integer = expires - request->timestamp;
+                                       RWDEBUG2("Updating Session-Timeout to %u, due to impending certificate expiration",
+                                                vp->vp_integer);
+                               }
+                       }
                }
 
                /* move the cached VPs into the session */
@@ -1526,7 +1657,7 @@ static SSL_SESSION *cbtls_get_session(SSL *ssl, unsigned char *data, int len, in
                RWDEBUG("Successfully restored session %s", buffer);
                rdebug_pair_list(L_DBG_LVL_2, request, vps, "reply:");
        }
-err:
+error:
        if (sess_data) talloc_free(sess_data);
        if (pairlist) pairlist_free(&pairlist);
 
@@ -1910,8 +2041,11 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
        char            cn_str[1024];
        char            buf[64];
        X509            *client_cert;
-       X509_CINF       *client_inf;
+#if OPENSSL_VERSION_NUMBER >= 0x10100000L && !defined(LIBRESSL_VERSION_NUMBER)
+       const STACK_OF(X509_EXTENSION) *ext_list;
+#else
        STACK_OF(X509_EXTENSION) *ext_list;
+#endif
        SSL             *ssl;
        int             err, depth, lookup, loc;
        fr_tls_server_conf_t *conf;
@@ -2016,7 +2150,7 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
                rdebug_pair(L_DBG_LVL_2, request, vp, NULL);
        }
 
-       X509_NAME_oneline(X509_get_issuer_name(ctx->current_cert), issuer,
+       X509_NAME_oneline(X509_get_issuer_name(client_cert), issuer,
                          sizeof(issuer));
        issuer[sizeof(issuer) - 1] = '\0';
        if (certs && identity && (lookup <= 1) && issuer[0]) {
@@ -2038,7 +2172,7 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
        /*
         *      Get the RFC822 Subject Alternative Name
         */
-       loc = X509_get_ext_by_NID(client_cert, NID_subject_alt_name, 0);
+       loc = X509_get_ext_by_NID(client_cert, NID_subject_alt_name, -1);
        if (certs && (lookup <= 1) && (loc >= 0)) {
                X509_EXTENSION *ext = NULL;
                GENERAL_NAMES *names = NULL;
@@ -2053,14 +2187,14 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
 #ifdef GEN_EMAIL
                                case GEN_EMAIL:
                                        vp = fr_pair_make(talloc_ctx, certs, cert_attr_names[FR_TLS_SAN_EMAIL][lookup],
-                                                     (char *) ASN1_STRING_data(name->d.rfc822Name), T_OP_SET);
+                                                     (char const *) ASN1_STRING_get0_data(name->d.rfc822Name), T_OP_SET);
                                        rdebug_pair(L_DBG_LVL_2, request, vp, NULL);
                                        break;
 #endif /* GEN_EMAIL */
 #ifdef GEN_DNS
                                case GEN_DNS:
                                        vp = fr_pair_make(talloc_ctx, certs, cert_attr_names[FR_TLS_SAN_DNS][lookup],
-                                                     (char *) ASN1_STRING_data(name->d.dNSName), T_OP_SET);
+                                                     (char const *) ASN1_STRING_get0_data(name->d.dNSName), T_OP_SET);
                                        rdebug_pair(L_DBG_LVL_2, request, vp, NULL);
                                        break;
 #endif /* GEN_DNS */
@@ -2071,7 +2205,7 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
                                            /* we've got a UPN - Must be ASN1-encoded UTF8 string */
                                            if (name->d.otherName->value->type == V_ASN1_UTF8STRING) {
                                                    vp = fr_pair_make(talloc_ctx, certs, cert_attr_names[FR_TLS_SAN_UPN][lookup],
-                                                                 (char *) ASN1_STRING_data(name->d.otherName->value->value.utf8string), T_OP_SET);
+                                                                 (char const *) ASN1_STRING_get0_data(name->d.otherName->value->value.utf8string), T_OP_SET);
                                                    rdebug_pair(L_DBG_LVL_2, request, vp, NULL);
                                                break;
                                            } else {
@@ -2088,7 +2222,7 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
                        }
                }
                if (names != NULL)
-                       sk_GENERAL_NAME_free(names);
+                       GENERAL_NAMES_free(names);
        }
 
        /*
@@ -2109,8 +2243,13 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
        }
 
        if (lookup == 0) {
+#if OPENSSL_VERSION_NUMBER >= 0x10100000L && !defined(LIBRESSL_VERSION_NUMBER)
+               ext_list = X509_get0_extensions(client_cert);
+#else
+               X509_CINF       *client_inf;
                client_inf = client_cert->cert_info;
                ext_list = client_inf->extensions;
+#endif
        } else {
                ext_list = NULL;
        }
@@ -2170,7 +2309,7 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
 
        REXDENT();
 
-       switch (ctx->error) {
+       switch (X509_STORE_CTX_get_error(ctx)) {
        case X509_V_ERR_UNABLE_TO_GET_ISSUER_CERT:
                RERROR("issuer=%s", issuer);
                break;
@@ -2313,7 +2452,8 @@ int cbtls_verify(int ok, X509_STORE_CTX *ctx)
                                                true, true, EXEC_TIMEOUT) != 0) {
                                AUTH(LOG_PREFIX ": Certificate CN (%s) fails external verification!", common_name);
                                my_ok = 0;
-                       } else {
+
+                       } else  if (request) {
                                RDEBUG("Client certificate CN %s passed external validation", common_name);
                        }
 
@@ -2418,27 +2558,27 @@ static int set_ecdh_curve(SSL_CTX *ctx, char const *ecdh_curve, bool disable_sin
  * is using the session
  */
 static void sess_free_vps(UNUSED void *parent, void *data_ptr,
-                               UNUSED CRYPTO_EX_DATA *ad, UNUSED int idx,
-                               UNUSED long argl, UNUSED void *argp)
+                                UNUSED CRYPTO_EX_DATA *ad, UNUSED int idx,
+                                UNUSED long argl, UNUSED void *argp)
 {
-       VALUE_PAIR *vp = data_ptr;
-       if (!vp) return;
+        VALUE_PAIR *vp = data_ptr;
+        if (!vp) return;
 
-       DEBUG2(LOG_PREFIX ": Freeing cached session VPs");
+        DEBUG2(LOG_PREFIX ": Freeing cached session VPs");
 
-       fr_pair_list_free(&vp);
+        fr_pair_list_free(&vp);
 }
 
 static void sess_free_certs(UNUSED void *parent, void *data_ptr,
-                               UNUSED CRYPTO_EX_DATA *ad, UNUSED int idx,
-                               UNUSED long argl, UNUSED void *argp)
+                                UNUSED CRYPTO_EX_DATA *ad, UNUSED int idx,
+                                UNUSED long argl, UNUSED void *argp)
 {
-       VALUE_PAIR **certs = data_ptr;
-       if (!certs) return;
+        VALUE_PAIR **certs = data_ptr;
+        if (!certs) return;
 
-       DEBUG2(LOG_PREFIX ": Freeing cached session Certificates");
+        DEBUG2(LOG_PREFIX ": Freeing cached session Certificates");
 
-       fr_pair_list_free(certs);
+        fr_pair_list_free(certs);
 }
 
 /** Add all the default ciphers and message digests reate our context.
@@ -2451,7 +2591,7 @@ void tls_global_init(void)
        SSL_load_error_strings();       /* readable error messages (examples show call before library_init) */
        SSL_library_init();             /* initialize library */
        OpenSSL_add_all_algorithms();   /* required for SHA2 in OpenSSL < 0.9.8o and 1.0.0.a */
-       OPENSSL_config(NULL);
+       CONF_modules_load_file(NULL, NULL, 0);
 
        /*
         *      Initialize the index for the certificates.
@@ -2483,17 +2623,22 @@ int tls_global_version_check(char const *acknowledged)
                        /*
                         *      If the CVE is acknowledged, allow it.
                         */
-                       if (strcmp(acknowledged, defect->id) == 0) return 0;
+                       if (!bad && (strcmp(acknowledged, defect->id) == 0)) return 0;
 
                        ERROR("Refusing to start with libssl version %s (in range %s)",
                              ssl_version(), ssl_version_range(defect->low, defect->high));
                        ERROR("Security advisory %s (%s)", defect->id, defect->name);
                        ERROR("%s", defect->comment);
 
-                       INFO("Once you have verified libssl has been correctly patched, "
-                            "set security.allow_vulnerable_openssl = '%s'", defect->id);
+                       /*
+                        *      Only warn about the first one...
+                        */
+                       if (!bad) {
+                               INFO("Once you have verified libssl has been correctly patched, "
+                                    "set security.allow_vulnerable_openssl = '%s'", defect->id);
 
-                       bad = true;
+                               bad = true;
+                       }
                }
        }
 
@@ -2508,7 +2653,11 @@ int tls_global_version_check(char const *acknowledged)
  */
 void tls_global_cleanup(void)
 {
+#if OPENSSL_VERSION_NUMBER < 0x10000000L
        ERR_remove_state(0);
+#elif OPENSSL_VERSION_NUMBER < 0x10100000L || defined(LIBRESSL_VERSION_NUMBER)
+       ERR_remove_thread_state(NULL);
+#endif
        ENGINE_cleanup();
        CONF_modules_unload(1);
        ERR_free_strings();
@@ -2800,6 +2949,15 @@ post_ca:
         */
        ctx_options |= SSL_OP_DONT_INSERT_EMPTY_FRAGMENTS;
 
+       if (conf->cipher_server_preference) {
+               /*
+                *      SSL_OP_CIPHER_SERVER_PREFERENCE to follow best practice
+                *      of nowday's TLS: do not allow poorly-selected ciphers from
+                *      client to take preference
+                */
+               ctx_options |= SSL_OP_CIPHER_SERVER_PREFERENCE;
+       }
+
        SSL_CTX_set_options(ctx, ctx_options);
 
        /*
@@ -2890,6 +3048,7 @@ post_ca:
                SSL_CTX_set_verify_depth(ctx, conf->verify_depth);
        }
 
+#ifndef LIBRESSL_VERSION_NUMBER
        /* Load randomness */
        if (conf->random_file) {
                if (!(RAND_load_file(conf->random_file, 1024*10))) {
@@ -2897,6 +3056,7 @@ post_ca:
                        return NULL;
                }
        }
+#endif
 
        /*
         * Set the cipher list if we were told to
@@ -2924,9 +3084,9 @@ post_ca:
                }
 
                /*
-                *      Cache it, and DON'T auto-clear it.
+                *      Cache it, DON'T auto-clear it, and disable the internal OpenSSL session cache.
                 */
-               SSL_CTX_set_session_cache_mode(ctx, SSL_SESS_CACHE_SERVER | SSL_SESS_CACHE_NO_AUTO_CLEAR);
+               SSL_CTX_set_session_cache_mode(ctx, SSL_SESS_CACHE_SERVER | SSL_SESS_CACHE_NO_AUTO_CLEAR | SSL_SESS_CACHE_NO_INTERNAL);
 
                SSL_CTX_set_session_id_context(ctx,
                                               (unsigned char *) conf->session_context_id,
@@ -2972,7 +3132,7 @@ static int _tls_server_conf_free(fr_tls_server_conf_t *conf)
        return 0;
 }
 
-static fr_tls_server_conf_t *tls_server_conf_alloc(TALLOC_CTX *ctx)
+fr_tls_server_conf_t *tls_server_conf_alloc(TALLOC_CTX *ctx)
 {
        fr_tls_server_conf_t *conf;
 
@@ -3014,14 +3174,32 @@ fr_tls_server_conf_t *tls_server_conf_parse(CONF_SECTION *cs)
         */
        if (conf->fragment_size < 100) conf->fragment_size = 100;
 
-       if (!conf->private_key_file) {
-               ERROR(LOG_PREFIX ": TLS Server requires a private key file");
-               goto error;
-       }
+       /*
+        *      Only check for certificate things if we don't have a
+        *      PSK query.
+        */
+#ifdef PSK_MAX_IDENTITY_LEN
+       if (conf->psk_identity) {
+               if (conf->private_key_file) {
+                       WARN(LOG_PREFIX ": Ignoring private key file due to psk_identity being used");
+               }
 
-       if (!conf->certificate_file) {
-               ERROR(LOG_PREFIX ": TLS Server requires a certificate file");
-               goto error;
+               if (conf->certificate_file) {
+                       WARN(LOG_PREFIX ": Ignoring certificate file due to psk_identity being used");
+               }
+
+       } else
+#endif
+       {
+               if (!conf->private_key_file) {
+                       ERROR(LOG_PREFIX ": TLS Server requires a private key file");
+                       goto error;
+               }
+
+               if (!conf->certificate_file) {
+                       ERROR(LOG_PREFIX ": TLS Server requires a certificate file");
+                       goto error;
+               }
        }
 
        /*
@@ -3126,6 +3304,7 @@ fr_tls_server_conf_t *tls_client_conf_parse(CONF_SECTION *cs)
        return conf;
 }
 
+
 int tls_success(tls_session_t *ssn, REQUEST *request)
 {
        VALUE_PAIR *vp, *vps = NULL;
@@ -3203,6 +3382,35 @@ int tls_success(tls_session_t *ssn, REQUEST *request)
                         *      Save the certs in the packet, so that we can see them.
                         */
                        fr_pair_add(&request->packet->vps, fr_pair_list_copy(request->packet, *certs));
+
+                       vp = fr_pair_find_by_num(request->packet->vps, PW_TLS_CLIENT_CERT_EXPIRATION, 0, TAG_ANY);
+                       if (vp) {
+                               time_t expires;
+
+                               if (ocsp_asn1time_to_epoch(&expires, vp->vp_strvalue) < 0) {
+                                       RDEBUG2("Failed getting certificate expiration, removing cache entry for session %s", buffer);
+                                       SSL_CTX_remove_session(ssn->ctx, ssn->ssl_session);
+                                       return -1;
+                               }
+
+                               if (expires <= request->timestamp) {
+                                       RDEBUG2("Certificate has expired, removing cache entry for session %s", buffer);
+                                       SSL_CTX_remove_session(ssn->ctx, ssn->ssl_session);
+                                       return -1;
+                               }
+
+                               /*
+                                *      Account for Session-Timeout, if it's available.
+                                */
+                               vp = fr_pair_find_by_num(request->reply->vps, PW_SESSION_TIMEOUT, 0, TAG_ANY);
+                               if (vp) {
+                                       if ((request->timestamp + vp->vp_integer) > expires) {
+                                               vp->vp_integer = expires - request->timestamp;
+                                               RWDEBUG2("Updating Session-Timeout to %u, due to impending certificate expiration",
+                                                        vp->vp_integer);
+                                       }
+                               }
+                       }
                }
 
                if (vps) {