{"ok":true,"result":{"url":" https://xx.xx:8443/test/pagebot","has_custom_certificate":false,"pending_update_count":0,"last_error_date":1607191491,"last_error_message":"SSL  error {error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed}","max_connections":40,"ip_address":"........."}}

если генерировать сертификат openssl'ем, то при указании названия организации указываем IP адрес и тогда все ок

routines:SSL_CTX_check_private_key:no certificate assigned

"SSL error {error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed}"

            String[] commands =  new String[] {"curl", "-X", "POST", "-F", "\"url=https://xxx.xxx.xxx.xxx:8443/test/pagebot\"", "-F", "\"certificate=@xcv.pem\"", "\"https://api.telegram.org/botTOKEN/setwebhook\""};
            System.out.println(Arrays.toString(commands));
            Process process = Runtime.getRuntime().exec(commands);
            System.out.println( process.info().toString());
            BufferedReader reader = new BufferedReader(new InputStreamReader(process.getInputStream()));
            String line;
            StringBuilder response = new StringBuilder();
            while ((line = reader.readLine()) != null) {
                response.append(line);
            }

[user: Optional[root], cmd: /usr/bin/curl, args: [-X, POST, -F "url=https://xx.xx.xx.xx:8443/test/pagebot", -F "certificate=/etc/apache2/ssl/@xcv.pem", " https://api.telegram.org/botNOKEN/setwebhook%22%5D]https://api.telegram.org/botNOKEN/setwebhook"],  startTime: Optional[2020-12-06T20:26:27.560Z], totalTime: Optional[PT0S]]

"SSL error {error:14095044:SSL routines:ssl3_read_n:internal error}"

            String[] commands =  new String[] {"curl",  "-F", "url=https://xx.xx.xx.xx:8443/test/pagebot", "-F", "certificate=@/etc/apache2/ssl/xcv.pem", "-F" ,"ip_address=xx.xx.xx.xx", "https://api.telegram.org/botTOKEN/setwebhook"};
            Process process = Runtime.getRuntime().exec(commands);
            System.out.println(process.info().toString());
            BufferedReader reader = new BufferedReader(new InputStreamReader(process.getInputStream()));
            String line;
            StringBuilder response = new StringBuilder();
            while ((line = reader.readLine()) != null) {
                response.append(line);
            }
            System.out.println(response.toString());

try {
            CloseableHttpClient httpClient = HttpClients.createDefault();
            HttpPost uploadFile = new HttpPost("https://api.telegram.org/botTOKEN/setwebhook");
            MultipartEntityBuilder builder = MultipartEntityBuilder.create();
            builder.addTextBody("url", "https://xx.xx.xx.xx:8443/test/pagebot", ContentType.TEXT_PLAIN);
            builder.addTextBody("ip_address", "xx.xx.xx.xx", ContentType.TEXT_PLAIN);

// This attaches the file to the POST:
            File f = new File(ph+"config/xcv.pem");
            builder.addBinaryBody("certificate", new FileInputStream(f), ContentType.APPLICATION_OCTET_STREAM, f.getName());
            HttpEntity multipart = builder.build();
            uploadFile.setEntity(multipart);
            CloseableHttpResponse response = httpClient.execute(uploadFile);
            HttpEntity responseEntity = response.getEntity();

            int ch;
            StringBuilder sb = new StringBuilder();
            while ((ch = responseEntity.getContent().read()) != -1) {
                sb.append((char) ch);
            }
            System.out.println(sb.toString());
        } catch (FileNotFoundException ex) {
            Logger.getLogger(sendFile.class.getName()).log(Level.SEVERE, null, ex);
        } catch (IOException ex) {
            Logger.getLogger(sendFile.class.getName()).log(Level.SEVERE, null, ex);
        }