openssl s_client using a proxy

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openssl s_client -connect some.https.server:443 -showcerts

is a nice command to run when you want to inspect the server's certificates and its certificate chain.

Is there a way to run this command when you are behind a HTTP/HTTPS proxy ?

openssl
5 Answers

Even with openssl v1.1.0 I had some problems passing our proxy, e.g. s_client: HTTP CONNECT failed: 400 Bad Request That forced me to write a minimal Java-class to show the SSL-Handshake 

    public static void main(String[] args) throws IOException, URISyntaxException {
    HttpHost proxy = new HttpHost("proxy.my.company", 8080);
    DefaultProxyRoutePlanner routePlanner = new DefaultProxyRoutePlanner(proxy);
    CloseableHttpClient httpclient = HttpClients.custom()
            .setRoutePlanner(routePlanner)
            .build();
    URI uri = new URIBuilder()
            .setScheme("https")
            .setHost("www.myhost.com")
            .build();
    HttpGet httpget = new HttpGet(uri);
    httpclient.execute(httpget);
}

With following dependency:

    <dependency>
        <groupId>org.apache.httpcomponents</groupId>
        <artifactId>httpclient</artifactId>
        <version>4.5.2</version>
        <type>jar</type>
    </dependency>

you can run it with Java SSL Logging turned on

This should produce nice output like

trustStore provider is :
init truststore
adding as trusted cert:
  Subject: CN=Equifax Secure Global eBusiness CA-1, O=Equifax Secure Inc., C=US
  Issuer:  CN=Equifax Secure Global eBusiness CA-1, O=Equifax Secure Inc., C=US
  Algorithm: RSA; Serial number: 0xc3517
  Valid from Mon Jun 21 06:00:00 CEST 1999 until Mon Jun 22 06:00:00 CEST 2020

adding as trusted cert:
  Subject: CN=SecureTrust CA, O=SecureTrust Corporation, C=US
  Issuer:  CN=SecureTrust CA, O=SecureTrust Corporation, C=US
(....)
user_49949310
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