How can I use different certificates on specific connections?

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Create an SSLSocket factory yourself, and set it on the HttpsURLConnection before connecting.

...
HttpsURLConnection conn = (HttpsURLConnection)url.openConnection();
conn.setSSLSocketFactory(sslFactory);
conn.setMethod("POST");
...

You’ll want to create one SSLSocketFactory and keep it around. Here’s a sketch of how to initialize it:

/* Load the keyStore that includes self-signed cert as a "trusted" entry. */
KeyStore keyStore = ... 
TrustManagerFactory tmf = 
  TrustManagerFactory.getInstance(TrustManagerFactory.getDefaultAlgorithm());
tmf.init(keyStore);
SSLContext ctx = SSLContext.getInstance("TLS");
ctx.init(null, tmf.getTrustManagers(), null);
sslFactory = ctx.getSocketFactory();

If you need help creating the key store, please comment.

Here’s an example of loading the key store:

KeyStore keyStore = KeyStore.getInstance(KeyStore.getDefaultType());
keyStore.load(trustStore, trustStorePassword);
trustStore.close();

To create the key store with a PEM format certificate, you can write your own code using CertificateFactory, or just import it with keytool from the JDK (keytool won’t work for a “key entry”, but is just fine for a “trusted entry”).

keytool -import -file selfsigned.pem -alias server -keystore server.jks

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