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answers:

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I want to write a quick server app in Sinatra. It has to be self-contained (i.e. not use apache/nginx/passenger) but also has to support SSL.

Is there an easy way to enable SSL support for Sinatra (using WEBRick for example)?

A: 

Use JRuby interpreter + jetty-rackup gem (http://github.com/geekq/jetty-rackup) Edit jetty-rackup file in the jetty-rackup gem and add a SslSocketConnector, some code to help you:

    security_connector = Jetty::Security::SslSocketConnector.new
    security_connector.set_acceptors(config[:acceptor_size])
    security_connector.port = config[:port]
    security_connector.confidential_port = config[:port]
    security_connector.keystore = keystore
    security_connector.password = config[:password]
    security_connector.key_password = config[:key_password].nil? ? config[:password] : config[:key_password]
    security_connector.truststore = truststore
    security_connector.trust_password = config[:trust_pasword].nil? ? config[:password] : config[:trust_pasword]
    server.add_connector(security_connector)

Sample config:

# Config
:acceptor_size: 10
:ssl: true
:keystore: keystore.jks
:password: your_pass
# :key_password: your_pass # if different
# :truststore: truststore.jks # if different
# :trust_pasword: your_pass # if different

Generating keystore.jks : http://docs.codehaus.org/display/JETTY/How+to+configure+SSL

clyfe