I just started with gocd and I am trying to connect agent to server.  I am 
running into the same issue you ran into (log pasted below).
I am using ec2 instances for both server and agent.  I tried start agent on 
the same host as the server first, which was failing with the same error.
So, I tried starting agent on different ec2, still getting the same error.

I also tried the suggestion of removing keystore and restarting the server.
I didnot find guid.txt or agent.jks in /var/lib/go-agent folder or its 
subfolder.

Since this thread is an year old, so I thought of checking if you were able 
to find any resolution.

2017-10-05 21:52:31,885 ERROR [main] ServerBinaryDownloader:80 - Couldn't 
update admin/agent-launcher.jar. Sleeping for 1m. Error:
javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
        at 
sun.security.ssl.InputRecord.handleUnknownRecord(InputRecord.java:710)
        at sun.security.ssl.InputRecord.read(InputRecord.java:527)
        at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:983)
        at 
sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1385)
        at 
sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1413)
        at 
sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1397)
        at 
org.apache.http.conn.ssl.SSLConnectionSocketFactory.createLayeredSocket(SSLConnectionSocketFactory.java:394)
        at 
org.apache.http.conn.ssl.SSLConnectionSocketFactory.connectSocket(SSLConnectionSocketFactory.java:353)
        at 
org.apache.http.impl.conn.DefaultHttpClientConnectionOperator.connect(DefaultHttpClientConnectionOperator.java:141)
        at 
org.apache.http.impl.conn.PoolingHttpClientConnectionManager.connect(PoolingHttpClientConnectionManager.java:353)
        at 
org.apache.http.impl.execchain.MainClientExec.establishRoute(MainClientExec.java:380)
        at 
org.apache.http.impl.execchain.MainClientExec.execute(MainClientExec.java:236)
        at 
org.apache.http.impl.execchain.ProtocolExec.execute(ProtocolExec.java:184)
        at 
org.apache.http.impl.execchain.RetryExec.execute(RetryExec.java:88)
        at 
org.apache.http.impl.execchain.RedirectExec.execute(RedirectExec.java:110)
        at 
org.apache.http.impl.client.InternalHttpClient.doExecute(InternalHttpClient.java:184)
        at 
org.apache.http.impl.client.CloseableHttpClient.execute(CloseableHttpClient.java:82)
        at 
org.apache.http.impl.client.CloseableHttpClient.execute(CloseableHttpClient.java:107)
        at 
com.thoughtworks.go.agent.launcher.ServerBinaryDownloader.fetchUpdateCheckHeaders(ServerBinaryDownloader.java:96)
        at 
com.thoughtworks.go.agent.launcher.ServerBinaryDownloader.downloadIfNecessary(ServerBinaryDownloader.java:72)
        at 
com.thoughtworks.go.agent.launcher.AgentLauncherImpl.launch(AgentLauncherImpl.java:79)
        at 
com.thoughtworks.go.agent.bootstrapper.AgentBootstrapper.go(AgentBootstrapper.java:84)
        at 
com.thoughtworks.go.agent.bootstrapper.AgentBootstrapper.main(AgentBootstrapper.java:65)
        at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
        at 
sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62)
        at 
sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
        at java.lang.reflect.Method.invoke(Method.java:498)
        at com.thoughtworks.gocd.Boot.run(Boot.java:58)
        at com.thoughtworks.gocd.Boot.main(Boot.java:42)

Thank You,
Ranjith

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