diff --git a/communicator/ssh/communicator.go b/communicator/ssh/communicator.go
index f05f6e46e..d1be89e64 100644
--- a/communicator/ssh/communicator.go
+++ b/communicator/ssh/communicator.go
@@ -308,6 +308,12 @@ func (c *comm) reconnect() (err error) {
 		// We don't need to do anything here. We just want select to block until
 		// we connect or timeout.
 	case <-timeoutExceeded:
+		if c.conn != nil {
+			c.conn.Close()
+		}
+		if sshConn != nil {
+			sshConn.Close()
+		}
 		return ErrHandshakeTimeout
 	}
 
diff --git a/communicator/ssh/communicator_test.go b/communicator/ssh/communicator_test.go
index 6398bd713..b0bc03508 100644
--- a/communicator/ssh/communicator_test.go
+++ b/communicator/ssh/communicator_test.go
@@ -111,8 +111,8 @@ func newMockBrokenServer(t *testing.T) string {
 		defer c.Close()
 		// This should block for a period of time longer than our timeout in
 		// the test case. That way we invoke a failure scenario.
-		time.Sleep(5 * time.Second)
 		t.Log("Block on handshaking for SSH connection")
+		time.Sleep(5 * time.Second)
 	}()
 
 	return l.Addr().String()