diff --git a/src/simplewallet/simplewallet.cpp b/src/simplewallet/simplewallet.cpp
index af8d7526d..e88421fb0 100644
--- a/src/simplewallet/simplewallet.cpp
+++ b/src/simplewallet/simplewallet.cpp
@@ -4196,7 +4196,22 @@ bool simple_wallet::init(const boost::program_options::variables_map& vm)
   }
 
   if (!m_wallet->is_trusted_daemon())
-    message_writer() << (boost::format(tr("Warning: using an untrusted daemon at %s, privacy will be lessened")) % m_wallet->get_daemon_address()).str();
+  {
+    message_writer(console_color_red, true) << (boost::format(tr("Warning: using an untrusted daemon at %s")) % m_wallet->get_daemon_address()).str();
+    message_writer(console_color_red, true) << boost::format(tr("Using a third party daemon can be detrimental to your security and privacy"));
+    bool ssl = false;
+    if (m_wallet->check_connection(NULL, &ssl) && !ssl)
+      message_writer(console_color_red, true) << boost::format(tr("Using your own without SSL exposes your RPC traffic to monitoring"));
+    message_writer(console_color_red, true) << boost::format(tr("You are strongly encouraged to connect to the Monero network using your own daemon"));
+    message_writer(console_color_red, true) << boost::format(tr("If you or someone you trust are operating this daemon, you can use --trusted-daemon"));
+
+    COMMAND_RPC_GET_INFO::request req;
+    COMMAND_RPC_GET_INFO::response res;
+    bool r = m_wallet->invoke_http_json("/get_info", req, res);
+    std::string err = interpret_rpc_response(r, res.status);
+    if (r && err.empty() && (res.was_bootstrap_ever_used || !res.bootstrap_daemon_address.empty()))
+      message_writer(console_color_red, true) << boost::format(tr("Moreover, a daemon is also less secure when running in bootstrap mode"));
+  }
 
   if (m_wallet->get_ring_database().empty())
     fail_msg_writer() << tr("Failed to initialize ring database: privacy enhancing features will be inactive");