diff --git a/autopush_rs/src/server/mod.rs b/autopush_rs/src/server/mod.rs
index 09ee633c..5c4b549a 100644
--- a/autopush_rs/src/server/mod.rs
+++ b/autopush_rs/src/server/mod.rs
@@ -462,15 +462,23 @@ impl Future for PingManager {
 
     fn poll(&mut self) -> Poll<(), Error> {
         // If it's time for us to send a ping, then queue up a ping to get sent
-        // and start the clock for that ping to time out.
+        // and start the clock for that ping to time out once the ping is
+        // actually sent out on the socket.
         while let Async::Ready(_) = self.ping_interval.poll()? {
             match self.timeout {
                 TimeoutState::None => {}
                 _ => continue,
             }
+            debug!("scheduling a ping to be sent");
             self.socket.borrow_mut().ping = true;
-            let timeout = Timeout::new(self.srv.opts.auto_ping_timeout, &self.srv.handle)?;
-            self.timeout = TimeoutState::Ping(timeout);
+        }
+        {
+            let mut socket = self.socket.borrow_mut();
+            if socket.ping && socket.send_ping()?.is_ready() {
+                let timeout = Timeout::new(self.srv.opts.auto_ping_timeout,
+                                           &self.srv.handle)?;
+                self.timeout = TimeoutState::Ping(timeout);
+            }
         }
 
         // If the client takes too long to respond to our websocket ping or too
@@ -488,24 +496,33 @@ impl Future for PingManager {
             }
             TimeoutState::Ping(ref mut timeout) => {
                 if timeout.poll()?.is_ready() {
-                    if let CloseState::Exchange(ref mut client) = self.client {
-                        client.shutdown();
-                    }
-                    return Err("pong not received within timeout".into())
+                    // We may not actually be reading messages from the
+                    // websocket right now, could have been waiting on something
+                    // else. Instead of immediately returning an error here wait
+                    // for the stream to return `NotReady` when looking for
+                    // messages, as then we're extra sure that no pong was
+                    // received after this timeout elapsed.
+                    debug!("ping timeout fired, scheduling error to maybe happen");
+                    self.socket.borrow_mut().pong_timeout = true;
+                    // `timeout` is cleared in the clause below
                 }
             }
         }
 
         // Received pongs will clear our ping timeout, but not the close
         // timeout.
-        if self.socket.borrow_mut().poll_pong().is_ready() {
-            if let TimeoutState::Ping(_) = self.timeout {
+        if let TimeoutState::Ping(_) = self.timeout {
+            let mut socket = self.socket.borrow_mut();
+            if socket.poll_pong().is_ready() || socket.pong_timeout {
+                debug!("clearing ping timeout");
                 self.timeout = TimeoutState::None;
             }
         }
 
-        // Ensure the scheduled ping is actually flushed out
-        self.socket.borrow_mut().poll_complete()?;
+        // Be sure to always flush out any buffered messages/pings
+        self.socket.borrow_mut().poll_complete().chain_err(|| {
+            "failed routine `poll_complete` call"
+        })?;
 
         // At this point looks our state of ping management A-OK, so try to
         // make progress on our client, and when done with that execute the
@@ -531,6 +548,7 @@ struct WebpushSocket<T> {
     inner: T,
     pong: Pong,
     ping: bool,
+    pong_timeout: bool,
 }
 
 enum Pong {
@@ -545,6 +563,7 @@ impl<T> WebpushSocket<T> {
             inner: t,
             pong: Pong::None,
             ping: false,
+            pong_timeout: false,
         }
     }
 
@@ -554,6 +573,7 @@ impl<T> WebpushSocket<T> {
             Pong::Received => return Async::Ready(()),
             Pong::Waiting(_) => {}
         }
+        debug!("waiting for a pong");
         self.pong = Pong::Waiting(task::current());
         Async::NotReady
     }
@@ -562,9 +582,16 @@ impl<T> WebpushSocket<T> {
         where T: Sink<SinkItem = Message>, Error: From<T::SinkError>
     {
         if self.ping {
+            debug!("sending a ping");
             match self.inner.start_send(Message::Ping(Vec::new()))? {
-                AsyncSink::Ready => self.ping = false,
-                AsyncSink::NotReady(_) => return Ok(Async::NotReady),
+                AsyncSink::Ready => {
+                    debug!("ping sent");
+                    self.ping = false;
+                }
+                AsyncSink::NotReady(_) => {
+                    debug!("ping not ready to be sent");
+                    return Ok(Async::NotReady)
+                }
             }
         }
         Ok(Async::Ready(()))
@@ -580,32 +607,46 @@ impl<T> Stream for WebpushSocket<T>
 
     fn poll(&mut self) -> Poll<Option<ClientMessage>, Error> {
         loop {
-            match try_ready!(self.inner.poll()) {
-                Some(Message::Text(ref s)) => {
+            let msg = match self.inner.poll()? {
+                Async::Ready(Some(msg)) => msg,
+                Async::Ready(None) => return Ok(None.into()),
+                Async::NotReady => {
+                    // If we don't have any more messages and our pong timeout
+                    // elapsed (set above) then this is where we start
+                    // triggering errors.
+                    if self.pong_timeout {
+                        return Err("failed to receive a pong in time".into())
+                    }
+                    return Ok(Async::NotReady)
+                }
+            };
+            match msg {
+                Message::Text(ref s) => {
+                    trace!("text message {}", s);
                     let msg = serde_json::from_str(s).chain_err(|| "invalid json text")?;
                     return Ok(Some(msg).into())
                 }
 
-                Some(Message::Binary(_)) => {
+                Message::Binary(_) => {
                     return Err("binary messages not accepted".into())
                 }
 
                 // sending a pong is already managed by lower layers, just go to
                 // the next message
-                Some(Message::Ping(_)) => {}
+                Message::Ping(_) => {}
 
                 // Wake up tasks waiting for a pong, if any.
-                Some(Message::Pong(_)) => {
+                Message::Pong(_) => {
+                    self.pong_timeout = false;
                     match mem::replace(&mut self.pong, Pong::Received) {
                         Pong::None => {}
                         Pong::Received => {}
                         Pong::Waiting(task) => {
+                            debug!("notifying a task of a pong");
                             task.notify();
                         }
                     }
                 }
-
-                None => return Ok(None.into()),
             }
         }
     }