diff --git a/launcher/src/main/java/com/threerings/getdown/launcher/Getdown.java b/launcher/src/main/java/com/threerings/getdown/launcher/Getdown.java
index 503134e..35a6388 100644
--- a/launcher/src/main/java/com/threerings/getdown/launcher/Getdown.java
+++ b/launcher/src/main/java/com/threerings/getdown/launcher/Getdown.java
@@ -38,6 +38,7 @@ import javax.swing.AbstractAction;
 import javax.swing.JButton;
 import javax.swing.JFrame;
 import javax.swing.JLayeredPane;
+import javax.swing.JOptionPane;
 
 import com.samskivert.swing.util.SwingUtil;
 import com.threerings.getdown.data.Application;
@@ -202,11 +203,17 @@ public abstract class Getdown
         _dead = false;
         // if we fail to detect a proxy, but we're allowed to run offline, then go ahead and
         // run the app anyway because we're prepared to cope with not being able to update
-        if (detectProxy() || _app.allowOffline()) getdown();
-        else requestProxyInfo(false);
+        try {
+            if (detectProxy() || _app.allowOffline()) getdown();
+            else requestProxyInfo(false);
+        } catch (IOException ioe) {
+            log.info("Failed to detect if proxy is needed", "error", ioe);
+            log.info("We may need a proxy, or maybe their network is down.");
+            showConnectionFailedDialog();
+        }
     }
 
-    protected boolean detectProxy () {
+    protected boolean detectProxy () throws IOException {
         // first we have to initialize our application to get the appbase URL, etc.
         log.info("Checking whether we need to use a proxy...");
         try {
@@ -223,6 +230,7 @@ public abstract class Getdown
         // see if we actually need a proxy
         updateStatus("m.detecting_proxy");
         URL configURL = _app.getConfigResource().getRemote();
+        // if this detection fails to connect, we'll let the IOException propagate out
         if (!ProxyUtil.canLoadWithoutProxy(configURL, tryNoProxy ? 2 : 5)) {
             // if we didn't auto-detect proxy first thing, do auto-detect now
             return tryNoProxy ? ProxyUtil.autoDetectProxy(_app) : false;
@@ -262,6 +270,33 @@ public abstract class Getdown
         showContainer();
     }
 
+    /**
+     * Shows a dialog informing the user that we could not connect to the download servers,
+     * with buttons to try again or configure a proxy.
+     */
+    protected void showConnectionFailedDialog () {
+        if (_silent) {
+            log.warning("Unable to connect to download servers. Exiting.");
+            return;
+        }
+
+        String message = _msgs.getString("m.proxy_connect_failed");
+        String tryAgain = _msgs.getString("m.try_again");
+        String configureProxy = _msgs.getString("m.configure_proxy_button");
+        Object[] options = { tryAgain, configureProxy };
+        int choice = JOptionPane.showOptionDialog(
+            null, message, "",
+            JOptionPane.YES_NO_OPTION, JOptionPane.WARNING_MESSAGE,
+            null, options, options[0]);
+        if (choice == JOptionPane.YES_OPTION) {
+            // "Try again" — re-run the update/launch sequence
+            run();
+        } else if (choice == JOptionPane.NO_OPTION) {
+            // "Configure proxy" — show the proxy configuration panel
+            requestProxyInfo(false);
+        }
+    }
+
     /**
      * Downloads and installs (without verifying) any resources that are marked with a
      * {@code PRELOAD} attribute.
diff --git a/launcher/src/main/java/com/threerings/getdown/launcher/ProxyUtil.java b/launcher/src/main/java/com/threerings/getdown/launcher/ProxyUtil.java
index 7b69cba..d9849f7 100644
--- a/launcher/src/main/java/com/threerings/getdown/launcher/ProxyUtil.java
+++ b/launcher/src/main/java/com/threerings/getdown/launcher/ProxyUtil.java
@@ -124,35 +124,31 @@ public final class ProxyUtil {
     }
 
     public static boolean canLoadWithoutProxy (URL rurl, int timeoutSeconds)
+      throws IOException
     {
         log.info("Attempting to fetch without proxy: " + rurl);
+        URLConnection conn = Connector.DEFAULT.open(rurl, timeoutSeconds, timeoutSeconds);
+        // if the appbase is not an HTTP/S URL (like file:), then we don't need a proxy
+        if (!(conn instanceof HttpURLConnection)) {
+            return true;
+        }
+        // otherwise, try to make a HEAD request for this URL
+        HttpURLConnection hcon = (HttpURLConnection)conn;
         try {
-            URLConnection conn = Connector.DEFAULT.open(rurl, timeoutSeconds, timeoutSeconds);
-            // if the appbase is not an HTTP/S URL (like file:), then we don't need a proxy
-            if (!(conn instanceof HttpURLConnection)) {
+            hcon.setRequestMethod("HEAD");
+            hcon.connect();
+            // make sure we got a satisfactory response code
+            int rcode = hcon.getResponseCode();
+            if (rcode == HttpURLConnection.HTTP_PROXY_AUTH ||
+                rcode == HttpURLConnection.HTTP_FORBIDDEN) {
+                log.warning("Got an 'HTTP credentials needed' response", "code", rcode);
+                return false;
+            } else {
                 return true;
             }
-            // otherwise, try to make a HEAD request for this URL
-            HttpURLConnection hcon = (HttpURLConnection)conn;
-            try {
-                hcon.setRequestMethod("HEAD");
-                hcon.connect();
-                // make sure we got a satisfactory response code
-                int rcode = hcon.getResponseCode();
-                if (rcode == HttpURLConnection.HTTP_PROXY_AUTH ||
-                    rcode == HttpURLConnection.HTTP_FORBIDDEN) {
-                    log.warning("Got an 'HTTP credentials needed' response", "code", rcode);
-                } else {
-                    return true;
-                }
-            } finally {
-                hcon.disconnect();
-            }
-        } catch (IOException ioe) {
-            log.info("Failed to HEAD " + rurl + ": " + ioe);
-            log.info("We probably need a proxy, but auto-detection failed.");
+        } finally {
+            hcon.disconnect();
         }
-        return false;
     }
 
     public static void configProxy (Application app, String host, String port,
diff --git a/launcher/src/main/resources/com/threerings/getdown/messages.properties b/launcher/src/main/resources/com/threerings/getdown/messages.properties
index 7a33ca0..1b6387a 100644
--- a/launcher/src/main/resources/com/threerings/getdown/messages.properties
+++ b/launcher/src/main/resources/com/threerings/getdown/messages.properties
@@ -11,6 +11,10 @@ m.abort_cancel = Continue installation
 
 m.detecting_proxy = Trying to auto-detect proxy settings
 
+m.proxy_connect_failed = We were unable to connect to the download servers. Please check your Internet connection.
+m.try_again = Try again
+m.configure_proxy_button = Configure proxy
+
 m.configure_proxy = <html>We were unable to connect to the application server to download data. \
   <p> Please make sure that no virus scanner or firewall is blocking network communication with \
   the server. \