diff --git a/tools/inspector.js b/tools/inspector.js
index 8cb39b51b8..889d95111f 100644
--- a/tools/inspector.js
+++ b/tools/inspector.js
@@ -1,15 +1,110 @@
 var assert = require("assert");
+var net = require("net");
 var inspector = require("node-inspector");
-var inspectorBinPath = require.resolve("node-inspector/bin/inspector");
 var spawn = require("child_process").spawn;
+var _ = require("underscore");
 var chalk = require("chalk");
 var EOL = require("os").EOL;
-var debugPortToProcess = [];
-var hasOwn = Object.prototype.hasOwnProperty;
+var Protocol = require("_debugger").Protocol;
+var debugEntries = [];
 
-function start(debugPort) {
+// There can be only one debugger attached to a process at a time, and
+// detaching can leave the child process in a weird state for future
+// debugging, so the code that attaches to the child process must also
+// serve as a proxy for connections from actual debugger clients like
+// node-inspector.
+
+// This proxying system requires the child process to be invoked with
+// --debug-brk=<port> where <port> is not the same as debugPort, so that
+// we can proxy data between <port> and debugPort, as if the child process
+// were listening on debugPort (as it did before this commit).
+
+// The first time the server starts, the --debug-brk behavior of pausing
+// at the first line of the program is helpful so that the user can set
+// breakpoints. When the server restarts, however, that behavior is more
+// confusing than helpful, especially since the server can restart
+// multiple times in quick succession if the user edits and saves a file
+// multiple times. To avoid this confusion, we use the proxy to send a
+// continue command to resume execution automatically after restart.
+
+// Itercepting debugger requests, responses, events, etc. has the
+// additional benefit of allowing us to print helpful information to the
+// console, like notifying the developer that the debugger hit a
+// breakpoint, so that there is less confusion when the app is not
+// responding to requests.
+
+function start(debugPort, entryPoint) {
   debugPort = +(debugPort || 5858);
 
+  var entry = debugEntries[debugPort];
+  if (entry instanceof DebugEntry) {
+    return entry.attach;
+  }
+
+  debugEntries[debugPort] = entry =
+    new DebugEntry(debugPort, entryPoint);
+
+  return entry.attach;
+}
+
+function DebugEntry(debugPort, entryPoint) {
+  assert.ok(this instanceof DebugEntry);
+
+  this.debugPort = debugPort;
+  this.entryPoint = entryPoint;
+  this.incomingSink = new BackloggedStreamWriter;
+  this.outgoingSink = new BackloggedStreamWriter;
+  this.inspectorProcess = null;
+  this.interceptServer = null;
+  this.debugConnection = null;
+  this.connectCount = 0;
+  this.attach = this.attach.bind(this);
+
+  // We create a connection to whatever port the child process says it's
+  // listening on, so this port is purely advisory.
+  this.attach.suggestedDebugBrkPort = debugPort + 101;
+}
+
+var DEp = DebugEntry.prototype;
+
+DEp.attach = function attach(child) {
+  this.incomingSink.clear();
+  this.outgoingSink.clear();
+
+  this.startInterceptServer();
+  this.startInspector();
+  this.connectToChildProcess(child);
+};
+
+// The intercept server listens for connections and data from
+// node-inspector (on debugPort) and mediates communication between
+// node-inspector and the child process that we're debugging, so that we
+// can inject our own commands (e.g. "continue") and print helpful
+// information to the console when the debugger hits breakpoints. Note
+// that the intercept server survives server restarts, just like
+// node-inspector.
+DEp.startInterceptServer = function startInterceptServer() {
+  var self = this;
+  if (self.interceptServer) {
+    return;
+  }
+
+  self.interceptServer = net.createServer(function(socket) {
+    self.outgoingSink.setTarget(socket);
+    socket.on("data", function(buffer) {
+      self.incomingSink.write(buffer);
+    });
+  }).on("error", function(err) {
+    self.interceptServer = null;
+  }).listen(self.debugPort);
+};
+
+DEp.startInspector = function startInspector() {
+  var self = this;
+  if (self.inspectorProcess) {
+    return;
+  }
+
   // Port 8080 is the default port that node-inspector uses for its web
   // server, and port 5858 is the default port that node listens on when
   // it receives the --debug or --debug-brk flags. Developers familiar
@@ -17,23 +112,16 @@ function start(debugPort) {
   // saved in their browser history already, so let's stick with these
   // conventions in the default case (unless of course the developer runs
   // `meteor debug --debug-port <some other port>`).
+  var debugPort = self.debugPort;
   var webPort = 8080 + debugPort - 5858;
 
-  if (hasOwn.call(debugPortToProcess, debugPort)) {
-    return debugPortToProcess[debugPort];
-  }
-
   var proc = spawn(process.execPath, [
-    inspectorBinPath,
+    require.resolve("node-inspector/bin/inspector"),
     "--web-port", "" + webPort,
     "--debug-port", "" + debugPort
   ]);
 
-  proc.url = inspector.buildInspectorUrl(
-    "localhost",
-    webPort,
-    debugPort
-  );
+  proc.url = inspector.buildInspectorUrl("localhost", webPort, debugPort);
 
   // Forward error output to process.stderr, but silence normal output.
   // proc.stdout.pipe(process.stdout);
@@ -41,20 +129,167 @@ function start(debugPort) {
 
   proc.on("exit", function(code) {
     // Restart the process if it died without us explicitly stopping it.
-    if (debugPortToProcess[debugPort] === proc) {
-      delete debugPortToProcess[debugPort];
-      start(debugPort);
+    if (self.inspectorProcess === proc) {
+      self.inspectorProcess = null;
+      self.startInspector();
     }
   });
 
-  debugPortToProcess[debugPort] = proc;
+  self.inspectorProcess = proc;
+};
 
-  return proc;
+DEp.connectToChildProcess = function connectToChildProcess(child) {
+  var self = this;
+
+  // Wait for the child process to tell us it's listening on a certain
+  // port (not debugPort!), and create a connection to that port so that
+  // the child process can communicate with node-inspector.
+  child.stderr.on("data", function onData(buffer) {
+    var match = /debugger listening on port (\d+)/
+      .exec(buffer.toString("utf8"));
+    if (match) {
+      child.stderr.removeListener("data", onData);
+      connect(+match[1]);
+    }
+  });
+
+  function connect(port) {
+    disconnect();
+
+    self.debugConnection = net.createConnection(port);
+    self.debugConnection.setEncoding("utf8");
+    self.debugConnection.on("data", function(buffer) {
+      protocol.execute(buffer);
+      self.outgoingSink.write(buffer);
+    }).on("error", disconnect);
+
+    var protocol = new Protocol;
+    protocol.onResponse = function onResponse(res) {
+      // Listen for break events so that we can either skip them or print
+      // information to the console about them.
+      if (res.body.type === "event" &&
+          res.body.event === "break") {
+        var scriptName = res.body.body.script.name;
+        var lineNumber = res.body.body.sourceLine + 1;
+
+        if (self.connectCount > 1 &&
+            scriptName === self.entryPoint) {
+          // If we've restarted the server at least once and the break
+          // event occurred in the entry point file (typically
+          // .meteor/local/build/main.js), send a continue command to skip
+          // this breakpoint automatically, so that the user does not have
+          // to keep manually continuing the debugger every time the
+          // server restarts.
+          sendContinue();
+
+        } else {
+          // Give some indication in the console that server execution has
+          // stopped at a breakpoint.
+          process.stdout.write(
+            "Paused at " + scriptName + ":" + lineNumber + "\n"
+          );
+        }
+      }
+    };
+
+    var sentContinue = false;
+    function sendContinue() {
+      if (! sentContinue) {
+        sentContinue = true;
+        self.incomingSink.write(protocol.serialize({
+          command: "continue"
+        }));
+      }
+    }
+
+    if (self.connectCount++ === 0) {
+      process.stdout.write(banner(self.debugPort));
+    } else {
+      // Sometimes (for no good reason) the protocol.onResponse handler
+      // never receives a break event at the very beginning of the
+      // program. This timeout races against that break event to make sure
+      // we send exactly one continue command.
+      setTimeout(sendContinue, 500);
+    }
+
+    self.incomingSink.setTarget(self.debugConnection);
+  }
+
+  function disconnect() {
+    if (self.debugConnection) {
+      self.debugConnection.end();
+      self.debugConnection = null;
+    }
+  }
+};
+
+DEp.stop = function stop() {
+  var proc = this.inspectorProcess;
+  if (proc && proc.kill) {
+    this.inspectorProcess = null;
+    proc.kill();
+  }
+
+  if (this.interceptServer) {
+    this.interceptServer.close();
+    this.interceptServer = null;
+  }
+
+  if (this.debugConnection) {
+    this.debugConnection.end();
+    this.debugConnection = null;
+  }
+};
+
+// A simple wrapper object for writable streams that keeps a backlog of
+// data written before the stream is available, and writes that data to the
+// stream when the stream becomes available.
+function BackloggedStreamWriter(target) {
+  assert.ok(this instanceof BackloggedStreamWriter);
+  this.backlog = [];
+  this.target = target || null;
 }
 
+var BSWp = BackloggedStreamWriter.prototype;
+
+BSWp.write = function write(buffer) {
+  if (this.target) {
+    this.target.write(buffer);
+  } else {
+    this.backlog.push(buffer);
+  }
+};
+
+BSWp.setTarget = function setTarget(target) {
+  if (this.target &&
+      this.target !== target) {
+    this.clear();
+  }
+
+  this.target = target;
+
+  if (target) {
+    var clear = this.clear.bind(this);
+    target.on("close", clear);
+    target.on("end", clear);
+
+    if (this.backlog.length > 0) {
+      _.each(this.backlog.splice(0), this.write, this);
+    }
+  }
+
+  return target;
+};
+
+BSWp.clear = function clear() {
+  this.backlog.length = 0;
+  this.target = null;
+};
+
 function banner(debugPort) {
   debugPort = +(debugPort || 5858);
-  var proc = debugPortToProcess[debugPort];
+  var entry = debugEntries[debugPort];
+  var proc = entry && entry.inspectorProcess;
   assert.strictEqual(typeof proc.url, "string");
 
   return [
@@ -66,35 +301,25 @@ function banner(debugPort) {
       "visit this URL in your web browser:"
     ].join(EOL)),
     chalk.cyan(proc.url),
-    "",
-    chalk.green([
-      "To debug the server process using the command-line node debugger, ",
-      "execute this command in another terminal window:",
-    ].join(EOL)),
-    chalk.cyan(process.execPath + " debug localhost:" + debugPort),
     EOL
   ].join(EOL);
 }
 
 function stop(debugPort) {
   debugPort = +(debugPort || 5858);
-
-  var proc = debugPortToProcess[debugPort];
-  if (proc.kill) {
-    console.error("killed " + proc.pid);
-    proc.kill();
+  var entry = debugEntries[debugPort];
+  delete debugEntries[debugPort];
+  if (entry) {
+    entry.stop();
   }
-
-  delete debugPortToProcess[debugPort];
 }
 
 require("./cleanup.js").onExit(function killAll() {
-  for (var debugPort in debugPortToProcess) {
+  for (var debugPort in debugEntries) {
     stop(debugPort);
   }
-  debugPortToProcess.length = 0;
+  debugEntries.length = 0;
 });
 
 exports.start = start;
-exports.banner = banner;
 exports.stop = stop;
diff --git a/tools/run-app.js b/tools/run-app.js
index 8de487e5df..8fdf52aca3 100644
--- a/tools/run-app.js
+++ b/tools/run-app.js
@@ -97,11 +97,9 @@ _.extend(AppProcess.prototype, {
 
     eachline(self.proc.stderr, 'utf8', fiberHelpers.inBareFiber(function (line) {
       if (self.debugPort &&
-          line.indexOf("debugger listening on port " + self.debugPort) >= 0) {
+          line.indexOf("debugger listening on port ") >= 0) {
         Console.enableProgressDisplay(false);
-        process.stdout.write(
-          require("./inspector.js").banner(self.debugPort)
-        );
+        return;
       }
 
       runLog.logAppOutput(line, true);
@@ -207,21 +205,30 @@ _.extend(AppProcess.prototype, {
     var child_process = require('child_process');
 
     var opts = _.clone(self.nodeOptions);
+    var entryPoint = path.join(self.bundlePath, 'main.js');
 
     if (self.debugPort) {
-      require("./inspector.js").start(self.debugPort);
-      opts.push("--debug-brk=" + self.debugPort);
+      var attach = require("./inspector.js").start(
+        self.debugPort,
+        entryPoint
+      );
+      opts.push("--debug-brk=" + attach.suggestedDebugBrkPort);
     }
 
     opts.push(
-      path.join(self.bundlePath, 'main.js'),
-      '--parent-pid',
+      entryPoint, '--parent-pid',
       process.env.METEOR_BAD_PARENT_PID_FOR_TEST ? "foobar" : process.pid
     );
 
-    return child_process.spawn(process.execPath, opts, {
+    var child = child_process.spawn(process.execPath, opts, {
       env: self._computeEnvironment()
     });
+
+    if (attach) {
+      attach(child);
+    }
+
+    return child;
   }
 });