diff --git a/background.js b/background.js
index 6720f3e..960635e 100644
--- a/background.js
+++ b/background.js
@@ -20,6 +20,46 @@ const DEFAULT_SETTINGS = {
   theme: "system"
 };
 
+const OUTPUT_STORAGE_KEY = "lastOutput";
+const AUTO_RUN_KEY = "autoRunDefaultTask";
+let activeAbortController = null;
+let keepalivePort = null;
+const streamState = {
+  active: false,
+  outputText: "",
+  subscribers: new Set()
+};
+
+function resetAbort() {
+  if (activeAbortController) {
+    activeAbortController.abort();
+    activeAbortController = null;
+  }
+  closeKeepalive();
+}
+
+function openKeepalive(tabId) {
+  if (!tabId || keepalivePort) return;
+  try {
+    keepalivePort = chrome.tabs.connect(tabId, { name: "wwcompanion-keepalive" });
+    keepalivePort.onDisconnect.addListener(() => {
+      keepalivePort = null;
+    });
+  } catch {
+    keepalivePort = null;
+  }
+}
+
+function closeKeepalive() {
+  if (!keepalivePort) return;
+  try {
+    keepalivePort.disconnect();
+  } catch {
+    // Ignore disconnect failures.
+  }
+  keepalivePort = null;
+}
+
 chrome.runtime.onInstalled.addListener(async () => {
   const stored = await chrome.storage.local.get(Object.keys(DEFAULT_SETTINGS));
   const updates = {};
@@ -42,29 +82,42 @@ chrome.runtime.onInstalled.addListener(async () => {
 chrome.runtime.onConnect.addListener((port) => {
   if (port.name !== "analysis") return;
 
-  let abortController = null;
+  streamState.subscribers.add(port);
+  port.onDisconnect.addListener(() => {
+    streamState.subscribers.delete(port);
+  });
 
-  const resetAbort = () => {
-    if (abortController) abortController.abort();
-    abortController = null;
-  };
+  if (streamState.active) {
+    safePost(port, {
+      type: "SYNC",
+      text: streamState.outputText,
+      streaming: true
+    });
+  }
 
   port.onMessage.addListener((message) => {
     if (message?.type === "START_ANALYSIS") {
+      streamState.outputText = "";
       resetAbort();
-      abortController = new AbortController();
-      void handleAnalysisRequest(port, message.payload, abortController.signal).catch(
-        (error) => {
+      const controller = new AbortController();
+      activeAbortController = controller;
+      const request = handleAnalysisRequest(port, message.payload, controller.signal);
+      void request
+        .catch((error) => {
           if (error?.name === "AbortError") {
-            port.postMessage({ type: "ABORTED" });
+            safePost(port, { type: "ABORTED" });
             return;
           }
-          port.postMessage({
+          safePost(port, {
             type: "ERROR",
             message: error?.message || "Unknown error during analysis."
           });
-        }
-      );
+        })
+        .finally(() => {
+          if (activeAbortController === controller) {
+            activeAbortController = null;
+          }
+        });
       return;
     }
 
@@ -73,9 +126,14 @@ chrome.runtime.onConnect.addListener((port) => {
     }
   });
 
-  port.onDisconnect.addListener(() => {
-    resetAbort();
-  });
+});
+
+chrome.runtime.onMessage.addListener((message) => {
+  if (message?.type !== "RUN_DEFAULT_TASK") return;
+  void chrome.storage.local.set({ [AUTO_RUN_KEY]: Date.now() });
+  if (chrome.action?.openPopup) {
+    void chrome.action.openPopup().catch(() => {});
+  }
 });
 
 function buildUserMessage(resume, task, posting) {
@@ -91,7 +149,24 @@ function buildUserMessage(resume, task, posting) {
   ].join("\n");
 }
 
+function safePost(port, message) {
+  try {
+    port.postMessage(message);
+  } catch {
+    // Port can disconnect when the popup closes; ignore post failures.
+  }
+}
+
+function broadcast(message) {
+  for (const port of streamState.subscribers) {
+    safePost(port, message);
+  }
+}
+
 async function handleAnalysisRequest(port, payload, signal) {
+  streamState.outputText = "";
+  streamState.active = true;
+
   const {
     apiKey,
     apiBaseUrl,
@@ -101,49 +176,62 @@ async function handleAnalysisRequest(port, payload, signal) {
     systemPrompt,
     resume,
     taskText,
-    postingText
+    postingText,
+    tabId
   } = payload || {};
 
   if (!apiBaseUrl) {
-    port.postMessage({ type: "ERROR", message: "Missing API base URL." });
+    safePost(port, { type: "ERROR", message: "Missing API base URL." });
     return;
   }
 
   if (apiKeyHeader && !apiKey) {
-    port.postMessage({ type: "ERROR", message: "Missing API key." });
+    safePost(port, { type: "ERROR", message: "Missing API key." });
     return;
   }
 
   if (!model) {
-    port.postMessage({ type: "ERROR", message: "Missing model name." });
+    safePost(port, { type: "ERROR", message: "Missing model name." });
     return;
   }
 
   if (!postingText) {
-    port.postMessage({ type: "ERROR", message: "No job posting text provided." });
+    safePost(port, { type: "ERROR", message: "No job posting text provided." });
     return;
   }
 
   if (!taskText) {
-    port.postMessage({ type: "ERROR", message: "No task prompt selected." });
+    safePost(port, { type: "ERROR", message: "No task prompt selected." });
     return;
   }
 
   const userMessage = buildUserMessage(resume, taskText, postingText);
 
-  await streamChatCompletion({
-    apiKey,
-    apiBaseUrl,
-    apiKeyHeader,
-    apiKeyPrefix,
-    model,
-    systemPrompt: systemPrompt || "",
-    userMessage,
-    signal,
-    onDelta: (text) => port.postMessage({ type: "DELTA", text })
-  });
+  await chrome.storage.local.set({ [OUTPUT_STORAGE_KEY]: "" });
+  openKeepalive(tabId);
 
-  port.postMessage({ type: "DONE" });
+  try {
+    await streamChatCompletion({
+      apiKey,
+      apiBaseUrl,
+      apiKeyHeader,
+      apiKeyPrefix,
+      model,
+      systemPrompt: systemPrompt || "",
+      userMessage,
+      signal,
+      onDelta: (text) => {
+        streamState.outputText += text;
+        broadcast({ type: "DELTA", text });
+      }
+    });
+
+    broadcast({ type: "DONE" });
+  } finally {
+    streamState.active = false;
+    await chrome.storage.local.set({ [OUTPUT_STORAGE_KEY]: streamState.outputText });
+    closeKeepalive();
+  }
 }
 
 function buildChatUrl(apiBaseUrl) {
diff --git a/content.js b/content.js
index e3dcbdc..0a4d308 100644
--- a/content.js
+++ b/content.js
@@ -8,6 +8,14 @@ const HEADER_LINES = new Set([
   "SERVICE TEAM"
 ]);
 
+const ACTION_BAR_SELECTOR = "nav.floating--action-bar";
+const INJECTED_ATTR = "data-wwcompanion-default-task";
+const DEFAULT_TASK_LABEL = "Default WWCompanion Task";
+
+function isJobPostingOpen() {
+  return document.getElementsByClassName("modal__content").length > 0;
+}
+
 function sanitizePostingText(text) {
   let cleaned = text.replaceAll("fiber_manual_record", "");
   const lines = cleaned.split(/\r?\n/);
@@ -23,6 +31,78 @@ function sanitizePostingText(text) {
   return cleaned.trim();
 }
 
+function buildDefaultTaskButton(templateButton) {
+  const button = document.createElement("button");
+  button.type = "button";
+  button.textContent = DEFAULT_TASK_LABEL;
+  button.className = templateButton.className;
+  button.setAttribute(INJECTED_ATTR, "true");
+  button.setAttribute("aria-label", DEFAULT_TASK_LABEL);
+  button.addEventListener("click", () => {
+    document.dispatchEvent(new CustomEvent("WWCOMPANION_RUN_DEFAULT_TASK"));
+    chrome.runtime.sendMessage({ type: "RUN_DEFAULT_TASK" });
+  });
+  return button;
+}
+
+function getActionBars() {
+  return [...document.querySelectorAll(ACTION_BAR_SELECTOR)];
+}
+
+function getActionBarButtonCount(bar) {
+  return bar.querySelectorAll(`button:not([${INJECTED_ATTR}])`).length;
+}
+
+function selectTargetActionBar(bars) {
+  if (!bars.length) return null;
+  let best = bars[0];
+  let bestCount = getActionBarButtonCount(best);
+  for (const bar of bars.slice(1)) {
+    const count = getActionBarButtonCount(bar);
+    if (count > bestCount) {
+      best = bar;
+      bestCount = count;
+    }
+  }
+  return best;
+}
+
+function ensureDefaultTaskButton() {
+  const bars = getActionBars();
+  if (!bars.length) return;
+
+  if (!isJobPostingOpen()) {
+    for (const bar of bars) {
+      const injected = bar.querySelector(`[${INJECTED_ATTR}]`);
+      if (injected) injected.remove();
+    }
+    return;
+  }
+
+  const toolbar = selectTargetActionBar(bars);
+  if (!toolbar) return;
+
+  for (const bar of bars) {
+    if (bar === toolbar) continue;
+    const injected = bar.querySelector(`[${INJECTED_ATTR}]`);
+    if (injected) injected.remove();
+  }
+
+  const existing = toolbar.querySelector(`[${INJECTED_ATTR}]`);
+  if (existing) return;
+
+  const templateButton = toolbar.querySelector("button");
+  if (!templateButton) return;
+
+  const button = buildDefaultTaskButton(templateButton);
+  const firstChild = toolbar.firstElementChild;
+  if (firstChild) {
+    toolbar.insertBefore(button, firstChild);
+  } else {
+    toolbar.appendChild(button);
+  }
+}
+
 function extractPostingText() {
   const contents = [...document.getElementsByClassName("modal__content")];
   if (!contents.length) {
@@ -46,3 +126,15 @@ chrome.runtime.onMessage.addListener((message, _sender, sendResponse) => {
   const result = extractPostingText();
   sendResponse(result);
 });
+
+chrome.runtime.onConnect.addListener((port) => {
+  if (port.name !== "wwcompanion-keepalive") return;
+  port.onDisconnect.addListener(() => {});
+});
+
+const observer = new MutationObserver(() => {
+  ensureDefaultTaskButton();
+});
+
+observer.observe(document.documentElement, { childList: true, subtree: true });
+ensureDefaultTaskButton();
diff --git a/manifest.json b/manifest.json
index 2084734..5466dfd 100644
--- a/manifest.json
+++ b/manifest.json
@@ -1,8 +1,8 @@
 {
   "manifest_version": 3,
   "name": "WWCompanion",
-  "version": "0.1.4",
-  "description": "Manual reasoning companion for WaterlooWorks job postings.",
+  "version": "0.2.1",
+  "description": "AI companion for WaterlooWorks job postings.",
   "permissions": ["storage", "activeTab"],
   "host_permissions": ["https://waterlooworks.uwaterloo.ca/*"],
   "action": {
diff --git a/popup.js b/popup.js
index 70b4d18..293a044 100644
--- a/popup.js
+++ b/popup.js
@@ -15,14 +15,15 @@ const copyRawBtn = document.getElementById("copyRawBtn");
 const clearOutputBtn = document.getElementById("clearOutputBtn");
 
 const OUTPUT_STORAGE_KEY = "lastOutput";
-let persistTimer = null;
+const AUTO_RUN_KEY = "autoRunDefaultTask";
 
 const state = {
   postingText: "",
   tasks: [],
   port: null,
   isAnalyzing: false,
-  outputRaw: ""
+  outputRaw: "",
+  autoRunPending: false
 };
 
 function getStorage(keys) {
@@ -230,20 +231,9 @@ function renderOutput() {
 }
 
 function persistOutputNow() {
-  if (persistTimer) {
-    clearTimeout(persistTimer);
-    persistTimer = null;
-  }
   return chrome.storage.local.set({ [OUTPUT_STORAGE_KEY]: state.outputRaw });
 }
 
-function schedulePersistOutput() {
-  if (persistTimer) clearTimeout(persistTimer);
-  persistTimer = setTimeout(() => {
-    void persistOutputNow();
-  }, 250);
-}
-
 function setStatus(message) {
   statusEl.textContent = message;
 }
@@ -263,6 +253,7 @@ function setAnalyzing(isAnalyzing) {
     buttonRow.classList.toggle("hidden", isAnalyzing);
     stopRow.classList.toggle("hidden", !isAnalyzing);
   }
+  updateTaskSelectState();
 }
 
 function updatePostingCount() {
@@ -282,17 +273,30 @@ function renderTasks(tasks) {
     option.textContent = "No tasks configured";
     option.value = "";
     taskSelect.appendChild(option);
-    taskSelect.disabled = true;
+    updateTaskSelectState();
     return;
   }
 
-  taskSelect.disabled = false;
   for (const task of tasks) {
     const option = document.createElement("option");
     option.value = task.id;
     option.textContent = task.name || "Untitled task";
     taskSelect.appendChild(option);
   }
+  updateTaskSelectState();
+}
+
+function updateTaskSelectState() {
+  const hasTasks = state.tasks.length > 0;
+  taskSelect.disabled = state.isAnalyzing || !hasTasks;
+}
+
+function isWaterlooWorksUrl(url) {
+  try {
+    return new URL(url).hostname === "waterlooworks.uwaterloo.ca";
+  } catch {
+    return false;
+  }
 }
 
 function sendToActiveTab(message) {
@@ -304,6 +308,11 @@ function sendToActiveTab(message) {
         return;
       }
 
+      if (!isWaterlooWorksUrl(tab.url || "")) {
+        reject(new Error("Open waterlooworks.uwaterloo.ca to use this."));
+        return;
+      }
+
       chrome.tabs.sendMessage(tab.id, message, (response) => {
         const error = chrome.runtime.lastError;
         if (error) {
@@ -328,28 +337,34 @@ function ensurePort() {
     if (message?.type === "DELTA") {
       state.outputRaw += message.text;
       renderOutput();
-      schedulePersistOutput();
+      return;
+    }
+
+    if (message?.type === "SYNC") {
+      state.outputRaw = message.text || "";
+      renderOutput();
+      if (message.streaming) {
+        setAnalyzing(true);
+        setStatus("Analyzing...");
+      }
       return;
     }
 
     if (message?.type === "DONE") {
       setAnalyzing(false);
       setStatus("Done");
-      void persistOutputNow();
       return;
     }
 
     if (message?.type === "ABORTED") {
       setAnalyzing(false);
       setStatus("Aborted.");
-      void persistOutputNow();
       return;
     }
 
     if (message?.type === "ERROR") {
       setAnalyzing(false);
       setStatus(message.message || "Error during analysis.");
-      void persistOutputNow();
     }
   });
 
@@ -365,6 +380,7 @@ function ensurePort() {
 async function loadTasks() {
   const { tasks = [] } = await getStorage(["tasks"]);
   renderTasks(tasks);
+  maybeRunDefaultTask();
 }
 
 async function loadTheme() {
@@ -398,6 +414,13 @@ async function handleAnalyze() {
     return;
   }
 
+  const tabs = await chrome.tabs.query({ active: true, currentWindow: true });
+  const tab = tabs[0];
+  if (!tab?.url || !isWaterlooWorksUrl(tab.url)) {
+    setStatus("Open waterlooworks.uwaterloo.ca to run tasks.");
+    return;
+  }
+
   const taskId = taskSelect.value;
   const task = state.tasks.find((item) => item.id === taskId);
   if (!task) {
@@ -436,7 +459,6 @@ async function handleAnalyze() {
 
   state.outputRaw = "";
   renderOutput();
-  void persistOutputNow();
   setAnalyzing(true);
   setStatus("Analyzing...");
 
@@ -452,7 +474,8 @@ async function handleAnalyze() {
       systemPrompt: systemPrompt || "",
       resume: resume || "",
       taskText: task.text || "",
-      postingText: state.postingText
+      postingText: state.postingText,
+      tabId: tab.id
     }
   });
 }
@@ -526,9 +549,42 @@ async function loadSavedOutput() {
   renderOutput();
 }
 
+async function loadAutoRunRequest() {
+  const stored = await getStorage([AUTO_RUN_KEY]);
+  if (stored[AUTO_RUN_KEY]) {
+    state.autoRunPending = true;
+    await chrome.storage.local.remove(AUTO_RUN_KEY);
+  }
+  maybeRunDefaultTask();
+}
+
+function maybeRunDefaultTask() {
+  if (!state.autoRunPending) return;
+  if (state.isAnalyzing) return;
+  if (!state.tasks.length) return;
+  taskSelect.value = state.tasks[0].id;
+  state.autoRunPending = false;
+  void handleExtractAndAnalyze();
+}
+
 loadSavedOutput();
+loadAutoRunRequest();
+ensurePort();
 
 chrome.storage.onChanged.addListener((changes) => {
+  if (changes[AUTO_RUN_KEY]?.newValue) {
+    state.autoRunPending = true;
+    void chrome.storage.local.remove(AUTO_RUN_KEY);
+    maybeRunDefaultTask();
+  }
+
+  if (changes[OUTPUT_STORAGE_KEY]?.newValue !== undefined) {
+    if (!state.isAnalyzing || !state.port) {
+      state.outputRaw = changes[OUTPUT_STORAGE_KEY].newValue || "";
+      renderOutput();
+    }
+  }
+
   if (changes.theme) {
     applyTheme(changes.theme.newValue || "system");
   }