diff --git a/extension/src/background.ts b/extension/src/background.ts
index 4d9de55..b170555 100644
--- a/extension/src/background.ts
+++ b/extension/src/background.ts
@@ -9,6 +9,7 @@ let ws: WebSocket | null = null
 let childSessions: Map<string, number> = new Map()
 let nextSessionId = 1
 let playwriterGroupId: number | null = null
+let syncTabGroupQueue: Promise<void> = Promise.resolve()
 
 const store = createStore<ExtensionState>(() => ({
   tabs: new Map(),
@@ -95,43 +96,72 @@ function sendMessage(message: any): void {
   }
 }
 
-async function addTabToGroup(tabId: number): Promise<void> {
+async function syncTabGroup(): Promise<void> {
   try {
-    if (playwriterGroupId !== null) {
-      const existingGroups = await chrome.tabGroups.query({ title: 'playwriter' })
-      if (!existingGroups.some((g) => g.id === playwriterGroupId)) {
-        playwriterGroupId = null
+    const connectedTabIds = Array.from(store.getState().tabs.entries())
+      .filter(([_, info]) => info.state === 'connected')
+      .map(([tabId]) => tabId)
+
+    const existingGroups = await chrome.tabGroups.query({ title: 'playwriter' })
+
+    if (existingGroups.length > 1) {
+      const [keep, ...duplicates] = existingGroups
+      for (const group of duplicates) {
+        const tabsInDupe = await chrome.tabs.query({ groupId: group.id })
+        for (const tab of tabsInDupe) {
+          if (tab.id) {
+            await chrome.tabs.ungroup(tab.id)
+          }
+        }
+        logger.debug('Removed duplicate playwriter group:', group.id)
+      }
+      playwriterGroupId = keep.id
+    } else if (existingGroups.length === 1) {
+      playwriterGroupId = existingGroups[0].id
+    }
+
+    if (connectedTabIds.length === 0) {
+      for (const group of existingGroups) {
+        const tabsInGroup = await chrome.tabs.query({ groupId: group.id })
+        for (const tab of tabsInGroup) {
+          if (tab.id) {
+            await chrome.tabs.ungroup(tab.id)
+          }
+        }
+        logger.debug('Cleared playwriter group:', group.id)
+      }
+      playwriterGroupId = null
+      return
+    }
+
+    const allTabs = await chrome.tabs.query({})
+    const tabsInGroup = allTabs.filter((t) => t.groupId === playwriterGroupId && t.id !== undefined)
+    const tabIdsInGroup = new Set(tabsInGroup.map((t) => t.id!))
+
+    const tabsToAdd = connectedTabIds.filter((id) => !tabIdsInGroup.has(id))
+    const tabsToRemove = Array.from(tabIdsInGroup).filter((id) => !connectedTabIds.includes(id))
+
+    for (const tabId of tabsToRemove) {
+      try {
+        await chrome.tabs.ungroup(tabId)
+        logger.debug('Removed tab from group:', tabId)
+      } catch (e: any) {
+        logger.debug('Failed to ungroup tab:', tabId, e.message)
       }
     }
 
-    if (playwriterGroupId === null) {
-      playwriterGroupId = await chrome.tabs.group({ tabIds: [tabId] })
-      await chrome.tabGroups.update(playwriterGroupId, { title: 'playwriter', color: 'green' })
-      logger.debug('Created tab group:', playwriterGroupId)
-    } else {
-      await chrome.tabs.group({ tabIds: [tabId], groupId: playwriterGroupId })
-      logger.debug('Added tab to existing group:', tabId)
-    }
-  } catch (error: any) {
-    logger.debug('Failed to add tab to group:', error.message)
-  }
-}
-
-async function removeTabFromGroup(tabId: number): Promise<void> {
-  try {
-    await chrome.tabs.ungroup(tabId)
-    logger.debug('Removed tab from group:', tabId)
-
-    if (playwriterGroupId !== null) {
-      const groups = await chrome.tabGroups.query({ title: 'playwriter' })
-      const group = groups.find((g) => g.id === playwriterGroupId)
-      if (!group) {
-        playwriterGroupId = null
-        logger.debug('Tab group was deleted')
+    if (tabsToAdd.length > 0) {
+      if (playwriterGroupId === null) {
+        playwriterGroupId = await chrome.tabs.group({ tabIds: tabsToAdd })
+        await chrome.tabGroups.update(playwriterGroupId, { title: 'playwriter', color: 'green' })
+        logger.debug('Created tab group:', playwriterGroupId, 'with tabs:', tabsToAdd)
+      } else {
+        await chrome.tabs.group({ tabIds: tabsToAdd, groupId: playwriterGroupId })
+        logger.debug('Added tabs to existing group:', tabsToAdd)
       }
     }
   } catch (error: any) {
-    logger.debug('Failed to remove tab from group:', error.message)
+    logger.debug('Failed to sync tab group:', error.message)
   }
 }
 
@@ -340,7 +370,6 @@ async function attachTab(tabId: number): Promise<Protocol.Target.TargetInfo> {
   })
 
   logger.debug('Tab attached successfully:', tabId, 'sessionId:', sessionId, 'targetId:', targetInfo.targetId)
-  await addTabToGroup(tabId)
   return targetInfo
 }
 
@@ -353,8 +382,6 @@ function detachTab(tabId: number, shouldDetachDebugger: boolean): void {
 
   logger.debug('Detaching tab:', tabId, 'sessionId:', tab.sessionId, 'shouldDetach:', shouldDetachDebugger)
 
-  void removeTabFromGroup(tabId)
-
   sendMessage({
     method: 'forwardCDPEvent',
     params: {
@@ -397,7 +424,6 @@ function closeConnection(reason: string): void {
 
   store.setState({ tabs: new Map(), connectionState: 'disconnected', errorText: undefined })
   childSessions.clear()
-  playwriterGroupId = null
 
   if (ws) {
     ws.close(1000, reason)
@@ -420,7 +446,6 @@ function handleConnectionClose(reason: string, code: number): void {
   }
 
   childSessions.clear()
-  playwriterGroupId = null
   ws = null
 
   if (reason === 'Extension Replaced' || code === 4001) {
@@ -851,9 +876,19 @@ chrome.runtime.onInstalled.addListener((details) => {
   }
 })
 
-store.subscribe(async () => {
-  logger.log(store.getState())
-  await updateIcons()
+function serializeTabs(tabs: Map<number, TabInfo>): string {
+  return JSON.stringify(Array.from(tabs.entries()))
+}
+
+store.subscribe((state, prevState) => {
+  logger.log(state)
+  void updateIcons()
+  const tabsChanged = serializeTabs(state.tabs) !== serializeTabs(prevState.tabs)
+  if (tabsChanged) {
+    syncTabGroupQueue = syncTabGroupQueue.then(syncTabGroup).catch((e) => {
+      logger.debug('syncTabGroup error:', e)
+    })
+  }
 })
 
 logger.debug(`Using relay URL: ${RELAY_URL}`)