diff --git a/bot.py b/bot.py
index 0b0d773..b999281 100644
--- a/bot.py
+++ b/bot.py
@@ -70,7 +70,7 @@ HELP_TEXT = """**AI Bot Commands**
 - `!ai models` — List available models
 - `!ai set-model <model>` — Set model for this room
 - `!ai search <query>` — Search documents (WildFiles)
-- `!ai connect <api-key>` — Connect your WildFiles account (DM only)
+- `!ai connect` — Connect your WildFiles account (opens browser approval)
 - `!ai disconnect` — Disconnect your WildFiles account
 - `!ai auto-rename on|off` — Auto-rename room based on conversation topic
 - **@mention the bot** or start with `!ai` for a regular AI response"""
@@ -181,6 +181,7 @@ class Bot:
         self._loaded_rooms: set[str] = set()  # rooms where we've loaded state
         self._sync_token_received = False
         self._verifications: dict[str, dict] = {}  # txn_id -> verification state
+        self._pending_connects: dict[str, str] = {}  # matrix_user_id -> device_code
 
     @staticmethod
     def _load_user_keys() -> dict[str, str]:
@@ -419,8 +420,9 @@ class Bot:
         if cmd == "help":
             await self._send_text(room.room_id, HELP_TEXT)
 
-        elif cmd.startswith("connect "):
-            await self._handle_connect(room, cmd[8:].strip(), event)
+        elif cmd == "connect" or cmd.startswith("connect "):
+            api_key = cmd[8:].strip() if cmd.startswith("connect ") else ""
+            await self._handle_connect(room, api_key, event)
 
         elif cmd == "disconnect":
             await self._handle_disconnect(room, event)
@@ -501,41 +503,69 @@ class Bot:
                 await self._send_text(room.room_id, f"Unknown command: `{cmd}`\n\n{HELP_TEXT}")
 
     async def _handle_connect(self, room, api_key: str, event=None):
-        """Handle !ai connect <api-key> — validate and store user's WildFiles API key."""
+        """Handle !ai connect — SSO device flow, or !ai connect <key> as fallback."""
         sender = event.sender if event else None
-        if not api_key:
-            await self._send_text(room.room_id, "Usage: `!ai connect <wildfiles-api-key>`")
-            return
-
-        # Redact the message containing the API key for security
-        if event:
-            try:
-                await self.client.room_redact(room.room_id, event.event_id, reason="API key redacted for security")
-            except Exception:
-                logger.debug("Could not redact connect message", exc_info=True)
 
         if not self.rag.base_url:
             await self._send_text(room.room_id, "WildFiles is not configured.")
             return
 
-        # Validate the key
-        stats = await self.rag.validate_key(api_key)
-        if stats is None:
-            await self._send_text(room.room_id, "Invalid API key. Please check and try again.")
+        # Fallback: direct API key provided
+        if api_key:
+            # Redact the message containing the API key for security
+            if event:
+                try:
+                    await self.client.room_redact(room.room_id, event.event_id, reason="API key redacted for security")
+                except Exception:
+                    logger.debug("Could not redact connect message", exc_info=True)
+
+            stats = await self.rag.validate_key(api_key)
+            if stats is None:
+                await self._send_text(room.room_id, "Invalid API key. Please check and try again.")
+                return
+
+            self.user_keys[sender] = api_key
+            self._save_user_keys()
+            org_name = stats.get("organization", "unknown")
+            total = stats.get("total_documents", 0)
+            await self._send_text(
+                room.room_id,
+                f"Connected to WildFiles (org: **{org_name}**, {total} documents). "
+                f"Your documents are now searchable.",
+            )
+            logger.info("User %s connected WildFiles key (org: %s)", sender, org_name)
             return
 
-        # Store the key
-        self.user_keys[sender] = api_key
-        self._save_user_keys()
+        # SSO device authorization flow
+        if sender and sender in self._pending_connects:
+            await self._send_text(room.room_id, "A connect flow is already in progress. Please complete or wait for it to expire.")
+            return
+
+        try:
+            async with httpx.AsyncClient(timeout=10.0) as client:
+                resp = await client.post(f"{self.rag.base_url}/api/v1/auth/device/code")
+                resp.raise_for_status()
+                data = resp.json()
+        except Exception:
+            logger.exception("Failed to start device auth flow")
+            await self._send_text(room.room_id, "Failed to start connection flow. Please try again later.")
+            return
+
+        device_code = data["device_code"]
+        user_code = data["user_code"]
+        verification_url = data["verification_url"]
 
-        org_name = stats.get("organization", "unknown")
-        total = stats.get("total_documents", 0)
         await self._send_text(
             room.room_id,
-            f"Connected to WildFiles (org: **{org_name}**, {total} documents). "
-            f"Your documents are now searchable.",
+            f"To connect WildFiles, visit:\n\n"
+            f"**{verification_url}**\n\n"
+            f"and enter code: **{user_code}**\n\n"
+            f"_This link expires in 10 minutes._",
         )
-        logger.info("User %s connected WildFiles key (org: %s)", sender, org_name)
+
+        # Track pending connect and start polling
+        self._pending_connects[sender] = device_code
+        asyncio.create_task(self._poll_device_auth(room.room_id, sender, device_code))
 
     async def _handle_disconnect(self, room, event=None):
         """Handle !ai disconnect — remove stored WildFiles API key."""
@@ -548,6 +578,46 @@ class Bot:
         else:
             await self._send_text(room.room_id, "No WildFiles account connected.")
 
+    async def _poll_device_auth(self, room_id: str, sender: str, device_code: str):
+        """Poll WildFiles for device auth approval (5s interval, 10 min max)."""
+        poll_url = f"{self.rag.base_url}/api/v1/auth/device/status"
+        try:
+            for _ in range(120):  # 120 * 5s = 10 min
+                await asyncio.sleep(5)
+                try:
+                    async with httpx.AsyncClient(timeout=10.0) as client:
+                        resp = await client.get(poll_url, params={"device_code": device_code})
+                        resp.raise_for_status()
+                        data = resp.json()
+                except Exception:
+                    logger.debug("Device auth poll failed, retrying", exc_info=True)
+                    continue
+
+                if data["status"] == "approved":
+                    api_key = data["api_key"]
+                    org_slug = data.get("organization", "unknown")
+                    self.user_keys[sender] = api_key
+                    self._save_user_keys()
+                    await self._send_text(
+                        room_id,
+                        f"Connected to WildFiles (org: **{org_slug}**). Your documents are now searchable.",
+                    )
+                    logger.info("User %s connected via device auth (org: %s)", sender, org_slug)
+                    return
+                elif data["status"] == "expired":
+                    await self._send_text(room_id, "Connection flow expired. Type `!ai connect` to try again.")
+                    return
+
+            # Timeout after 10 minutes
+            await self._send_text(room_id, "Connection flow timed out. Type `!ai connect` to try again.")
+        except asyncio.CancelledError:
+            pass
+        except Exception:
+            logger.exception("Device auth polling error")
+            await self._send_text(room_id, "Connection flow failed. Type `!ai connect` to try again.")
+        finally:
+            self._pending_connects.pop(sender, None)
+
     async def _respond_with_ai(self, room, user_message: str, sender: str = None):
         model = self.room_models.get(room.room_id, DEFAULT_MODEL)