diff --git a/frontend/src/pages/DataSourcesPage.tsx b/frontend/src/pages/DataSourcesPage.tsx
index 5f61176d..b09d9d41 100644
--- a/frontend/src/pages/DataSourcesPage.tsx
+++ b/frontend/src/pages/DataSourcesPage.tsx
@@ -81,7 +81,7 @@ function InlineConnectForm({
           borderRadius: 6, fontSize: 12, cursor: 'pointer',
         }}
       >
-        {loading ? 'Connecting...' : 'Connect'}
+        Connect
       </button>
     </div>
   );
@@ -327,20 +327,54 @@ function DataSourcesSection() {
     }
   }, [connectors, loadSyncStatuses]);
 
+  const [connectingId, setConnectingId] = useState<string | null>(null);
+  const [connectStage, setConnectStage] = useState<string>('');
+  const [connectError, setConnectError] = useState<string>('');
+
   const handleConnect = async (id: string, req: ConnectRequest) => {
     setLoading(true);
+    setConnectingId(id);
+    setConnectStage('Connecting...');
+    setConnectError('');
     try {
       await connectSource(id, req);
-      setExpandedId(null);
-      for (let i = 0; i < 30; i++) {
-        await new Promise((r) => setTimeout(r, 3000));
-        await loadConnectors();
+      setConnectStage('Connected! Starting sync...');
+
+      // Wait for connector to show as connected
+      for (let i = 0; i < 20; i++) {
+        await new Promise((r) => setTimeout(r, 2000));
         const updated = await listConnectors();
         const target = updated.find((c) => c.connector_id === id);
-        if (target?.connected) break;
+        if (target?.connected) {
+          setConnectors(updated.map((c) => ({
+            connector_id: c.connector_id,
+            display_name: c.display_name,
+            connected: c.connected,
+            chunks: (c as any).chunks || 0,
+          })));
+          break;
+        }
+        setConnectStage(i < 5 ? 'Authenticating...' : 'Waiting for connection...');
       }
-    } catch { /* */ } finally {
+
+      // Trigger sync
+      setConnectStage('Syncing data...');
+      try {
+        await triggerSync(id);
+      } catch { /* sync may already be running */ }
+
+      // Close form after a brief moment
+      await new Promise((r) => setTimeout(r, 1500));
+      setExpandedId(null);
+      loadConnectors();
+      loadSyncStatuses();
+    } catch (err: any) {
+      setConnectError(err.message || 'Connection failed');
+      setConnectStage('');
+    } finally {
       setLoading(false);
+      setConnectingId(null);
+      setConnectStage('');
     }
   };
 
@@ -524,10 +558,43 @@ function DataSourcesSection() {
                     {meta?.inputFields && (
                       <InlineConnectForm
                         fields={meta.inputFields}
-                        loading={loading}
+                        loading={loading && connectingId === c.connector_id}
                         onSubmit={(req) => handleConnect(c.connector_id, req)}
                       />
                     )}
+                    {/* Connection progress */}
+                    {connectingId === c.connector_id && connectStage && (
+                      <div style={{ marginTop: 8 }}>
+                        <div style={{
+                          display: 'flex', alignItems: 'center', gap: 6,
+                          fontSize: 12, color: '#f59e0b',
+                        }}>
+                          <div className="animate-spin" style={{
+                            width: 12, height: 12, borderRadius: '50%',
+                            border: '2px solid #f59e0b',
+                            borderTopColor: 'transparent',
+                          }} />
+                          {connectStage}
+                        </div>
+                        <div style={{
+                          height: 3, borderRadius: 2, marginTop: 6,
+                          background: 'var(--color-bg-tertiary)',
+                          overflow: 'hidden',
+                        }}>
+                          <div style={{
+                            height: '100%', borderRadius: 2, background: '#f59e0b',
+                            width: connectStage.includes('Sync') ? '75%' : connectStage.includes('Connected') ? '50%' : '25%',
+                            transition: 'width 0.5s ease',
+                          }} />
+                        </div>
+                      </div>
+                    )}
+                    {/* Connection error */}
+                    {connectError && connectingId === null && expandedId === c.connector_id && (
+                      <div style={{ fontSize: 11, color: '#ef4444', marginTop: 6 }}>
+                        {connectError}
+                      </div>
+                    )}
                   </div>
                 )}
               </div>
diff --git a/src/openjarvis/connectors/gcalendar.py b/src/openjarvis/connectors/gcalendar.py
index 5b7a85c3..bc730d96 100644
--- a/src/openjarvis/connectors/gcalendar.py
+++ b/src/openjarvis/connectors/gcalendar.py
@@ -316,9 +316,12 @@ class GCalendarConnector(BaseConnector):
             page_token: Optional[str] = cursor
 
             while True:
-                events_resp = _gcal_api_events_list(
-                    token, calendar_id, page_token=page_token
-                )
+                try:
+                    events_resp = _gcal_api_events_list(
+                        token, calendar_id, page_token=page_token
+                    )
+                except httpx.HTTPStatusError:
+                    break
                 events: List[Dict[str, Any]] = events_resp.get("items", [])
 
                 for event in events:
diff --git a/src/openjarvis/connectors/obsidian.py b/src/openjarvis/connectors/obsidian.py
index 1625d146..db8e6a9e 100644
--- a/src/openjarvis/connectors/obsidian.py
+++ b/src/openjarvis/connectors/obsidian.py
@@ -8,7 +8,7 @@ can be ingested by the knowledge pipeline.
 from __future__ import annotations
 
 import os
-from datetime import datetime
+from datetime import datetime, timezone
 from pathlib import Path
 from typing import Any, Dict, Iterator, List, Optional, Tuple
 from urllib.parse import quote
@@ -161,7 +161,7 @@ class ObsidianConnector(BaseConnector):
 
         for fpath in collected_paths:
             # Apply since filter based on mtime
-            mtime = datetime.fromtimestamp(fpath.stat().st_mtime)
+            mtime = datetime.fromtimestamp(fpath.stat().st_mtime, tz=timezone.utc)
             if since is not None and mtime < since:
                 continue
 
diff --git a/src/openjarvis/server/agent_manager_routes.py b/src/openjarvis/server/agent_manager_routes.py
index ae4b1e73..ef41b765 100644
--- a/src/openjarvis/server/agent_manager_routes.py
+++ b/src/openjarvis/server/agent_manager_routes.py
@@ -719,7 +719,7 @@ async def _stream_managed_agent(
                 # Stream progress events and final content
                 while True:
                     try:
-                        event = await asyncio.to_thread(progress_q.get, timeout=120)
+                        event = await asyncio.to_thread(progress_q.get, timeout=600)
                     except Exception:
                         # Timeout
                         yield _sse_chunk(chunk_id, model, "Agent timed out.")