Outlook Stuck on “Trying to Connect”? Here’s the Complete 2025 Fix
Is your Outlook stuck on “Trying to Connect” and not sending or receiving emails? This issue can appear suddenly and disrupt your entire workday.
Many Microsoft 365 users in 2025 are facing Outlook connection problems due to updates, network changes, or profile corruption. In this guide, you’ll learn why Outlook gets stuck trying to connect and how to fix it step by step.
Common Symptoms of Outlook Connection Problems
- Status bar shows “Trying to Connect” or “Disconnected”
- Emails not sending or receiving
- Calendar not updating
- Outlook freezes when opening
- Works on Outlook Web but not on desktop
Why Outlook Gets Stuck on “Trying to Connect”
- Network or DNS issues
- Corrupted Outlook profile
- Authentication token errors
- Outdated Outlook or Windows version
- Firewall, VPN, or antivirus interference
- Microsoft 365 service glitches
Fix 1 – Check Microsoft 365 Service Status
Before troubleshooting locally, check if Microsoft services are down.
- Visit Microsoft 365 Service Health (if you have admin access)
- Check Outlook Web — if web works, the issue is local
Fix 2 – Restart Outlook and Your Computer
Simple restarts often resolve temporary connection glitches.
- Close Outlook completely
- Restart your computer
- Open Outlook and check the status bar
Fix 3 – Disable Work Offline Mode
- Open Outlook
- Go to Send/Receive tab
- Ensure Work Offline is not enabled
Fix 4 – Check Network, VPN, and Firewall
VPNs and security software commonly block Outlook connections.
- Disconnect VPN temporarily
- Disable antivirus email scanning (test only)
- Ensure firewall allows Outlook
If Outlook connects after disabling one of these, that component is causing the issue.
Fix 5 – Repair Outlook Data File (OST)
- Close Outlook
- Press Windows + R and type
%localappdata%\Microsoft\Outlook - Rename your OST file
- Restart Outlook
Outlook will rebuild the OST file and reconnect to the server.
Fix 6 – Create a New Outlook Profile
A corrupted profile often causes persistent connection issues.
- Open Control Panel → Mail
- Click Show Profiles
- Add a new profile
- Set it as default
Fix 7 – Update Outlook & Windows
Connection bugs are frequently fixed via updates.
- Update Outlook from File → Office Account
- Install Windows updates
- Restart your PC
Why Outlook Connection Issues Should Be Fixed Quickly
- Emails may not send or receive
- Calendar and contacts may stop syncing
- Business communication can fail
- Deadlines and meetings may be missed
Need Help Fixing Outlook Connection Issues?
If Outlook remains stuck on “Trying to Connect,” the issue may involve:
- Account-level authentication errors
- Hidden mailbox sync problems
- Network or security policy conflicts
In such cases, getting help from a Microsoft 365 expert can restore Outlook quickly without risking data loss.
FAQ – Outlook “Trying to Connect” Issue (2025)
Why does Outlook work on web but not desktop?
This usually indicates a local Outlook profile or OST issue rather than a server problem.
Can VPN cause Outlook connection problems?
Yes. VPNs frequently block or delay Outlook’s connection to Microsoft servers.
Will rebuilding OST delete emails?
No. Emails are stored on Microsoft servers and will resync automatically.
