Outlook Stuck on “Trying to Connect” or “Disconnected”? Fix It Fast (2025 Guide)

Outlook Stuck on “Trying to Connect” or Showing Disconnected?

If Microsoft Outlook is stuck on “Trying to Connect” or keeps showing Disconnected, you’re not alone. This is a very common Outlook issue in Windows 10, Windows 11, and Office 365 — and it usually prevents sending or receiving emails.

The good news? In most cases, this problem can be fixed quickly by following the right steps.

Common Symptoms of the Outlook Connection Issue

• Outlook status shows Trying to Connect
• Outlook shows Disconnected at the bottom
• Emails stuck in Outbox
• Outlook freezes when opening
• Office 365 Outlook keeps going offline

Why Outlook Gets Stuck on “Trying to Connect”

This issue usually happens due to one or more of the following reasons:

• Internet or network instability
• Corrupted Outlook profile
• Faulty Outlook add-ins
• Incorrect proxy or VPN settings
• Damaged OST or PST file
• Office 365 authentication problems

Fix 1: Check Outlook Offline Mode

Sometimes Outlook is simply set to work offline.

• Open Outlook
• Go to Send / Receive tab
• Make sure Work Offline is NOT enabled

Fix 2: Restart Outlook in Safe Mode

Outlook add-ins are a very common cause of connection issues.

• Press Windows + R
• Type outlook.exe /safe and press Enter

If Outlook works fine in Safe Mode, disable all add-ins and restart Outlook normally.

Fix 3: Disable VPN or Proxy Temporarily

VPNs and proxy servers often block Outlook from connecting to Microsoft servers.

• Turn off VPN
• Open Control Panel → Internet Options → Connections → LAN Settings
• Uncheck Use a proxy server

Fix 4: Create a New Outlook Profile

A corrupted Outlook profile is one of the top reasons for this issue.

• Open Control Panel → Mail
• Click Show Profiles
• Add a new profile and set it as default

Fix 5: Repair Microsoft Office

If Outlook program files are damaged, repairing Office usually fixes it.

• Open Control Panel → Programs
• Select Microsoft Office / Microsoft 365
• Click Change → Quick Repair

Still Stuck? Get Expert Outlook Help

If Outlook is still stuck on Trying to Connect after trying these fixes, the issue may require advanced troubleshooting like mailbox repair, authentication reset, or server-side fixes.

Our certified Microsoft Outlook & Office 365 experts are available 24/7 to help you get back to work quickly.

Call now or chat on WhatsApp for immediate assistance.