Outlook "CONNECT TO SERVER TO SEE THEM (Older files)" prompt is not working

Hi Christie Stephen DWP Commercial Finance, 

Welcome to the Microsoft Q&A Community. 

The message “There are more items in this folder on the server. Connect to the server to view them” typically appears when Outlook is running in Cached Exchange Mode, which only downloads a portion of your mailbox (e.g., the last 12 months). Older emails or items in shared/public folders may not be visible until Outlook connects directly to the server or the cache settings are adjusted. 

For your information: Only a subset of your Exchange mailbox items is synchronized in Outlook - Outlook | Microsoft Learn 

Here are several ways to resolve this issue: 

1. Set “Mail to keep offline” to All 

• Go to File → Account Settings → Account Settings 
• Select your Exchange/M365 account → Change 
• Move the slider for Mail to keep offline/Download email for the past to All 
• Click Next → Finish, then restart Outlook. 

2. Temporarily Switch to Online Mode 

• Go to File → Account Settings → Account Settings → Change → More Settings 
• Under the Advanced tab, uncheck Use Cached Exchange Mode 
• Click OK, then restart Outlook. 

3.Repair Sync Pipeline with /cleanips 

• Close Outlook 
• Press Win + R, type: outlook.exe /cleanips, then press Enter 
• Reopen Outlook to refresh the sync process and display stuck item. 

4. Create a New Outlook Profile 

If the issue persists: 

• Open Control Panel → Mail → Show Profiles 
• Remove the current profile and click Add to create a new one 
• Reconfigure your email account 
• Set the new profile as default using Always use this profile. 

For reference: Create an Outlook profile - Microsoft  

Please let me know if there are any updates. I'm happy to assist further whenever needed.

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