Why does outlook classic makes me click on inbox to sign in

Welcome Dan McDermott,

I understand how frustrating it can be when in classic Outlook for Windows, you are no longer automatically signed in when opening Outlook from the taskbar, and the sign-in only completes after clicking the Inbox, which did not happen in the past. 

To help resolve this as quickly as possible, could you please confirm the following details:  

• Are you signed into Windows with the same Microsoft account as the Hotmail account used in Outlook? 
• Have there been any recent Office or Outlook updates installed just before this behavior started? 

In the meantime, you can try the step to troubleshoot the issue:  

Option 1: Check Outlook connection status after launch  

• Open Outlook 
• Look at the bottom-right status bar and confirm whether it shows Disconnected > trying to connect, or Connected 

Option 2: Verify stored credentials  

• Open Control Panel from the Start menu 
• Go to User Accounts 
• Open Credential Manager 
• Select Windows Credentials 
• Remove any entries related to Outlook, Office, or MicrosoftAccount 
• Restart the computer and open Outlook again 

Option 3: Check sign-in experience inside Outlook  

• Open Outlook 
• Select File 
• Select Office Account 
• Confirm whether the account photo appears only after clicking the Inbox 

Option 4: Create a new Outlook profile if the issue persists  

• Open Control Panel from the Start menu 
• Open Mail 
• Select Show Profiles 
• Add a new profile and set it as default 
• Open Outlook using the new profile 

I hope this information helps resolve your issue. If you have any further questions, please don’t hesitate to contact me again in this thread. 

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