Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello
Since the Work Offline button will not turn off, please close Outlook, press Windows + R, type outlook.exe /safe, and press Enter.
Try turning off Work Offline in Safe Mode. If it works there, disable the Outlook add-ins under File > Options > Add-ins.
If it is still stuck, create a new Outlook profile instead of deleting the current one: close Outlook, open Control Panel > Mail > Show Profiles > Add, set up your email account, and select the new profile when Outlook starts.
Microsoft’s instructions are available here:
Please also confirm whether the status bar says “Working Offline,” “Disconnected,” or “Trying to connect,” as the latter two usually indicate an account or mail-server connection problem rather than the Work Offline setting.