You can use our Add-ins Management Tool to enable / disable add-ins and see which one causes the offline mode problem (available for free within Bells & Whistles for Outlook – among with other +40 productivity enhancements for Outlook).
A third party Outlook add-in might be causing Outlook to stay offline. Your Outlook profile might be corrupt – try creating a new Outlook profile and see if it solves the problem. Your email login credentials are not correct. 
Outlook can not reach to your email server (your Internet connection is not reliable or it is not properly configured). If Outlook is working offline no matter if you disabled the Work Offline mode, then most likely there is a problem with your Outlook setup. The Work Offline button should now be visible on your Outlook Send / Receive tab. Important: there is a small bug on the above checkboxes! Even if you previously unchecked the option “Use Cached Exchange Mode”, Outlook will still show it as being checked! So Outlook might show that this option is checked, but in fact it isn’t 🙂 To make sure you actually enable the cached Exchange mode, you need to uncheck, then re-recheck the cached Exchange mode, then click on the OK button until you exit the options windows, then restart Outlook. On the popup window, click on the Advanced tab and mark the checkboxes “Use Cached Exchange Mode” and “Download shared folders”:. From the Account Name and Sync Settings window, click on the More Settings button:. From your main Outlook window, go to the File -> Info Menu -> Account Settings -> Account Name and Sync Settings:. If that is the case, here is how to fix the Work Offline button: However, the Work Offline button might be missing from Outlook even if you are using an email account capable of working offline. Usually, this button is missing because your email account is not using a mail server compatible with Microsoft Exchange. It may happen that your Outlook window is missing the switch button to work offline – online. 
Missing “Work Offline” Button – How to Fix it To switch from the offline to the online mode, simply go to your Outlook Send / Receive tab and locate the “Work Offline” button: click on it to switch between the online and the offline mode: Outlook Is Working Offline – How to Switch to Online
Instead, it will wait to be switched to the online mode and only then it will send & receive emails. If Outlook is working offline, it will not receive new emails and it will not send emails that you’ve prepared to be sent. Starting with Outlook 2010, Microsoft introduced the ability to work online or offline for email accounts that use Microsoft Exchange servers (for example, email addresses created at ). This article describes how to fix Outlook when it’s working offline: switching from offline to online mode, missing “Work Online” button and the potential reasons why Outlook keeps getting offline.
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