Automatic Send/Receive Not Working in Outlook

Automatic Send/Receive Not Working in Outlook 2016

Method 1:

1. In Outlook "Sent/Receive" at the bottom of the listing you will find the option  Disable Scheduled Send/Receive.
   
2. Once the option has been enabled (there is no check box next to it), your auto Send/Receive should start working again. There is no need to restart Outlook.
   

Method2:

Outlook 2010 and later versions

To resolve this behavior, create a new Send/Receive group in Outlook:  

1. Click File, and then click Options.
2. Click the Advanced tab. 
3. In the Find Send and Recieve section, click Send/Recieve.
4. Under Group Name, click the group, and then click Copy.
5. Under Send/Receive Group Name, type the new group name, and then click OK.
6. Under Group Name, click the old group name.
7. Under both When Outlook is Online and
   When Outlook is Offline, click to clear the check box for
   Include this group in Send/Receive (F9).
8. Click Close.
9. Quit Outlook, and then restart Outlook

Method3:

Remove/disable Outlook Add-on

Reference:

https://www.zubairalexander.com/blog/automatic-send-receive-not-working-in-outlook-2016/