Orders will only be reflected on the dashboard chart if they have been invoiced.
In addition, I see that you have custom order statuses. The only order status
that will be counted in the reports, without customization, will be Processing,
Pending, Cancelled, and Closed. All of your orders have using a custom status,
which is why they are not being counted in the report.
In order to have the orders with your custom order statuses reflected in the
Magento report, you will need customizations, which fall outside the scope of
support. Customizations can be done through an engagement with our Expert
Consulting Group (ECG) or one of our Solution partners. Please let me know if
you would like me to put you in touch with ECG.
So it is possible but I have not been able to figure out how.