Add Attachment When Update Order Status?

[SD_Chris]

Hello,

Is is possible (either built-in or by any extension), to have a shop owner add an attachment when updating an order status and notifying the customer?
Orders -> <order number> -> Update Status (with Notify Customer checked)

We have a shop which deals with custom build orders for the customers, and the shop owner would like to be able to send images to the customer of their order while it is being built. Essentially sending them some "in progress" pictures which the order is being built.

We currently are looking at uploading pictures to a storage location such as Azure, Dropbox, etc. and then creating a short URL to put in the order comments. Other than the extra steps required for the shop owner, it also opens up some security questions to be handled to make it easy for the customer to click and view the images vs. having also the 3rd party storage site to login. Would be much easier for both the shop owner and customer if they could send attachments to the customer in an order update message.

Thanks in advance!