If I drag and drop multiple files into the drag and drop dialog only 1 will be upload.
If I click the browse for files option it also only allows for a single file upload.
Is there a configuration that needs to be changed to allow for multiple file uploads?
If you are using Confluence Cloud this behaviour is caused by a known issue where drag and dropping attachments to an Attachments macro will only upload a single file:
To workaround this, you will need to go to the Attachments menu when clicking on the 3dot button on your page. There, you will be able to drag and drop multiple attachments at once :)
This appears to have its own bug. For me, I have a page with an attachment macro containing 2 different files. If I go to that separate attachments screen, the menu item confirms by showing "Attachments (2)" but when I open it, it doesn't show any information about them. Not to mention, each attachment is separated by a HUGE amount of blank space, almost the entire page. I have to scroll down just to see the second one. But still, doesn't even show the names of these attachments.
There is indeed an attachment setting about the maximum attachments per upload. If you're an administrator, you can change it by going to the General configuration menu > Attachment Settings section:
If these settings are OK, I'd suggest to look at the following:
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