The only way to upload the supporting  attachments is to have them somewhere on your drive that you can access them and then manually upload. 

I would be surprised if it did. Remember that the LEDES1998B standard has not changed since 1998. It would violate the standard to include the expense receipt PDFs within the same file.

When you upload them to the audit houses, it is usually two different areas. One for the LEDES file and another for the receipts. Because you don't want to submit the PDFs to the same format standard as the LEDES file. They would fail.

Now, technically you asked if you could upload them "along with" the DAT file. Yes, if your audit house allows it. See this screen shot of Legal Tracker:

Note that the first Browse is for the DAT file and the second is for the supporting receipts. But it is still two different kinds of submission.

Which brings us to Caren2's response about locating the PDFs quickly and easily when you have supporting documents. 

Hope that helps.

Nancy Duhon, Esq.
Duhon Technology Solutions, LLC
Master Certified Consultant for Sage Timeslips
Providing individual Consultations and Third Party Remote Desktop Support - including older/unsupported versions.
404-325-9779
[email protected]

And as Nancy points out, that is how Legal Tracker does it on their specific website.  With the myriad of different EDI Providers, it would be a big challenge for anyone to be able to keep up with the different providers and their internal processes.