In general, this disclosure describes techniques of efficiently generating digital versions of financial documents from physical versions of the financial documents. As described herein, one or more financial documents may be inserted into one or more pockets of an envelope. The envelope is sufficiently transparent to allow both sides the financial documents to be scanned with a digital image capture device. Furthermore, the envelope is sized in such that the envelope, with the financial documents, may be individually fed into the digital image capture device by an automatic document feeder that is capable of feeding individual pages having a standard paper size into the digital image capture device. After inserting the financial documents into the pockets of the envelope, digital images of the financial documents may be captured. The digital images of the financial documents may then be processed and transmitted to a financial institution.