Stamps such as this are known from Babson Brothers envelopes with information on Edison Phonographs from around 1910.

All known stamps have been hand stamped because the envelope was to large for a machine cancel. From the one known cover which has a fold, it appears they were folded prior to being fed through the Schermack machine and then stuffed and sealed.
That is only an assumption. The envelope may have been folded after it had been received and opened.