I went back to WRACo Vol 1 again.  There are line drawings of the 220 grain FMJ bullet seated in a Krag case.  The drawing shows the crimp in the bullet cannelure and the tiny "w" visible just above the cannelure.  The round nose of the bullet does not, to my elderly eyes, quite match the bullet in the photo and I also have very minor doubts about the copper-colored bullet.  I looked at WRACo loaded cartridges in my collection (other calibers) and the "w" is visible.

All the Winchester labels came from the Winchester art department.  There is a product number on each.  My understanding is that the "8-30" on the label is a date showing when that particular label was approved for use by the Winchester bureaucracy.  We can infer that the box went into the Winchester product distribution system after that date.  It may or may not tell us much about the age of the contents.

W R A (no dots) and a 2-digit year code was specified as the headstamp for Winchester cases made for a government contract.  I think it is possible that the WRA 30 cases loaded for a late Navy contract would go into a box like that, especially since Frankford Arsenal was loading Subcaliber cases at the same time.  FA used the M-1 bullets for the .30-06 because they had used up all the Krag and .30-03 bullets in stock and would make no more.

Those boxes of Western Cartridge Company 180 grain boat-tailed bullets are very interesting.  They are from the post WW1 to pre-WW2 period when long range military style shooting was in vogue.  WRACo loaded the same sort of load, but their labels indicate that the loaded cartridge is too long for a Krag magazine and is intended to be single-loaded.  I expect that there were rifles purpose-built, and maybe not Krags, for that cartridge.