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You may want to change the filter to a spin on as the square filters take forever to fill by cranking the starter. The spin on ones can be prefilled! Look in Walmarts boating section there is a kit with the block and filter for around 30$:-D

You could try putting trans fluid in a spray bottle remove the air cleaner and fog the intake while someone turns over the starter. When I had a problem getting my filter to charge I did this and kept it running long enough to fill the filter and IP.:-D

Once you pull the filter it will take quite some time (cranking) for it to refill with diesel. You may choose to replace it with the walmart setup (30$ in the boating section) it offers a spin on filter and thus you can prefill it. This make filter changes a breeze.