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I have the same bag-
and some sort of rigid item at the bottom
A flexible piece of plastic hacked out of an A4 ring binder at the bottom has helped loads. The mudguard should just make it all a bit easier and even more rigid.
It is definitely the downside to bikepacking bags compared to panniers. You need to concentrate when packing and it takes multiple efforts to get it down. Also not ideal when the temp drops and you wear everything. They like to be full.
Scrabble
@Bearlegged
Careful packing, and some sort of rigid item at the bottom of the bag (to stop the strap that goes through the saddle rails digging in) help. Also, if you can put multiple straps (at multiple heights) round the seatpost that seems to help. Has done wonders for my Alpkit tapered drybag (the cheapy version).