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Interested by the mention of evolution - has the seatpost strap on the saddlebag holster changed at all?
I did have one but sold it as I couldn't get the strap tight enough on the seatpost, so the bottom of where the holster rests on the seatpost would twist/slip sideways, so a) the bag was held at a funny angle, b) the side it had slipped to would knock into the back of my thigh.
Watching the video on the site it looks like that strap might have changed to wind around the seatpost once before velcro-ing, but I can't strictly remember what the one I had was like.
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Without seeing what you're describing it's difficult to say. There were some inconsistencies on early ones ( @spotter may have had a similar issue to you ) with the length of the Seatpost strap. This has been addressed and all velcro pieces are now being pre-cut to ensure they are to specified length and consistent.
It's a case that Nathan (the guy behind Restrap) makes stuff, rides it then looks for niggles/ways to improve it. He also has a load of mates that abuse the stuff and give feedback, plus he listens to what customers/users have to say.
Sorry to hear yours didn't work as expected, it's always worth contacting them if you do have issues, sometimes it's down to user error and sometimes down to a manufacturing slip up, but they'll always do their best to help out either way.
Hope it serves you well. Nathan's goal is to make kit that works well and lasts. Each bag has been through a massive evolution over the last couple of years, but with very small incremental changes. Rather than just sticking to a design and churning it out he's constantly looking to improve on things. Would love to hear how you get on with the setup and see a pic of the loaded bike.