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So this new kegging setup is the best thing I ever purchased, beers are fresh and so full of hop oomph from first to last glass. However now I am having a very hard time translating that into bottles. It seemed when I was priming in the bottle things weren't nearly this bad, where could I be going wrong?

I have just finished a digital ipa clone, really great beer... Hops that zapped your taste buds for hours and really was a pleasure to drink from the keg. I bottled the last 5 litres and popped them in the fridge. No more than two days later the beer tastes very average, hops have all but gone, and this was a really heavily hopped brew. And the beer tastes like caramel. There was no to very little diacetyl present before I kegged, (did the old warm up and sniff test and everything was fine).

Is it oxygen? I fill my bottles with a racking cane and a stopper, just pressing the stopper to release the pressure... However I don't have any means to purge the bottles of oxygen at this point.

I clean my bottles with a home made pbw mix and rinse well with starsan... No off flavors or anything from that.

Would a counter pressure filler fix my problems? Is there a cheaper option?

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I just fill bottles from the keg using a picnic tap and have no issues.  The beer is around 5C, the serving pressure is very low, just enough to get the beer moving.  I tilt the bottle and fill it slowly.  Once filled to the desired level I give the bottle a gentle rocking to form a head that rises up to the top of the neck pushing out the O2 and filling the space with CO2 bubbles.  I then cap it before the foam falls away.  Works well for me.

What's the bottled carbonation level like in comparison to draft? it could be that slightly lower carbonation in the bottle is dulling the hop character?

I use the same method as you, and as far as I can tell you get the best results bottling from the keg by keeping everything super cold. Stick the bottles in the freezer, refrigerate your bottling gear. Ideally, bottle the beer at 1C and slightly over-carbonate to make up for any lost CO2 (though that's not always possible if you're just decanting a rigger to take somewhere). 

Oh, and always cap on foam so there's minimal oxygen in the headspace. 

I do run the carbonation in the keg a bit higher to bottle, probably close to 2.9 volumes.... I do find that I lose a lot of carbonation in the bottle. So running it higher leaves the bottles carbonated perfectly. However I dont cool the bottles when I'm filling them

Thanks for the link Stu.... I had been pulling my racking cane out and just capping with a little space left in the neck... Hopefully thats the cause of it. I must say I am surprised at the massive difference such a small amount of oxygen can make to a beer... The aroma's just disappeared and the malt went from candy sweetness to caramel in no time at all

http://inibrewsupply.com/beer-gun/

works perfectly for me!

CO2 purge and nice filler.  get the accessory kit from him too.

INI is in Nelson.

I had made contact with Ini some time ago asking about when the beerguns would be in stock again, they couldn't tell me when they would be back in stock. And I never heard from them if indeed the restocked 

Im happy with the racking cane and stopper, seems to work fine apart from my oxygen issue.... But Ive filled a few bottles this weekend making sure to fill right to the top and cap on foam. Well see if that fixes things. I don't know how fast beer can absorb oxygen but if that small amount of contact time while the bottle is filling makes a difference then I will look into splitting my gas line and attaching a release valve for injecting some co2.

Looking back on how I was going about it, I imagine that the space in the neck which was filled with air was the culprit.

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