Advice/questions for my Imperial Stout brewday tomorrow

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TBC27

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Hi All. Looking for some advice/answers for an imperial stout I’m brewing tomorrow. Here is a link to the recipe - https://www.homebrewersassociation.org/homebrew-recipe/kaos-returns-imperial-stout/ . You need to be an AHA member to view this, I believe. If true, I attached a screen shot of my grain bill below.

1. When should I add the DME and brown sugar to the boil? Normally I add sugars towards the end of the boil for Belgians and IIPAs. 15 minute mark?
2. If I fall short of my OG, can I add more DME to boost gravity? When and how do I do that since I don’t measure OG until after cooling the wort?
3. I read somewhere that it is a good idea to hit the wort with a second round of oxygen 12 hours post pitch. Anyone do this and is it recommended?
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1. When should I add the DME and brown sugar to the boil? Normally I add sugars towards the end of the boil for Belgians and IIPAs. 15 minute mark?
2. If I fall short of my OG, can I add more DME to boost gravity? When and how do I do that since I don’t measure OG until after cooling the wort?

It doesn't matter much when you add the DME and sugar. If this was a light colored beer you would want to add the extract at the end of the boil to prevent some darkening but for a stout?? As long as the wort is still above about 145 degrees it will be pasteurized.

Adding DME to boost gravity is a decent idea. I'd dissolve it into a bit of boiling water first and then add the mixture.
 
If you add DME and sugar at the end of the boil, you will get slightly better hop utilisation too. I’d maybe just take off a litre or so of wort, then dissolve the sugar and DME in it before adding to the main boil.
 

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