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In past years I've done this after the tomatoes were planted. Next year I'll set it up before the tomatoes go in the ground.
Connect a soaker hose to a rain barrel. Lay the hose so that it leaks toward the plant. Fill the barrel and keep it filled. Add a quarter or less of a mosquito dunk. Keep an eye on the water. If anything is wiggling in there, empty it elsewhere (pump or bale) and refresh.
My plants are on a slight slope which I imagine makes good drainage.
Cover the soaker hose with 2 or more inches of straw to minimize evaporation from both the hose and the soil.
My tomatoes are in designed dirt with vermicompost castings, commercial mulch(Booster Blend of composted yard waste washed with dairy slurry ), and mushroom compost,(which is horse manure after mushrooms have been grown in it.)I think I'm going to have to pick the fruit today and ripen off vine. We got rain after drought.
BTW I recommend this site to everyone who visits my garden.
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