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Wash canning jars and lids in hot soapy water. Rinse. Drain jars.
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Wash tomatoes. Cut into sections and remove the stem end, core, seeds, and the watery/gelatinous sack around the seeds. Dice, or cut, the tomato pieces into small pieces (should equal apx. 9½ – 10 cups cut up). Place in large bowl and add the sugar. Let stand for three (3) hours to draw the juice from the tomatoes and allow the sugar to dissolve. Stir two to three times.
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Wash the lemons and orange well. Zest the lemons and oranges. Remove any seeds and cut lemons and orange into small pieces. Set aside.
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Using a slotted spoon, scoop out the crushed pineapple from the can. There is no need to thoroughly drain the pineapple in a sieve or colander but let most of the juice drip off the spoon for a few seconds before weighing out the 10oz of pineapple. There will still be some juice in the pineapple and up to a couple of tablespoons (no more) of the juice will be fine. Any more, however, and it would add too much liquid to the marmalade content, potentially causing issues getting it to set. Don’t be tempted to add any more than the 10 oz of crushed pineapple (with a bit of its juice) as, again, it may cause issues with the marmalade setting. Set weighed crushed pineapple aside.
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Fill a large-sized stockpot about two-thirds full of hot tap water. Fit stockpot with wire rack. Place the jars, on the rack, upright and in single layer, into the water. Use more than one stockpot if necessary to accommodate all jars needed for the recipe. Do not stack jars on top of each other in stockpot. Ensure the jars are fully submerged, each jar filled with water, and that the water is at least an inch over the tops of the jars, adding more if necessary. Cover, bring to a boil over medium-high heat, then reduce heat slightly and boil gently for 10 minutes. Turn off heat and leave the jars, covered, in the hot water to have ready to fill once the marmalade is ready.
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While the jars are sterilizing, transfer tomato–sugar mixture and the liquid to a medium-sized stock pot. Add the chopped lemons and orange and the zest, along with the crushed pineapple. Add the piece of cinnamon stick. Stir and bring to a boil over medium high heat, stirring frequently to prevent scorching. Immediately reduce heat and cook, uncovered, at a slow gentle boil until mixture thickens and reaches a temperature of 217°F - 220°F on a candy or instant read thermometer (see Note below for alternative method for testing marmalade doneness). Stir mixture frequently to prevent scorching. Remove and discard the cinnamon stick after about one hour, or slightly less, of cooking. Be patient, this cooking process can take awhile. Cooking the marmalade to a temperature of 220°F will yield a thicker marmalade but be slightly less pliable to spread than if it is cooked to 217°F.
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After the marmalade has been cooking for about 20-30 minutes, fill the canner about one-third to one-half full of hot tap water. Cover and bring to a boil to have it ready for the filled jars. Reduce heat to keep the canner water very hot.
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When the marmalade has reached its temperature, remove from heat and stir in the maraschino cherries, if using.
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Boil a kettle of water to have ready, if needed, to top up water levels in the canner once the filled jars are added.
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Use jar lifter tongs to carefully remove the hot sterilized jars from the water, one at a time, emptying the water from the jars back into the pot. Drain jars well and place upright on heat-proof board. Do be very careful as this is scalding hot water.
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Using a ladle, or a heat-proof glass measuring cup, and a wide-mouthed canning funnel, fill the hot sterilized jars with the marmalade, leaving about ¼” headroom in each jar to allow for expansion during the hot water processing. Remove any trapped air bubbles in the jars with a chopstick or small heatproof spatula. Add more marmalade to jars, if necessary, to bring marmalade up to ¼“ from jar rims. Wipe the jar rims with a clean damp cloth to remove any stickiness that could prevent the lids from sealing properly to the jars.
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Center the lids on jars so the sealing compound on the lid edges aligns with the jar rims. Fingertip tighten the ring/screw bands until resistance is encountered. Do not over-tighten.
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Using jar lifter tongs, carefully place hot filled jars upright in wire basket positioned in the canner, ensuring jars do not touch each other or fall over. If a canner is not completely full of filled jars, add enough hot empty jars to fill it to capacity to prevent filled jars from toppling over during processing. Make sure the empty jars are already hot as cold jars immersed in boiling hot water are likely to crack. Let the empty jars fill with water from the canner as they are submerged.
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Ensure the water level is at least 1” above the tops of jars, adding more boiling water as necessary. Cover with canner lid. Increase the heat to return the water to a full rolling boil then decrease the heat to just keep the water at a moderately rolling boil but not boiling over. Process jars in the hot water bath for 10 minutes, adjusting time as and if necessary for altitude. Start timing the processing from the point at which a full rolling boil is reached after jars have been added to the canner. At the end of the processing time, turn off heat and remove canner lid.
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Let jars sit in the hot water for 5 minutes then, using jar lifter tongs, carefully remove the jars filled with marmalade, one at a time, upright, and transfer them to a heat-proof cutting board, that has been covered with a towel, to cool completely. Listen for the “pop” or “ping” sound as the bottles seal over the next few minutes or hours. The lids of properly sealed jars will curve downward.
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Cover jars with a towel to keep light out and let jars rest, undisturbed, on counter for 24 hours. Then, test each jar for proper sealing by lightly pressing down on the center of each jar lid. If the lid is already pressed downward, and does not pop back up, it is properly sealed. Any jars that do not pass this test should be refrigerated and the marmalade used within a week or so.
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Store properly sealed marmalade bottles in cool, dark place and allow to rest for at least 1-2 weeks to allow flavor to fully develop before opening. Use marmalade within 1 year of bottling. Refrigerate marmalade once jar has been opened.