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Since the winterizing port is not used much perhaps the check valve was stuck shut. Mine has done it before. Just stick a small screw driver in the port and unseat it. Also ... many of us have had to use 2 hose washers in the winterizer port as one just doesn't seal it up well enough. I used to be the "pink stuff" guy as well, but the past 3 years, I've went solely with air and then pouring a quart of antifreeze down each sink/tub trap. Works for me ...
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