I was caulking my bathtub and was removing the caulk around the overflow plate when the linkage for the plunger came loose. I removed the linkage put the plunger back down the hole but now then the tub wouldn't hold water even when though I could hear the plunger bottom out.

I took the overflow pipe off and discovered that there is a lip on the pipe that the plunger is bottoming out on and I can't get the plunger past this point. I included a pic of where the plunger is bottoming out on the pipe.enter image description here I cleaned up the lip with a wire brush and file and greased the plug with plumber's grease and still no luck. I bought a new plastic plug and was able to get it past the lip but broke it in the process.

The tub held water for 10 years so I know the old brass plug worked. I feel like I am missing something easy in my assessment of this issue. Any thoughts out there?enter image description here

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