after removing the plug you dont want to fill the hole with silicon.... there are some intricate pathways built into the mess that channel the water to where it needs to go. blocking these areas with silicon is not going to help your situation.
after removing the plug just smear a coating of sealant onto the rear portion of the plug and shove the entire thing back in place... being careful of how it is supposed to be oriented inside the channel.
then just wipe off the excess sealant that gets left exposed after re inserting the plug.
the way you did it you have no idea where or how much silicon you have blocking the inside of the channel.
I would pull the plugs, clear everything out and try again.