envelopes & texts - morning of the 17th; envelopes left in the Winchester & co house kitchen; After the locksmith comes to rekey all the locks following Sam losing his keys, envelopes - for Mary, Dean, Sam, Heather, Bobby, Harry, Ben, Claire, Faith, Jo, Ruby & Castiel - are place on the kitchen counter with copies of the keys to parts of the house relevant to the individual (front door, back door, side doors, weapons room or other places, depending on what Sam had on his keychain), to be picked up when the individual is next in the kitchen (or dropped off if other arrangements are made).
text to Jo; Had to rekey the locks, you'll need to come get a new key to replace your old one.
text to Ruby; Assuming Castiel still has his old key to the back door of the house. Had to rekey the locks, so next time you're by, pick up a new one so you have it for when Ben's with you.
[ooc: This is working on the assumption that all house residents AND anyone who stayed more than one night at the house (Jo when she was often there; Castiel when he was human, which was the key shared with Ruby; Faith when she was there for a few nights; Claire being there now) have at least one key and some of them likely other keys as well.]