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“Watching it with my spouse, when Sam shows up at Bobby’s and Bobby tests him with the holy water beer, my spouse asked how Bobby knew. I wasn’t sure; except that Bobby kind of tests everyone and he’s very smart. It seemed that Dean did not get the chance to tip off Bobby because they made a big show of Meg/Sam cutting the phone line to Bobby’s…so he wasn’t tipped off. I think Bobby is just that smart; knew Sam was “off” and thought it was weird that he showed up without Dean. Maybe Sam and Dean never “stop by when in the area” as Sam said he was doing and that let him know.”
Interesting. I always thought that Dean did successfully get a call through to Bobby. At least we hear the phone ring a few times, then suddenly cut off. Bobby would’ve known that Sam had gone missing – I’m sure Bobby would’ve been one of Dean’s first calls for help. So I suspect that with Sam missing, a phone call abruptly cut off, and the suddenly dead phone line to the house would’ve been more than enough to make Bobby suspicious when Sam suddenly showed up at his door.