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I have been using my THAT-1 for recording and it works great but when I try to send audio down the line it won't work.

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One of several things could be causing this problem. First you must send a line level signal into the "to phone" jack on THAT-1. Second, make sure the gray button is in the "in" position. This disables the handset microphone and enables the audio input. Third, the telephone you are using must have an "electret" type microphone in the handset. Not all telephones are the same and THAT-1 is only compatible for sending audio with telephones that have this microphone type. You may want to consider our THAT-2 which has a three position switch to allow you to use it with virtually any telephone.

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I would like to connect a THAT-1 between the wall jack and the telephone handset. Is that possible and do you have the connectors?

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Your THAT-1 doesn't replace your phone, but works in conjunction with it. You will need to plug it in between the telephone base and the telephone handset.

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What is the gray pushbutton on THAT-1 and THAT-2 used for?

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The button is used to select which audio signal will be sent into the telephone.
OUT = talking on the handset,
IN = sending audio through the RCA jack.
Keep in mind that you cannot send audio into the RCA jack and talk on the handset at the same time. However, any audio that is sent into the telephone can be heard on the handset and is available on the RCA output jack at all times.

$150 US