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I noticed the other day when one person in my chat list IM's me in Gmail, I don't get a desktop notification and all chats with him are not logged. At first I wondered if he was just off the record, but he couldn't seem to find anything that would be blocking me. We can still chat with each other, it just doesn't log the conversations.

His chats with other people and my chats with other people are saved. Does anyone know what setting we need to set in order to get chats between the two of us to be saved? We haven't (knowingly) blocked each other.

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You most likely set the chat with him to be off the record.

Chats that have been taken off the record aren't stored in your Gmail chat history, or in the Gmail chat history of your contact. You and the person you're talking to can both see when a chat is taken off the record, and you'll be notified if off the record mode is disabled. Your off the record settings will apply whenever you chat with this person, until one of you makes a change. Additionally, chats sent through orkut are never saved in chat history.

That assuming that both of you are Gmail users with a Gmail username, not AIM users using Gtalk.

Chat history is only available for users with a Gmail username.

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Neither of us have set our chats to be off the record, and we have double checked to make sure that wasn't the problem. –  dvcolgan May 30 '12 at 20:14

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