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People change jobs or change email. So we need to update their contact details in Gmail. Does Gmail keep track of the old email addresses behind the scenes?

I have always kept the old email addresses in contacts so that when I want to show "recent conversations" I get a full history. This works, but it also means I need to make sure I don't select an old address when emailing them in future.

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No Gmail will make a duplicate contact out of it, which you will have to merge 'manually'.

Luckily this is a very easy process, though it may take some time if you don't keep up with it.

Gmail even helps you find duplicates if their name doesn't change much. Else you just have to select them both and click [Merge]

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Useful info, and something that I wasn't aware of. But that can leave me with a contact with 10 email addresses, only two of which are "live" and all of which get presented as possible addresses when composing new. –  itj Aug 10 '10 at 12:53
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