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The Twitter archive feature works by requesting an archive; once an archive is ready, receiving an email with a link to twitter, visiting twitter, and downloading the archive as a zip file.

Subsequently, in the user interface within twitter.com, the option to request the archive is changed to Resend email, and no new archive can be requested.

Would it ever change back to make it possible to request an archive again, to get all the updated tweets? When / how?

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Yes it does change back, not sure when it did, but it comes at least a few months since first request – Eight Days of Malaise Oct 24 '13 at 0:15

It would appear that a new archive of your tweets from Twitter can be requested every seven days or so.

Source: personal experience of now seeing a button to request an archive again, roughly 7 days after the date of the prior archive that has been generated.

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In my case, it took about 3 weeks for my request archive to become undimmed. I never got it to change to the resend email link. Using safari on a macbook pro running os10.9.1 with all updates applied. I also never got an email with the link in it containing the archive dl thing.

My source for this is also personal experience. Here is a screenshot of the current window from google chrome. https://www.dropbox.com/s/zzf4em8azouynfi/Screen%20Shot%202014-01-15%20at%2012.42.57%20PM.png

Hope that helps.

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