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I am running Debian testing. My sources.list is:

deb http://ftp.us.debian.org/debian testing main

When Wheezy comes out (testing becomes stable), will testing automatically point to the new Jessie distro (so to update all I need to do is aptitude update && aptitude upgrade) or will I still need to dist-upgrade?

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Testing will always point to the current testing. You do not need to change anything if you wish to stay on testing. The only time you would need to change to remain on testing is if you specified the release by name eg:

deb http://ftp.us.debian.org/debian wheezy main

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