I've got a gentoo server here. It hasn't been upgraded in a good long while. I just tried to emerge a package, and it tries to download things, but all fails with 404. I can get other web access fine.

Do I need to do an emerge --sync?

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The ebuild is most likely pointing to an old file that has been removed. An emerge --sync should fix the problem, but if it doesn't you can try downloading the file manually and placing it in /usr/portage/distfiles

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maybe your GENTOO_MIRRORS line in /etc/make.conf is out of date? check that the mirror is still active?

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