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From: doug <doug@fledge.watson.org>
To: "bsd@todoo.biz" <bsd@todoo.biz>
Subject: Re: Upgrading from 7.4 to 9.1 
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On Sat, 27 Apr 2013, bsd@todoo.biz wrote:

> Hi,
>
> I wanted to know if you would consider updating from 7.4 to 9.1 directly ?
>
> Has anyone tried that with success ?
>
> I plan to use the freebsd-update method.
>
> Thanks for your feedback.
>
> G.B.

If you are not a developer (I am not), I think the short answer don't do it. I 
think the issue is leaving stuff behind that might hurt. Eventually would be 
much worse than immediate problems, especially for a remote server.

My experience with freebsd-update has been if a mirror has the diff, then it 
will work. That said, I have never skipped a version. Earlier threads on this 
topic suggest its better to go to 8.0-rel then to the latest 8.x then to 9.

For me I used CD/DVD even though it meant a drive. I would not be too suprised 
if freebsd-update balked at skipping 8. If you are physically with the system, 
it will not take too much time to try it. The process of a minimal install from 
CD then freebsd-update is not very long. If you are running Xorg, it is the only 
way IMO.