Quoting "Richards, Toby" <toby.richa...@slo.courts.ca.gov>:

> Will pkg_add -ui upgrade between major releases, such as php 5.2.x =>
> 5.3.x?
> When I upgraded OpenBSD 4.9 => 5.0, there was a huge issue because
> it supported both PHP 5.2.x AND 5.3.x. I'd have loved to seamlessly
> upgraded to 5.3.x, but the support of both made it nearly
> impossible.

PHP 5.2.x and PHP 5.3.x are different streams of PHP - you can't assume that a
PHP 5.2.x code base will work on 5.3.

http://www.php.net/manual/en/migration53.incompatible.php

So, no, something major like that needs a bit of thinking, regardless of OS.

You'd be up the creek without a paddle if your X hundred websites based on some
PHP 5.2 feature stopped working with PHP 5.3, wouldn't you?

I've been upgrading FreeBSD and OpenBSD for the last few years (base +
ports/packages) and both have been absolutely rock solid ... sometimes there's a
little more thinking required on the administrator's part first - the system
can't guess your intentions.  You want to be on MySQL 5.1 or 5.5?  PHP 5.4? 
Apache 2.4?  I don't want the upgrade making those choices for me ...
> 
> 
> Respectfully Submitted,
> R. Toby Richards
> Network Administrator
> Superior Court of California
> In and for the County of San Luis Obispo
> (805) 781-4150
> ________________________________________
> From: Mike Erdely [m...@erdelynet.com]
> Sent: Monday, May 21, 2012 7:05 PM
> To: Richards, Toby
> Cc: misc@openbsd.org
> Subject: Re: Upgrading OpenBSD
> 
> On Mon, May 21, 2012 at 9:43 PM, Richards, Toby
> <toby.richa...@slo.courts.ca.gov> wrote:
> > OpenBSD does have an Upgrade
> > option, but does it upgrade the installed packages?
> 
> pkg_add -

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