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Date: Thu, 8 Apr 2021 15:53:49 -0400
From: bzs AT theworld DOT com
To: Andy Romens <Romens DOT Andy AT hotmail DOT com>
Subject: Re: Questions on how to upgrade Apache
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I upgrade apache from sources all the time tho not on cygwin, we use
Linux for that, but the basic idea is the same. My advice, having
looked over other advice here, and your responses:

1. You probably don't want to go to another web server like nginx just
for what you describe.

You would have to reconfigure your entire web server environment
including hosts, server certificates, dependent software (e.g., do
your sites use php?), etc. That can be much more work and subtlety
than just upgrading an apache dot release.

2. Although building apache from source is not very difficult there
are build configuration options and even dependent software (I dunno,
fastcgi, whatever) you would need to navigate.

If you could get the exact build configuration (./configure
...options) that cygwin uses that might make it a lot easier.

That result might "just work" since you're only trying to upgrade a
dot release.

But there may be other issues such as dependent software and
dynamically loaded modules. Fortunately the configuration files
(*.conf) between dot releases should just work, they don't change much
if at all for the releases you describe.

Given their configuration options it might be worth a try if you have
the time and testing environment.

3. But then the pottery shop rule would kick in, you break it, you own
it.

By which I mean where do you go forward from there? Future releases?

You will probably have to build from source forever or find some way
to backtrack back into the binary cygwin releases. For us building and
configuring from sources is fine but TBH on a scale of 1-10 I am an 11
on these things (pardon my modesty :-)).

4. Probably the best advice is:

a) examine why someone thinks you need to do this at all other than
they just like to run the latest and greatest. If it's security flaws
consider that errors in doing this from source or going to another
server entirely could be much more security-error-prone lacking
in-house expertise.

b) If they have such exotic and exacting requirements that they can't
tolerate being behind a few dot releases then they should be willing
to pay an expert to help them meet those requirements (no I'm not
available.)

In all seriousness and apologies to the cygwin crew who I love and
admire the very fact that you're running apache on cygwin makes me
think your requirements can't be too pie-in-the-sky, I'll guess you're
not running Amazon or Shopify etc.

c) Seriously consider a pre-built native Windows apache release.

That should pretty much drop-in and if that seems too difficult the
other options like building from source or switching to another server
will likely be much more difficult.

d) Apply to law school.

-- 
        -Barry Shein

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