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If I get to the point where I have spare time I will start slowly fixing the old systems. One (or at least one batch) at a time. I don't intend to modify everything but if I can take over the management of the basic infrastructure then at least that will be uniform across all systems. DNS, NTP, monitoring, backups, SA accounts,...
Resistance from co-workers is a big problem...
Legacy systems is another one but can be dealt with...
In some cases their are other issues though...
But equally it is not always possible to replace manual installations. I am not an Oracle DBA and in the organisation I work for the DBAs are a separate team. While it might be possible for me to automate Oracle installation and configuration, I don't know what to do, and I don't think that they would let me. (Heck, they don't listen when I tell them that asmlib is not needed, is a hack, and we should use the OS equivalent which is better supported)
Some of our installs could be automated, but when you only install the app once on two machines and the vendor supplied instructions are several hundred pages, I am not going there. If the vendor wants to automate their install process then great, but in that case I am not. (The application, database, message bus, DNS entries, file systems, network settings, etc are all detailed. The application alone consists of several hundred daemons and has its own registry...)
Finally I also have to deal with some systems which have been approved by a regulatory agency. Those ones cannot be changed without a lot more approval work. In those cases we are mostly at the mercy of the application vendor.
Indeed. I am talking about a large organisation (several hundred Unix/Linux servers alone, across five states, six major data centres) which has a lot of cruft, some very large, very complex applications, some federal regulation, and so on.
Even in this situation though we can introduce standardised server builds for all new servers, roll the infrastructure pieces under configuration management on (most of) the existing servers, and so on. Even if the applications look different on every machine (and some of those will be rolled out with the same configuration management tool, increasing as the apps get lifecycled) the operating systems themselves will become more and more uniform.
While it would be nice to be able to just rebuild everything it isn't always possible. But starting with one or two changes and rolling those out, then moving on to the next one might seem like small victories but over time they all add up. When you know that you can log on to a server and have standard tools and configurations it feels much better than not knowing who hand crafted the artisanal server you now have to deal with and what their preferences are.
Of course management likes the fact that I can roll out a new Linux server in 15 minutes compared to the old "two weeks" and they were all different.