I asked a question looking for pointers to overview materials about VPNs, as opposed to product-specific documentation. It was very promptly closed as 'off-topic' on the grounds that "Questions seeking product, service, or learning material recommendations are off-topic", with a link to a post about shopping questions.

Now, it's clear that shopping questions are largely pointless – they're over-specific and they date quickly – but all of the rationale connected to this 'off-topic' reason is connected with the 'shopping' issue; I can't find any rationale at all about learning materials. I see that the relevant FAQ initially just mentioned shopping questions, so the 'learning materials' phrase was clearly added later. Similarly here.

The only relevant link I can find is here, which says "we consider education, something all sysadmins should be doing constantly, to be off-topic." That explanation might need ... a touch more rationale. I observe that no-one, in the last year, appears to have felt moved to supply the requested explanatory link.

So I'm still rather in the dark. What's so bad about learning?

  • 2
    Also, due to the speed of how quickly stuff moves in the IT world, information goes out of date quickly. There's no point providing out-of-date information or info for much older versions (MS knowledge base, I'm looking at you.)
    – tombull89
    Commented Jun 24, 2014 at 13:01
  • 3
    Learning isn't bad, allowing questions about what to read to learn is. Important distinction there. Commented Jun 24, 2014 at 13:02
  • 1
    @tombull89 I agree that parts of MS's documentation would benefit from making finding equivalent information for other versions easier, but knowledge base articles on legacy software retain value until the last people stop using them. Commented Jun 24, 2014 at 17:35
  • Let me link to my answer that helps define shopping questions here on SF meta.serverfault.com/a/6488/7861 that may help to some extent.
    – TheCleaner
    Commented Apr 11, 2015 at 5:04

8 Answers 8


Server Fault (specifically) does not "do" learning material requests. We try to focus on questions that have a specific answer to them, and Where/How can I learn more about technology X? doesn't fit well. Unless "lists of resources" are well curated they turn to shit, and the value of the site is hurt by that.

A better approach would be to ask and answer your own "How do VPNs work?" question, in the style of our IPv4 subnetting or IPv6 subnetting questions. This makes Server Fault the focus for learning, rather than just an empty signpost saying "Go buy/read this material".

You would need to provide an answer of the same breadth and depth as the subnetting questions for this to be truly useful, which means you would have to do the legwork to find the resources and write up the summary (Chat can help within reason - we won't do all the research for you, but if you want to embark on writing this kind of in-depth answer and have questions I'm sure folks would be willing to help clarify any points you need help on).

Note that other Stack Exchange communities have different views on the subject.
Stack Overflow has allowed the C++ Book List to live, and Aviation is experimenting with the idea as well.

For Server Fault in particular we've found these types of questions tend to do poorly (because nobody wants to curate them), so we generally don't allow them.

  • 1
    +1, for ask and answer the question yourself and make SF the focus for learning. Also, I've came across the SO C++ book list, EE I believe has something similar. If it were a single Book question personally I wouldn't be opposed to it, but It'd have to be all inclusive for every tech, not a question for VPN, a question for Windows Server, a question for Exchange, a Question for RHEL, all for books, that's insane. That might not be bad, but if no one wants to curate them then that's a different matter.
    – MDMoore313
    Commented Jun 24, 2014 at 14:53
  • However, the answer on SO for that question has only been edited 12 times in 5.5 years, which strikes me as weird because the question itself has been edited 90+ times.
    – MDMoore313
    Commented Jun 24, 2014 at 14:54
  • @BigHomie That question has also been locked, unlocked, had people edit answers into the question, had multiple answers over its life, etc. -- it's a damn mess, and the war the SO C++ community has had to fight to keep it from degrading into a total clusterfuck is part of why we decided not to allow that sort of thing here. Sysadmins are WAY too lazy to curate a question like that. (We have exactly one that I can think of))
    – voretaq7
    Commented Jun 24, 2014 at 15:01
  • I can't say I'm persuaded, but +1 for a very direct answer to the question. The 'canonical answers' are interesting and surely useful (thanks), but could perhaps be better signposted on the faq tag page: perhaps "Here are some canonical questions and answers" would be a better title to this question (I examined the faq tag before and didn't register this as a useful link to follow). Also, having a link to the FAQ on the front page would be useful, but I appreciate that might need SE cooperation. Commented Jun 24, 2014 at 15:24
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    @NormanGray The concept of "canonical questions and answers" isn't well supported by the Stack Exchange system. We've talked about adding a canonical tag to these in the past on the main site to help people discover them.
    – voretaq7
    Commented Jun 24, 2014 at 15:30
  • Hmm: that canonical questions page is also linked from the on-topic page, rather obviously in retrospect. I'm wondering why I didn't register that when I read that page before (it wouldn't have answered my question, but I would have been pleased to find that). All I can think is that 'common questions' isn't the magic word: 'frequently asked questions' is magic. Commented Jun 24, 2014 at 15:30
  • @NormanGray If you would like to propose some wording changes to the on-topic page (or other parts of the help center) open up a separate meta discussion - we can edit those pages, but editing them generates a lot of back-end notifications to the Stack Exchange community team, so we like to edit them infrequently and make sure we get the changes right the first time...
    – voretaq7
    Commented Jun 24, 2014 at 15:32
  • @voretaq7 done. I've tagged it 'feature-request', rather arbitrarily. Commented Jun 24, 2014 at 16:15

I think this may be confusing for a new person to grasp, it was hard for me to grasp as well. I'll do the best I can.

We want to attract experts

The main site ServerFault.com has specific guidelines on what types of quesitons can be asked by the community, which is governed by the community. There are a lot of reasons for this. Mainly, this site wants to attract experts in the field. To do that, when the said expert visits the site, she does not want to have to peel through questions about

  • What books are good for learning about VPNs?
  • How do I set up a VPN?
  • What does 'VPN' stand for?
  • When would I use a VPN?

These are basic questions that a VPN 'expert' would typically know already. Now, a site with VPN experts would naturally attract VPN beginners looking to get some advice. Please realize that

Beginners are encouraged to come as well

However, asking questions without researching first is not respecting someone's time, and makes one look bad (more on that later). Search engines have come a long way over the past 20 years, and there is a Wikipedia article on pretty much everything. Also, try searching the main site for the vpn tag, chances are someone has asked a couple of basic questions in the site's history that will supplement Wikipedia or any book you read.

That book sucks

Next, everyone learns from different books in different ways. What may be a good book for one person, may not be a good book for another. This will lead to biased voting on any said questions, long comment chains, and general flaming. Granted, the community is good about cleaning this stuff up, no one wants more work for themselves, as our mods are a part of the community. A general rule of thumb is: Chatty questions should be taken to chat, and product recommendations, books or otherwise, are chatty questions.

Most here are not Anti-n00b

I haven't talked with anyone here I can remember that is against an OP that is learning a new technology or (dare I say it) helping sysadmins in an area that is new to them. As a matter of fact, one must continue to learn new technology in this industry in order to stay current, valuable, and marketable. One main thing that separates a professional sysadmin from a wannabe though, is the professional spends their own time first to actually research the problem or new topic. Among other things, it's a bad look when another admin can type your exact error message (or question) in Bing and the first result solves your problem (gives you an answer). I know from experience, most learning questions can be solved using $SearchEngine, and if/when you come across conflicting information, then it's time to take it to the experts for clarification. It's all about helping yourself first.

Now, that should answer this meta question about why 'learning materials' being off topic. As for your book question, feel free to take it to the chat, if you're brave enough. Muha,MUha,MUHAHAHAHAHHAAAAAA.

  • Sure, I take that general point, which is precisely why I made clear in the question that I already know how a VPN works in principle, what (I thought) was weak about the Wikipedia article, and why the existing questions and answers here weren't addressing the problem. I intended to indicate also why book-length resources weren't useful, but I don't think I communicated that well. But my question (and your answer) is about the general category rather than my specific question, so this comment may not be relevant. Commented Jun 24, 2014 at 13:49
  • Yeah I tried to generalize as much as possible since you asked a great general question for meta, imho. I have to admit I didn't ready your original question though
    – MDMoore313
    Commented Jun 24, 2014 at 13:55
  • Heh: I tend to go with my hard-won Usenet intuitions for (technical) questions. But since we're now (gasp!) into the third decade of Eternal September, that may be wearing thin.... Commented Jun 24, 2014 at 14:41
  • I have to disagree with the "beginners are encouraged" as well as "asking questions without researching first is not respecting someone's time" to the first, I long ago stopped recommending new admins go to SF as a source of answers because the questions they were asking kept getting shunted to SF or rejected. As far as wasting time- which is less respectful "wasting" your time with a question you know the answer to off the top of your head or making one spend an hour "researching" a topic that you could have simply answered in potentially minutes- I find the latter far more disrespectful
    – Jim B
    Commented Apr 6, 2015 at 18:45
  • 1
    One can be an expert system administrator without knowing every product a system administrator may need to touch. I don't think the questions asked by an expert system administrator about a product completely new to him would bother other experts. Questions fitting that criteria would likely be much higher quality than those written by a person with no system administrator experience whatsoever, but they may still be very basic.
    – kasperd
    Commented Apr 6, 2015 at 18:49
  • @JimB you're assuming that googling something to that someone else knows the answer to already would typically take an hour, when that may or may not be true. Also, I've said nothing regarding beginners and researching first that isn't in the help documentation. I asked my first question on the network after searching through to the bowels on the internet (yes, for hours) and not finding anything relevant.
    – MDMoore313
    Commented Apr 6, 2015 at 19:26
  • This was a very specific topic and if someone knew the answer off the top of their head (to be specific this was very new technology so very little was available on the 'net but I did my due diligence anyway) then we've done the internet a great service, as it wasn't readily searchable until then. However, no one offered an answer, but I didn't give up, eventually when I found the answer I posted it myself, thus contributing to the 'cause. Jim, I can't speak for everyone, but a lot of long-timers (I don't count myself in that group, but I feel the same way) on SF are tired of the low quality
    – MDMoore313
    Commented Apr 6, 2015 at 19:27
  • questions being asked here in general, it's much easier to go to google and type in a question and search than it is to create an account here, post a question, wait for someone to spoon feed you an answer. We don't have to look too hard for examples of that. I do stand by my answer though in that most here don't shun n00bs, nobody shunned me, but then again I read the faq first, so maybe that's it.
    – MDMoore313
    Commented Apr 6, 2015 at 19:27
  • Here is a perfect example, serverfault.com/questions/680490/… . Clearly I don't think that there would be disagreement that this is an enterprise admin task, looking at the question there is a long explanation of what was done and how best to proceed, based on what he knows, and yet, not only was question put on hold for not demonstrate reasonable business information technology management practice ",
    – Jim B
    Commented Apr 9, 2015 at 21:51
  • (somehow the completion comment didn't post) But in frustration the op asked to have it deleted. This user used what he knew and asked a reasonable question. Because he didn't know (and actually asked) what he should be using - he was downvoted.
    – Jim B
    Commented Apr 10, 2015 at 14:35

Because this site is for professional sysadmins and without it we're inundated with "can you do my job for me" requests by people who aren't professional sysadmins.

Also because an essential part of being a professional sysadmin is having the skills to learn the basics on your own.

  • I wouldn't describe VPNs as 'the basics'. Increasingly common, yes, and once one has a secure understanding of levels, routing and all that jazz (which of course I have), not to hard to understand. But I wouldn't class them as basic (but each to their own). Commented Jun 24, 2014 at 13:10
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    @NormanGray I wouldn't even consider hiring a SysAdmin who didn't know how to setup at least one kind of VPN. They are well within "the basic", heck PPTP VPNs were covered in one of my college classes. Also, when in doubt, animal books.
    – Chris S
    Commented Jun 24, 2014 at 13:32
  • Well... perhaps you're right about 'basic'. My experience of the animal books is that they're better than the average, but still tend to provide too much detail (which goes out of date), and which in any case is better learned from manpages. Commented Jun 24, 2014 at 14:06

It also says in the close reason:

learning material recommendations are off-topic because they tend to become obsolete quickly

... and they do.

There's more than just that, like the fact that we're not librarians, here to tell people what books to read, but does "why" really matter? Requests for learning materials are off-topic, and knowing all the reasons why we've decided not to allow these types of questions won't change that.

  • But the two most useful resources I found (quoted in the question) date from 2006 and 2009: that's 'becoming obsolete' on a rather slower timescale than most answers on serverfault. In any case, it's clear that suggesting a change would be pointless, so I'm simply interested in the why. Commented Jun 24, 2014 at 13:18

It's worth noting that I and most people I know do not buy books on things that are part of ops, since they tend to become obsolete even as they are printed. This would include books on iptables, books on apache, and things like that.

This, even when we do buy books like the Intel ISA manuals, cryptography texts, and texts about programming languages. Those ones don't become obsolete.

Certainly, collections of links to tutorials become obsolete rapidly as sites change to a more "friendly" URL structure, rename themselves, or go away. Web indices and portals are out of favour for this exact reason.

In particular, questions asking for the best resource of some particular category are foul, since they are also opinion based.

Most of all, though, you should be able to find any online learning material in a couple minutes' searching in your favourite search engine, especially in this field. JFGI!

If you're hunting general book recommendations to help improve your career, asking in chat is a good thing to do - we appreciate the kind of character who would bother to read a book about systems admin in there, and usually give out book recommendations (with auto-expanding references to amazon) excitedly when asked. The reason is that chat is ephemeral, but Q&A is designed to be less so.


Amazon: 846 results for "VPN book"

That leaves way too many options and too much opinion on what constitutes a good book. What may be good for one may not be for another. This may be better left to the reviews on a book website such as Amazon or Barnes and Noble as opposed to a technical "forum" regarding this type of thing.

  • 2
    The problem with paper books is that they're typically padded with detail which, because it concerns specific products, dates quickly. And a lot of computing books are particularly bad for thinking that 'more pages' == 'better', hence more trees than wood. There's not a lot to understand about VPNs, but the core set of ideas interrelate slightly intricately, and that's what it's hard to find out about. Commented Jun 24, 2014 at 13:15
  • You asked for "compact overview of VPNs" then asked for "what is the structure of the VPN space" then your thought out loud with "where does IPsec fit into this jigsaw, I ask myself, or L2TP? Where does authentication fit in?". You are asking questions that could only possibly be answered by a book written specifically for VPN. The detail and breadth of the answers would be much too large for this medium. You have books strictly dedicated to IPSec and VPN. L2TP and VPN.
    – Travis
    Commented Jun 24, 2014 at 13:25
  • But if I want to read about IPsec or L2TP in a little more detail, I'd start with RFCs 4301 and 3931, and references therein. It's the framework into which they fit that's hard to find, because most information online (including on serverfault) is about specific problems with specific products. And the question wasn't for an explanation here, but for a pointer to known-good overviews elsewhere ("this made it clear to me"). In fact the OpenBSD document (as usual) was about right, though a little concerned with detail, and reassured me I'd already got the landscape about right. Commented Jun 24, 2014 at 13:38

The quick answer is that it is an easy way to cut down the number of questions which have to be answered and may otherwise be subjective.


There are lots of learning questions on SO because the idea of SO was to become the default place to search for programming questions. However that changed fairly rapidly and now those questions are mostly off topic (although the old answers are still there - search for what is a variable for examples) SF was originally aligned that was but quickly became a more exclusive site.

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