There is a bit of antiquated rules, but yeah most of them have their reasons. The whole point behind it amateur radio is to promote technology and communications, as well as provide an emergency backbone and fallback that the government doesn't have to fund, or really upkeep (since most of ham radio relies on self regulation and reporting).
Allowing encrypted comms would essentially destroy one of the primary tenets of amateur radio, inter-operability without massive coordination.
Now this doesn't mean you can't have security over the air. Just not really privacy. Nothing states you can't use modern crypto to generate signing keys and sign your message (not exactly feasible for voice, but digital yes) using asymmetric keys and common message authentication techniques.
There's some modern digital modes and messaging systems developing, but the lack of privacy and sometimes the nature of the common demographic within ham radio (non-pc savvy users, oddly) prevent the growth on new tech.
One reason much of radio is antiquated and old-fashioned is that the old technology is dead simple and just works. With a piece of wire and a simple radio, you can communicate regionally or globally without network infrastructure or mains power.
Still, it's really frustrating that we have to pay intermediaries for their centralized infrastructure in order to have general-purpose private conversations, even though we have the technology to do it on a peer-to-peer basis.
I understand private traffic isn't in the spirit of amateur radio, but it's frustrating that the only alternative is to go through the oligopoly of cell-phone networks.
I still have "cyberpunk" dreams of wide area mesh networks between peers, owned by no one, available to anyone who can cobble together the right equipment. Obviously we'd need some limitations to keep people from stomping on each other's traffic, but surely there's a middle ground.
I know you said you understand the reasoning, but for those who don't...
On the surface, prohibiting encryption seems antiquated and annoying, but if it weren't there would be no way to enforce the other regulations, like prohibiting transmissions for commercial purposes, which I think most hams would agree is a good restriction.
That said, if you really wanted to you could encrypt data and hide it using steganography or stuff it in what you claim is an authentication signature or something. It would be illegal but entirely unenforceable.
I could see allowing encryption, at least for the higher class licenses (extra + general?), as long as you are still required to identify your callsign unencrypted.
I also think the restriction on commercial purposes could be loosely interpreted to allow loading webpages with ads or buying something on an ecommerce site, as long as the primary purpose of the transmissions aren't commercial. But again, that would be difficult to enforce if encryption were allowed.
Higher class licenses open up more experimental spectrum usage. Inventing your own communication protocol/mode will give you some privacy, insofar as getting your message above the lowest-hanging fruit of other digital transmissions.
Technically 97.113(a)(5) takes care of commercial use where if you can use another service (aircraft radio, maritime radio, broadcast, CB, land mobile, whatever) then you're required to use it, and not use ham radio. Its to maintain the hobby-ness of ham radio.
WRT to your "administrative purposes" 97.219(d)(1) not only permits HTTPS and SSH, but requires it, in order to authenticate, presumably so unidentified or unauthorized people can't reconfigure your transmitter on top of the local air traffic control or something. Under 97.309(b) as long as you don't obscure the meaning you're all good. Obviously accessing administrative URLs is not an obscure meaning. Likewise tunneling a VPN trying to mimic administrative traffic to do illegal file downloading or something would be obscuring meaning.
I was surprised to hear this -- my understanding was that encryption was illegal in all cases (at least in the US). A quick googling found this, which sheds a good bit of light on the matter: http://www.amateurradio.com/encryption-is-already-legal-its-...
Agreed. It's infeasible to (legally) connect this type of system to the internet, at least in the US. FCC Part 97 also prohibits commercial transmissions, which would conceivably include advertisements, so you couldn't use this page to view any web page that contains ads. There goes most of the internet.
That said, I don't think this was ever intended to connect directly to the internet in this manner.
"...snip... Calls to place an order for a commercial product may be made such as the proverbial call to the pizza restaurant to order food, but not calls to one's office to receive or to leave business messages since communications on behalf of ones employer are not permitted..."
http://www.arrl.org/phone-patch-guidelines
Then I might try it. If done at the right time, it might kick off a two hour ragchew about health problems associated with elderly people and unhealthy food.
As I see it, living in the past is the charm of amateur radio. When radio communication was still somewhat exotic, it was new and cool to, if you set everything up just right, be able to communicate over large distances. Now, it's _old_ and cool to be able to do it with those primitive means.
I got my callsign a few years ago but never use it because of this. I wanted to use it more, but it felt like it was not a conductive place to research without supervision.
It's a shame, because radio is really interesting, but a lot (yes, not all) of amateur stuff feels as though it's stuck in the past.
Before I get lectured, yes, I understand most of the reasoning. That doesn't mean I have to like it.