Journal tags: tls

Back in March, I wrote about a dilemma I was facing. I could make the certificates on The Session more secure. But if I did that, people using older Android and iOS devices could no longer access the site:

As a site owner, I can either make security my top priority, which means you’ll no longer be able to access my site. Or I can provide you access, which makes my site less secure for everyone.

In the end, I decided in favour of access. But now this issue has risen from the dead. And this time, it doesn’t matter what I think.

Let’s Encrypt are changing the way their certificates work and once again, it’s people with older devices who are going to suffer:

Most notably, this includes versions of Android prior to 7.1.1. That means those older versions of Android will no longer trust certificates issued by Let’s Encrypt.

This makes me sad. It’s another instance of people being forced to buy new devices. Last time ‘round, my dilemma was choosing between security and access. This time, access isn’t an option. It’s a choice between security and the environment (assuming that people are even in a position to get new devices—not an assumption I’m willing to make).

But this time it’s out of my hands. Let’s Encrypt certificates will stop working on older devices and a whole lotta websites are suddenly going to be inaccessible.

I could look at using a different certificate authority, one I’d have to pay for. It feels a bit galling to have to go back to the scammy world of paying for security—something that Let’s Encrypt has taught us should quite rightly be free. But accessing a website should also be free. It shouldn’t come with the price tag of getting a new device.

Universal access is at the heart of the World Wide Web. It’s also something I value when I’m building anything on the web. Whatever I’m building, I want you to be able to visit using whatever browser or device that you choose.

Just to be clear, that doesn’t mean that you’re going to have the same experience in an old browser as you are in the latest version of Firefox or Chrome. Far from it. Not only is that not feasible, I don’t believe it’s desirable either. But if you’re using an old browser, while you might not get to enjoy the newest CSS or JavaScript, you should still be able to access a website.

Applying the principle of progressive enhancement makes this emminently doable. As long as I build in a layered way, everyone gets access to the barebones HTML, even if they can’t experience newer features. Crucially, as long as I’m doing some feature detection, those newer features don’t harm older browsers.

But there’s one area where maintaining backward compatibility might well have an adverse effect on modern browsers: security.

I don’t just mean whether or not you’re serving sites over HTTPS. Even if you’re using TLS—Transport Layer Security—not all security is created equal.

Take a look at Mozilla’s very handy SSL Configuration Generator. You get to choose from three options:

1. Modern. Services with clients that support TLS 1.3 and don’t need backward compatibility.
2. Intermediate. General-purpose servers with a variety of clients, recommended for almost all systems.
3. Old. Compatible with a number of very old clients, and should be used only as a last resort.

Because I value universal access, I should really go for the “old” setting. That ensures my site is accessible all the way back to Android 2.3 and Safari 1. But if I do that, I will be supporting TLS 1.0. That’s not good. My site is potentially vulnerable.

Alright then, I’ll go for “intermediate”—that’s the recommended level anyway. Now I’m no longer providing TLS 1.0 support. But that means some older browsers can no longer access my site.

This is exactly the situation I found myself in with The Session. I had a score of A+ from SSL Labs. I was feeling downright smug. Then I got emails from actual users. One had picked up an old Samsung tablet second hand. Another was using an older version of Safari. Neither could access the site.

Sure enough, if you cut off TLS 1.0, you cut off Safari below version six.

Alright, then. Can’t they just upgrade? Well …no. Apple has tied Safari to OS X. If you can’t upgrade your operating system, you can’t upgrade your browser. So if you’re using OS X Mountain Lion, you’re stuck with an insecure version of Safari.

Fortunately, you can use a different browser. It’s possible to install, say, Firefox 37 which supports TLS 1.2.

On desktop, that is. If you’re using an older iPhone or iPad and you can’t upgrade to a recent version of iOS, you’re screwed.

This isn’t an edge case. This is exactly the kind of usage that iPads excel at: you got the device a few years back just to do some web browsing and not much else. It still seems to work fine, and you have no incentive to buy a brand new iPad. And nor should you have to.

In that situation, you’re stuck using an insecure browser.

As a site owner, I can either make security my top priority, which means you’ll no longer be able to access my site. Or I can provide you access, which makes my site less secure for everyone. (That’s what I’ve done on The Session and now my score is capped at B.)

What I can’t do is tell you to install a different browser, because you literally can’t. Sure, technically you can install something called Firefox from the App Store, or you can install something called Chrome. But neither have anything to do with their desktop counterparts. They’re differently skinned versions of Safari.

Apple refuses to allow browsers with any other rendering engine to be installed. Their reasoning?

Security.

In the latest issue of Justin’s excellent Responsive Web Design weekly newsletter, he includes a segment called “The Snippet Show”:

This is what tells all our browsers on all our devices to set the viewport to be the same width of the current device, and to also set the initial scale to 1 (not scaled at all). This essentially allows us to have responsive design consistently.

<meta name="viewport" content="width=device-width, initial-scale=1">

The viewport value for the meta element was invented by Apple when the iPhone was released. Back then, it was a safe bet that most websites were wider than the iPhone’s 320 pixel wide display—most of them were 960 pixels wide …because reasons. So mobile Safari would automatically shrink those sites down to fit within the display. If you wanted to over-ride that behaviour, you had to use the meta viewport gubbins that they made up.

That was nine years ago. These days, if you’re building a responsive website, you still need to include that meta element.

That seems like a shame to me. I’m not suggesting that the default behaviour should switch to assuming a fluid layout, but maybe the browser could just figure it out. After all, the CSS will already be parsed by the time the HTML is rendering. Perhaps a quick test for the presence of a crawlbar could be used to trigger the shrinking behaviour. No crawlbar, no shrinking.

Maybe someday the assumption behind the current behaviour could be flipped—assume a website is responsive unless the author explicitly requests the shrinking behaviour. I’d like to think that could happen soon, but I suspect that a depressingly large number of sites are still fixed-width (I don’t even want to know—don’t tell me).

There are other browser default behaviours that might someday change. Right now, if I type example.com into a browser, it will first attempt to contact http://example.com rather than https://example.com. That means the example.com server has to do a redirect, costing the user valuable time.

You can mitigate this by putting your site on the HSTS preload list but wouldn’t it be nice if browsers first checked for HTTPS instead of HTTP? I don’t think that will happen anytime soon, but someday …someday.

I’ve been updating my book sites over to HTTPS:

• domscripting.com
• bulletproofajax.com
• html5forwebdesigners.com

They’re all hosted on the same (virtual) box as adactio.com—Ubuntu 14.04 running Apache 2.4.7 on Digital Ocean. If you’ve got a similar configuration, this might be useful for you.

First off, I’m using Let’s Encrypt. Except I’m not. It’s called Certbot now (I’m not entirely sure why).

I installed the Let’s Encertbot client with this incantation (which, like everything else here, will need root-level access so if none of these work, retry using sudo in front of the commands):

wget https://dl.eff.org/certbot-auto
chmod a+x certbot-auto

Seems like a good idea to put that certbot-auto thingy into a directory like /etc:

mv certbot-auto /etc

Rather than have Certbot generate conf files for me, I’m just going to have it generate the certificates. Here’s how I’d generate a certificate for yourdomain.com:

/etc/certbot-auto --apache certonly -d yourdomain.com

The first time you do this, it’ll need to fetch a bunch of dependencies and it’ll ask you for an email address for future reference (should anything ever go screwy). For subsequent domains, the process will be much quicker.

The result of this will be a bunch of generated certificates that live here:

• /etc/letsencrypt/live/yourdomain.com/cert.pem
• /etc/letsencrypt/live/yourdomain.com/chain.pem
• /etc/letsencrypt/live/yourdomain.com/privkey.pem
• /etc/letsencrypt/live/yourdomain.com/fullchain.pem

Now you’ll need to configure your Apache gubbins. Head on over to…

cd /etc/apache2/sites-available

If you only have one domain on your server, you can just edit default.ssl.conf. I prefer to have separate conf files for each domain.

Time to fire up an incomprehensible text editor.

nano yourdomain.com.conf

There’s a great SSL Configuration Generator from Mozilla to help you figure out what to put in this file. Following the suggested configuration for my server (assuming I want maximum backward-compatibility), here’s what I put in.

Make sure you update the /path/to/yourdomain.com part—you probably want a directory somewhere in /var/www or wherever your website’s files are sitting.

To exit the infernal text editor, hit ctrl and o, press enter in response to the prompt, and then hit ctrl and x.

If the yourdomain.com.conf didn’t previously exist, you’ll need to enable the configuration by running:

a2ensite yourdomain.com

Time to restart Apache. Fingers crossed…

service apache2 restart

If that worked, you should be able to go to https://yourdomain.com and see a lovely shiny padlock in the address bar.

Assuming that worked, everything is awesome! …for 90 days. After that, your certificates will expire and you’ll be left with a broken website.

Not to worry. You can update your certificates at any time. Test for yourself by doing a dry run:

/etc/certbot-auto renew --dry-run

You should see a message saying:

Processing /etc/letsencrypt/renewal/yourdomain.com.conf

And then, after a while:

** DRY RUN: simulating 'certbot renew' close to cert expiry
** (The test certificates below have not been saved.)
Congratulations, all renewals succeeded.

You could set yourself a calendar reminder to do the renewal (without the --dry-run bit) every few months. Or you could tell your server’s computer to do it by using a cron job. It’s not nearly as rude as it sounds.

You can fire up and edit your list of cron tasks with this command:

crontab -e

This tells the machine to run the renewal task at quarter past six every evening and log any results:

15 18 * * * /etc/certbot-auto renew --quiet >> /var/log/certbot-renew.log

(Don’t worry: it won’t actually generate new certificates unless the current ones are getting close to expiration.) Leave the cronrab editor by doing the ctrl o, enter, ctrl x dance.

Hopefully, there’s nothing more for you to do. I say “hopefully” because I won’t know for sure myself for another 90 days, at which point I’ll find out whether anything’s on fire.

If you have other domains you want to secure, repeat the process by running:

/etc/certbot-auto --apache certonly -d yourotherdomain.com

And then creating/editing /etc/apache2/sites-available/yourotherdomain.com.conf accordingly.

I found these useful when I was going through this process:

• Certbot documentation
• How to secure your Apache using Certbot SSL
• Mozilla SSL Configuration Generator
• SSL Server Test

That last one is good if you like the warm glow of accomplishment that comes with getting a good grade:

• domscripting.com
• bulletproofajax.com
• html5forwebdesigners.com

For extra credit, you can run your site through securityheaders.io to harden your headers. Again, not as rude as it sounds.

You know, I probably should have said this at the start of this post, but I should clarify that any advice I’ve given here should be taken with a huge pinch of salt—I have little to no idea what I’m doing. I’m not responsible for any flame-bursting-into that may occur. It’s probably a good idea to back everything up before even starting to do this.

Yeah, I definitely should’ve mentioned that at the start.

Mozilla—like Google before them—have announced their plans for deprecating HTTP in favour of HTTPS. I’m all in favour of moving to HTTPS. I’ve done it myself here on adactio.com, on thesession.org, and on huffduffer.com. I have some concerns about the potential linkrot involved in the move to TLS everywhere—as outlined by Tim Berners-Lee—but still, anything that makes the work of GCHQ and the NSA more difficult is alright by me.

But I have a big, big problem with Mozilla’s plan to “encourage” the move to HTTPS:

Gradually phasing out access to browser features.

Requiring HTTPS for certain browser features makes total sense, given the security implications. Service Workers, for example, are quite correctly only available over HTTPS. Any API that has access to a device sensor—or that could be used for fingerprinting in any way—should only be available over HTTPS. In retrospect, Geolocation should have been HTTPS-only from the beginning.

But to deny access to APIs where there are no security concerns, where it is merely a stick to beat people with …that’s just wrong.

This is for everyone. Not just those smart enough to figure out how to add HTTPS to their site. And yes, I know, the theory is that is that it’s going to get easier and easier, but so far the steps towards making HTTPS easier are just vapourware. That makes Mozilla’s plan look like something drafted by underwear gnomes.

The issue here is timing. Let’s make HTTPS easy first. Then we can start to talk about ways of encouraging adoption. Hopefully we can figure out a way that doesn’t require Mozilla or Google as gatekeepers.

Sven Slootweg outlines the problems with Mozilla’s forced SSL. I highly recommend reading Yoav’s post on deprecating HTTP too. Ben Klemens has written about HTTPS: the end of an era …that era being the one in which anyone could make a website without having to ask permission from an app store, a certificate authority, or a browser manufacturer.

On the other hand, Eric Mill wrote We’re Deprecating HTTP And It’s Going To Be Okay. It makes for an extremely infuriating read because it outlines all the ways in which HTTPS is a good thing (all of which I agree with) without once addressing the issue at hand—a browser that deliberately cripples its feature set for political reasons.

Tim Berners-Lee is quite rightly worried about linkrot:

The disappearance of web material and the rotting of links is itself a major problem.

He brings up an interesting point that I hadn’t fully considered: as more and more sites migrate from HTTP to HTTPS (A Good Thing), and the W3C encourages this move, isn’t there a danger of creating even more linkrot?

…perhaps doing more damage to the web than any other change in its history.

I think that may be a bit overstated. As many others point out, almost all sites making the switch are conscientious about maintaining redirects with a 301 status code.

(There’s also a similar 308 status code that I hadn’t come across, but after a bit of investigating, that looks to be a bit of mess.)

Anyway, the discussion does bring up some interesting points. Transport Layer Security is something that’s handled between the browser and the server—does it really need to be visible in the protocol portion of the URL? Or is that visibility a positive attribute that makes it clear that the URL is “good”?

And as more sites move to HTTPS, should browsers change their default behaviour? Right now, typing “example.com” into a browser’s address bar will cause it to automatically expand to http://example.com …shouldn’t browsers look for https://example.com first?

All good food for thought.

There’s a Google Doc out there with some advice for migrating to HTTPS. Unfortunately, the trickiest part—getting and installing certificates—is currently an owl-drawing tutorial, but hopefully it will get expanded.

If you’re looking for even more reasons why enabling TLS for your site is a good idea, look no further than the latest shenanigans from ISPs in the UK (we lost the battle for net neutrality in this country some time ago).

BT just inserted a popup into someone’s site, encouraging me to switch on content filtering. That is Very Not Cool. pic.twitter.com/QMnLRawsNW

— David Thompson (@fatbusinessman) December 30, 2014

They can’t do that to pages served over HTTPS.

Throughout the Brighton Digital Festival, Lighthouse Arts will be exhibiting a project from Julian Oliver and Danja Vasiliev called Newstweek. If you’re in town for dConstruct—and you should be—you ought to stop by and check it out.

It’s a mischievous little hardware hack intended for use in places with public WiFi. If you’ve got a Newstweek device, you can alter the content of web pages like, say, BBC News. Cheeky!

There’s one catch though. Newstweek works on http:// domains, not https://. This is exactly the scenario that Jake has been talking about:

SSL is also useful to ensure the data you’re receiving hasn’t been tampered with. It’s not just for user->server stuff

eg, when you visit http://www.theguardian.com/uk , you don’t really know it hasn’t been modified to tell a different story

There’s another good reason for switching to TLS. It would make life harder for GCHQ and the NSA—not impossible, but harder. It’s not a panacea, but it would help make our collectively-held network more secure, as per RFC 7258 from the Internet Engineering Task Force:

Pervasive monitoring is a technical attack that should be mitigated in the design of IETF protocols, where possible.

I’m all for using https:// instead of http:// but there’s a problem. It’s bloody difficult!

If you’re a sysadmin type that lives in the command line, then it’s probably not difficult at all. But for the rest of us mere mortals who just want to publish something on the web, it’s intimidatingly daunting.

Tim Bray says:

It’ll cost you <$100/yr plus a half-hour of server reconfiguration. I don’t see any excuse not to.

…but then, he also thought that anyone who can’t make a syndication feed that’s well-formed XML is an incompetent fool (whereas I ended up creating an entire service to save people from having to make RSS feeds by hand).

Google are now making SSL a ranking factor in their search results, which is their prerogative. If it results in worse search results, other search engines are available. But I don’t think it will have significant impact. Jake again:

if two pages have equal ranking except one is served securely, which do you think should appear first in results?

Ashe Dryden disagrees:

Google will be promoting SSL sites above those without, effectively doing the exact same thing we’re upset about the lack of net neutrality.

I don’t think that’s quite fair: if Google were an ISP slowing down http:// requests, that would be extremely worrying, but tweaking its already-opaque search algorithm isn’t quite the same.

Mind you, I do like this suggestion:

I think if Google is going to penalize you for not having SSL they should become a CA and issue free certs.

I’m more concerned by the discussions at Chrome and Mozilla about flagging up http:// connections as unsafe. While the approach is technically correct, I fear it could have the opposite of its intended effect. With so many sites still served over http://, users would be bombarded with constant messages of unsafe connections. Before long they would develop security blindness in much the same way that we’ve all developed banner-ad blindness.

My main issue—apart from the fact that I personally don’t have the necessary smarts to enable TLS—is related to what Ashe is concerned about:

Businesses and individuals who both know about and can afford to have SSL in place will be ranked above those who don’t/can’t.

I strongly believe that anyone should be able to publish on the web. That’s one of the reasons why I don’t share my fellow developers’ zeal for moving everything to JavaScript; I want anybody—not just programmers—to be able to share what they know. Hence my preference for simpler declarative languages like HTML and CSS (and my belief that they should remain simple and learnable).

It’s already too damn complex to register a domain and host a website. Adding one more roadblock isn’t going to help that situation. Just ask Drew and Rachel what it’s like trying to just make sure that their customers have a version of PHP from this decade.

I want a secure web. I’d really like the web to be https:// only. But until we get there, I really don’t like the thought of the web being divided into the haves and have-nots.

Still…

There is an enormous opportunity here, as John pointed out on a recent episode of The Web Ahead. Getting TLS set up is a pain point for a lot of people, not just me. Where there’s pain, there’s an opportunity to provide a service that removes the pain. Services like Squarespace are already taking the pain out of setting up a website. I’d like to see somebody provide a TLS valet service.

(And before you rush to tell me about the super-easy SSL-setup tutorial you know about, please stop and think about whether it’s actually more like this.)

I’m looking forward to switching my website over to https:// but I’m not going to do it until the potential pain level drops.

For all of you budding entrepreneurs looking for the next big thing to “disrupt”, please consider making your money not from the gold rush itself, but from providing the shovels.