A while back, I blogged about trust on the web, and how there are a lot of assumptions made by content providers that simply don't carry over to end users, or are just a small (but important) step from being good practices.

Yesterday, at $work, we were talking about something that lead to a discussion on SSL, and how I think that most sites, even if they don't contain sensitive information should be available by https—even if the certificate is self-signed.

Chris respectfully (I think (-; ) disagreed with me saying that certificates that are not trusted a user's browser are as bad, or even worse than not allowing SSL at all. His theory—and I'm sure he'll correct me if I'm misrepresenting him—is that offering this type of unverifiable certificate is not only useless, but harmful to users because there's a false sense of security. My retort, though not well received, is that users of modern browsers (Firefox at least) will be notified when a self-signed certificate that they've accepted has changed. This at least allows the user to verify when something is amiss. His rebuttal was that there's no way for the user to tell which certificate is the "good" one, and which is the "bad" one, and I can see his point.

We had a discussion on DNS and how we trust it for a lot of things that we shouldn't, even though we don't want to... especially given the recent problems with DNS. In the end, we all agreed that putting something like http://omniti.com/ on self-signed https serves no practical value as users will a) never use it, b) not know how to verify the certificate, and c) will get confused by their browser warning them about security problems.

This lead to a few other branches of thinking about SSL. The first was a question Chris asked us "how do access your online banking?" clarifying with "how do you get to the login page?" A few of us (myself included) answered "bookmark" while others said they hit their bank's main domain either from URL history or manually, and clicked through from there. Chris's point was that most users visit http://bank.example.com/ and are somehow directed their https login page. I checked my bank, and bad things happen:

• visit http://www.royalbank.ca/
• click "online banking", which links to http://www.rbcroyalbank.com/STRINGHERE/redirect-bank-hp-pagelink-olb.html
• which redirects, via META tag to: https://www1.royalbank.com/cgi-bin/rbaccess/RESTOFURLHERE
• user is presented the login form (in https)

My bookmark is the https://www1.royalbank.com/... page, so I feel relatively safe, but let's look at the bad things that happen here:

• User visits one domain (HTTP, not secure)
• User is _silently_ redirected to another domain on HTTPs

Why are these bad? Well, aside from the possible confusion of getting bumped from royalbank.ca to rbcroyalbank.com to royalbank.com, the user's chain of trust breaks down when they visit http://royalbank.ca/. http—no "s". If this site was compromised, the user would never know (without careful URL confirmation at the https destination) that s/he was not maliciously redirected to https://www1.roya1bank.com/ (note "L" is "1" (one) in my bad-guy example). Phishers could easily get a SSL certificate for roya1bank.com.

That got me thinking a bit about the SSL certificate acquisition process. I'm sure some of the really high-end SSL certificates still come with human validation (a real person looks at the application and makes a real decision about granting the certificate; in the case above, hopefully this would have been caught). Most certificate signing I've seen recently is based on proven ownership of the domain in question. So, as I say, it's trivial for me to go register a domain that LOOKS like a bank. Sure, I'd still have to compromise either the http server or DNS that points at the server, but Kaminsky demonstrated that this isn't so hard (or wasn't until just a few weeks ago).

Let's take it a step further back. If bad guys can compromise DNS, which is inherently insecure (not SSL, no trust model other than IP address, and it runs on UDP(!)), then surely they can trick your the certificate authority's SMTP server to deliver mail to another mail exchanger, right?

• bad guy targets example.com poisons the certificate authority's DNS for example.com to point MX at an IP controlled by bad guy
• bad guy generates a certificate signing request (CSR) and send it to the certificate authority (CA), "From" bob@exmaple.com
• CA receives the CSR and verifies with whois that the contact for the domain is bob@example.com
• CA signes the CSR and returns the certificate to bob@example.com (either by mail or through a web interface)
• bad guy is now in posession of a perfectly valid and trusted http://example.com/ SSL certificate

Scary. You must be thinking that CAs probably have a more secure DNS setup and wouldn't get poisoned (as easily). I believe that to be somewhat true. Let's say it's absolutely true: the CA has 100% perfectly secure DNS. Ok, we'll need to go one step further back:

• bad guy poisons the DNS for the target's less secure $20/month ISP, example.com, to redirect the MX for example.com to a different server
• bad guy visits example.com's registrar's web interface and indicates that he has forgotten his password
• registrar generates password reset URL/instructions and emails it to bob@example.com
• bad guy receives the hijacked email, logs into the domain and changes the contacts to badguy@example.net, an email account that he controls
• bad guy generates a CSR and sends it to the CA from badguy@example.net, and continues the process outlined above to receive a legitimate, valid and trusted certificate

In any of these scenarios, hundreds or thousands of account credentials could be acquired—especially with creative use of proxies at the bad guy's malicious server.

We're lead to believe that SSL is truly safe, and it's true that the encryption part lives up to the expectation, but modern practice of the certificate generation/signing process certainly leaves something to be desired, I think.

Yeah, it might be a long shot that an attacker could easily poison specific DNS servers on the internet, but again, as Kaminsky showed the world just a few weeks ago, (nearly?) every DNS server on the planet was vulnerable to exactly this type of attack before summer 2008.

Pardon me if I don the tinfoil hat until we all forget about this mess.