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Security Expert: Yahoo's Email Encryption Needs Work 123

itwbennett writes "On Tuesday, Yahoo delivered on a promise that it made in October to enable email encryption for everyone by default by January 8. While this is a great step, the company's HTTPS implementation appears to be inconsistent across servers and even technically insecure in some cases, according to Ivan Ristic, director of application security research at security firm Qualys. For example, some of Yahoo's HTTPS email servers use RC4 as the preferred cipher with most clients. 'RC4 is considered weak, which is why we advise that people either don't use it, or if they feel they must, use it as a last resort,' Ristic said."
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Security Expert: Yahoo's Email Encryption Needs Work

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  • Progress. (Score:5, Interesting)

    by ptudor ( 22537 ) on Thursday January 09, 2014 @03:53AM (#45904879) Homepage Journal

    It's important to remember that only a year ago RC4 was a recommended solution and TLS1.2 support in browsers like Firefox and older operating systems has been slow to arrive. So I look at this as an important first step, with progressive refinements sure to follow. In the same way that Facebook introduced https in response to Tunisia and slowly made it an option for all users before making it default, Yahoo, while slow in adopting a model of default security, has to walk similar steps. They may have had an SSL-beta-option for the last year, but given their AOL-Like user base, I can understand being conservative in adopting new methods and being liberal in the ciphers they provide. Someone using Chrome in Mavericks may expect support for SPDY3 with AES-GCM, but for a user base that may be using IE6 or FF3 on XP still, for a company that caters to people who will never know what GCM or SHA2 is it best to avoid the headline, "Yahoo Mail is Broken for tens of thousands of users." They'll get there. Thanks for trying, Yahoo.

    Now, can someone at Microsoft turn on STARTTLS? For that matter, I wish NANOG would turn on STARTTLS for inbound connections.

    Also, IPv6... please... IPv6...

  • by korbulon ( 2792438 ) on Thursday January 09, 2014 @05:20AM (#45905081)

    Yahoo reminds me of a journeyman heavyweight boxer taking the champ into deep rounds despite taking a serious beating. He simply will not go down.

    They impress for sheer resilience, if for nothing else.

  • by VortexCortex ( 1117377 ) <VortexCortex AT ... trograde DOT com> on Thursday January 09, 2014 @08:11AM (#45905525)

    In order for me to thrive as a business I merely need to make enough money to pay expenses and employees. I don't have to defeat the heavyweight. I just have to dodge their blows.

    The stock market's demand for growth is untenable. Overextended businesses die; The name for unchecked growth is cancer. I've discovered that business maturity exists. Focusing on improving my services and better ability to meet customer needs / better dialog beats overextension through growth hands down. On the public market I'd be slaughtered. I refuse to grow faster than necessary. This way I can stay more nimble and adjust to changes and new tech faster than my competition. Instead of growing, I concentrated on streamlining agility. Eg: You could invent 50 new platforms tomorrow. In one year, I'll have support for them all without requiring any growth to gain the specialization. I have an excellent platform abstraction layer.

    I'm not partial to Yahoo, but their board has more sane business sense than most. Their retention isn't necessarily impressive, but to dodge blows while in dire need of a tourniquet is commendable. It's caused them to make some compromising business decisions, however.

  • by cffrost ( 885375 ) on Thursday January 09, 2014 @09:29AM (#45905849) Homepage

    So if a website gives you only HTTPS with RC4 or HTTP in clear text as options - why would you choose clear text?

    This is totally illogical. Yes RC4 sucks but it is better than clear text - ANYTHING is better than clear text. The only possible argument for this would be "false sense of security", but if you think average people pay any attention to that padlock in the status bar, you are delusional.

    I agree with you wholeheartedly — in fact, I accept some questionable certs in my zeal to transfer ciphertext instead of plaintext.

    However, I neglected to mention in my previous post that I also use EFF's "HTTPS Everywhere," [] and an extension for that extension called "HTTPS Finder" [] — the former forces HTTPS if the host is known to support it, and the latter forces HTTPS if an HTTPS connection is possible (and creates a new rule for "HTTPS Everywhere"), even with requisite security.ssl3. cipher suites disabled in about:config .

    (I figured anyone knuckle-deep in their browser's HTTPS configuration would be aware of them (and hopefully, using them). I recommend both, emphatically — "HTTPS Everywhere" alone yields a vast improvement in security/privacy, and has the benefit of a very long, expert-managed list of defaults.)

    Thus, if RC4 is needed and I have it disabled, I'll be presented with an "ssl_error_no_cypher_overlap" error page, then I enable RC4 and reload. The only weakness there is in my forgetting to re-disable RC4, but the two extensions I mentioned in my initial post help in this effort, alerting me in various ways if/when I connect to another host using weak security:

    "CipherFox" displays the cipher suite (or configurable portions thereof) in use on the status bar (e.g., it shows me "AES-256 RSA-4096 SHA1" on DDG), as well as providing the "Enable RC4" check-item on the Tools menu.

    "Calomel SSL Validation" displays (on my nav. bar) a color-coded shield that represents a percentage security rating based on weighted factors drawn from the cert and cipher suite, the breakdown of which is displayed via clicking the shield icon.

  • Re:Ya-what? (Score:5, Interesting)

    by TheloniousToady ( 3343045 ) on Thursday January 09, 2014 @09:43AM (#45905921)

    OK, I'll bite. There still are a few things they do well. For example, their Finance feature [] is among the best in class of financial information (IMHO).

    I began using their email system as a POP server years ago, mainly because I thought the spam filtering worked very well. At some point, they changed their system so that you had to use their address as the reply address, so I began using that rather than my website's forwarding address. Although that should have alienated me and made me go elsewhere, I stuck with them, so now people are used to replying to the Yahoo address and it's hard to switch to something else.

    I used to use their "classic" (old-fashioned) mail but they forced me and everyone else out of that last year. So, I got used to the new email interface and even generally like it now, but the performance problems still are inexcusable. For example, I sent one email several times the other day after their system said it had failed to send it, then multiple copies of it appeared in my "Sent" list. So, did it go out or not? - who knows?

    Their longstanding "Groups" system still has some attractive features. I tried to find a replacement for it recently for an email list I've run for several years, and I couldn't find any similar free and ready-made (no installation) email group service that allows users to subscribe themselves.

    There seems to be a theme lately of Yahoo changing the cosmetics of their system as often as possible. However, they don't seem to understand that users don't want change unless there is a clear benefit to them. And users also don't want continuous change - they need time to digest each new thing that's foisted on them. Yahoo also seems to be disregarding the impact all these changes have on system performance. Even after tolerating senseless change, I'm just about ready to abandon their email due to its increasingly poor performance.

    I find their search to be OK, though I'm not particularly loyal to it. Honestly, I can't tell much difference between Yahoo/Bing search and Google, so I just use whichever one comes up in the browser I happen to be using. However, my perception is that Google is very slightly better.

    Overall, the challenge for Yahoo is to modernize their systems after years of neglect, while retaining the things that people like about them (in my case: finance, spam filtering, and groups), without impacting quality in terms of performance and security. They might get to the Promised Land one day, but there's a lot of desert to cross first.

"I will make no bargains with terrorist hardware." -- Peter da Silva