Five Years Too Late

September 19, 2008

Eric’s Email Misadventure

Filed under: General, Uncategorized — Tags: , , , , , , — fiveyearstoolate @ 9:08 am

We love hosted software models. You can call it SaaS. You can call it cloud. You can even still call it ASP if you’re old-school like that. Scalable. One code base.  Subscription revenue. Users can’t screw it up and incur a bunch of support costs. All good.

But a few weeks back the potential downside of these services showed up in an unpleasant way, right in my inbox. All of a sudden I just wasn’t getting very much email. This isn’t ego – the volume of mail was suspiciously low, especially given how many emails I had sent out the previous week, having recently returned from vacation. There was nothing obviously wrong. Emails weren’t bouncing and if you sent an an email called “test” it arrived no problem. The IT guys sent me emails in from all kinds of crazy domains to see if I had an overactive spam filter. Mail from Russian ISPs arrived unmolested. “No problem” they declared.

Problem was I’d had several people tell me they’d sent me emails that I didn’t receive (including a company that showed up at our offices having confirmed a meeting via an email I never got). So they looked. And looked. They deleted my profile on the exchange server and reinstated it. They were about to blow up the whole exchange server and start over when they figured it out.

When I got back from vacation I had put in place a new signature for my emails, one which featured the URL for my tumblelog, It had not occurred to me (or to anyone) that this would be any kind of issue, but when the IT guys started pulling apart an email we knew failed through repeated testing, it was in fact my signature causing the problem. Specifically, the string “”.

Any email that contained that string failed to deliver to my inbox. Apparently (we later learned) a hosted security product used by our (hosted) disaster recovery product had somehow flagged poor tumblr as dangerous, and was simply killing any emails containing the domain. No quarantine, no spam filter. These were killed long before they ever got to our server.

All’s well that ends well, of course. I changed my sig (although I’m sure many people are deprived for the lack of my scintillating content) and sent out a big mea culpa to anyone I’d emailed in the affected week (since it was all replies with my quoted signature that got blasted) and we moved along.

But it certainly highlights a slight lack of control and transparency that comes with outsourcing (for lack of a better word) one’s software. Convenient and easy to administer? Absolutely. But imperfect in ways I hadn’t necessarily focused on prior to this misadventure.

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  1. SaaS models are the most efficient and lucrative way to sell software. Licensing arrangements are a thing of the past (extremely sensitive applications like finance and legal may be the exceptions). I can’t tell you the last time we saw a company present to us a licensing model, and those that had it in the past are transitioning to SaaS. led the revolution. The upshot is that SaaS is no longer a differentiator for software providers.

    Comment by Andres Moran — September 19, 2008 @ 9:45 am

  2. And I’m glad your email is working again. I remember I was one of your testers. 🙂

    Comment by Andres Moran — September 19, 2008 @ 9:47 am

  3. Andres – don’t mistake this anecdote as a condemnation of SaaS. Far from it – we are as much in favor of the model as you. But this illustrated that while SaaS reduces complexity in some very meaningful and value-adding ways, it also obscures some operations in ways that aren’t immediately visible. And also, there is some evidence that SaaS businesses take longer to build to profitability and to a large scale. There was an interesting Deutsche Bank Report on this last year.

    Comment by fiveyearstoolate — September 19, 2008 @ 9:54 am

  4. I know you weren’t condemning SaaS. You were clear and accurate on your praise of its merits. I just decided to add a tangential point on its ubiquity. And yes, it does take longer to build to large scale. I will look for that Deutsche report if its available online.

    Comment by Andres Moran — September 19, 2008 @ 10:13 am

  5. While outsourcing can be a source of the problem in this case it’s really more a lack of transparency. Whenever Information Security is separated from operational IT, a lack of change management and clear communication can significantly impact any enterprise. The “service” or “application” of security is oftentimes at odds with the use of informational “technology” on many levels and deciding how to trade off safety of content with freedom of access will decide the success of failure of many organizations.

    Comment by Mizer — September 20, 2008 @ 3:39 pm

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