Eliot Lear's Ramblings

People in my company travel a lot, and they like to have their itineraries easily accessible.  My wife wants to know when and where I will be, and that’s not at all unreasonable.  So, how best to process and share that information?  There are now several services that attempt to help you manage it.  One of those services, TripIt.Com, will take an email message as input, organize your itinerary, generate appropriate calendar events, and share that information with those you authorize.

The service is based in the U.S., and might actually share information with those you do not authorize, to market something to you- or worse.  If the information is stolen, as was the case with travel information from a hotel we discussed recently, it can be resold to burglars who know when you’re way.  That can be particularly nasty if in fact only you are away, and the rest of your family is not.

But before we panic and refuse to let any of this information out, one should ask just how secure that information is.  As it happens, travel itineraries are some of the least secure pieces of information you can possibly have.  All a thief really needs is an old ticket stub that has one’s frequent flyer number, and we’re off to the races.  In one case, it was shown that with this information a thief could even book a ticket for someone else.

So how, then, do we evaluate the risk of using a service like TripIt? First of all, TripIt does not use any form of encryption or certificate trust chain to verify their identity.  That means that all of your itinerary details go over the network in the clear.  But as it turns out, you’ve probably already transmitted all of your details in the clear to them by sending the itinerary in email.  Having had a quick look at their mail servers, they do not in fact verify their server identities through the use of STARTTLS, not that you as a user can easily determine this in advance.

Some people might have stopped now, but others have more tolerance for risk.

Perhaps a bigger problem with TripIt is that neither its password change page nor its login page make use of SSL.  That means that when enter your your password, the text of that password goes over the network in the clear, for all to see.  It also means that you cannot be sure that the server on the other end is actually that of TripIt.  To me this is a remarkable oversight.

For all of these concerns, you still get the ability to generate an iCal calendar subscription as well as the ability to share all of this information with friends and family.  Is it worth it?  One answer is that it depends on whether you actually want to enter the information yourself, whether you care about security concerns, and whether you like using calendaring clients.  It also depends on what other services are available.

Another service that is available is Dopplr.  It also attempts to be a social networking site, not unlike Linked In.  Dopplr allows you to share you itineraries with other people, tells you about their upcoming trips (if they’re sharing with you), and it lets you create an iCal subscription.

Dopplr also has some security problems, in that they do not use SSL to protect your password.  They also do not use SSL for their main pages.  They do, however, support OpenId, an attempt to do away with site passwords entirely.  I’ll say more about OpenId in the future, but for now I’ll state simply that just because something is new does not make it better.  It may be better or worse.

And so there you have it.  Two services, both with very similar offerings, and both with almost the same privacy risks.  One of them, by the way, could distinguish themselves by improving their privacy offering.  That would certainly win more of my business.