Yesware seems like a pretty neat tool… lots of my friends are in love with it!  It’s also always nice seeing a Boston-based company raising oodles of cash and rapidly expanding.

But, one problem: I really don’t want my friends to know exactly when - and where - I read their email.  It’s sorta creepy, you know?  Especially given the lack of transparency, as most people never know they are being tracked.

It’s kinda awkward socially

I have no problem with newsletters and marketing campaigns - i.e., people I don’t know - tracking whether or not I opened their email, along with where I am. Whatever.  No skin off my back.  But it’s a bit awkward when a friend goes, “Dude! I saw you opened my email yesterday! When the hell are you going to respond?!  And what were you doing in New York?!”  

I skim inbound emails frequently, but if I actually took the time to respond to each and every one in a timely manner, I’d never get any work done.  I like to maintain the polite fiction that I just might not have read your email until the end of the night… or maybe the next day.  

How it Works

Yesware uses standard tracking technology used by email newsletters.  When your friend uses Yesware to track whether you opened your email, a transparent one pixel image hosted at yesware.com is embedded in the body.  When it’s opened, presto - Yesware knows you opened it, along with your IP address (and therefore approximate location).

How to Block it

The easy way is to have your email client disable images.  But I like having images load automatically!  Privacy and pretty images shouldn’t be too much to ask for.

Thankfully, I - for some reason - still use Microsoft Exchange.  So I wrote a server-side rule to search all inbound emails for any images that link to “yesware.com”, and flag them.  I then wrote a client-side rule in mail.app to automatically delete these flagged emails, and reply with an email asking them to resend it without the tracking.

It’s not exactly foolproof.  But it works well enough for me, for now.

Thoughts on the Future

To be clear, I don’t blame Yesware.  They are creating a tool meant for salespeople, that’s been taken a bit beyond the intended use case.  If you are a Yesware subscriber, it’s easiest to just set up gmail to track every email you send.

But I do think they are playing with fire.  Right now, no one cares. It’s only a problem for me because I have a bunch of weird startup friends who spend most of their day writing emails to people asking for stuff.

But as services like Yesware become mainstream, there will be a backlash. My recommendation to Yesware?  Get ahead of the curve, and spend a couple of hours developing an opt-out list. 

If that existed, I would have simply added myself, and forgot about it.  Instead I’m writing a blog post, and sending out lots of “your email has been automatically deleted because you use Yesware” emails.