http://arstechnica.com/security/2013/12/dear-gmailer-i-know-what-you-read-last-summer-and-last-night-and-today/
Dear Gmailer: I know what you read last summer (and last night and today)

 The widespread takeaway from today's announcement that Google will start
caching all remotely hosted images sent to Gmail
users<http://arstechnica.com/information-technology/2013/12/gmail-blows-up-e-mail-marketing-by-caching-all-images-on-google-servers/>was
that the move will hinder e-mail marketers and other nosy senders by
preventing them from seeing recipients' personal information. But less
reported was this: the move also promises marketers—and, indeed, other
types of shady senders—a major silver lining.

That's because of two ways Google has gone about implementing the change.
First, Gmail will begin displaying Web-based images by default, reversing
the years-long practice of automatically hiding them unless a user clicks a
button. And second, according to preliminary tests, the Google server that
temporarily stores the image contacts the Web address where the image is
hosted only after a user opens the message. And sometimes Google servers
request the image *each time* the message is opened. That means for the
first time in years, Gmail by default will allow senders who embed a unique
image address in each message they send to know which ones are ignored,
which ones are opened, and how many times they are viewed.

Rapid7 Chief Research Officer HD Moore sent several Gmail messages that
contained Web-based images hosted on servers he controlled. Then he
monitored the URLs of the images to see what happened. Each time, Google
servers didn't download the images until after he opened the Gmail message
and viewed the remote content. As Google promised Thursday
morning<http://gmailblog.blogspot.com/2013/12/images-now-showing.html>,
the new cached delivery system is safer and more secure, mainly because Web
requests to view remote images are no longer made by the end-user computer.
Having Google servers make the request instead prevents the image host from
being able to see the receiver's IP address, browser version, or other
system information.

This is mostly a terrific improvement and a good example of how Google
frequently outperforms its competitors in offering security improvements
such as always-on HTTPS Web encryption, SSL certificate pinning, and
two-factor authentication. Unfortunately, Google made another move on
Thursday that largely blunts those good works. By default, Gmail will no
longer hide remote images. That means that unless users make changes to
their default settings, it will be possible for senders to confirm whether
a message sent to a Gmail address has been opened.

It's simple for senders to do this. Embed in each message a viewable
image—or if you're feeling sneaky, a nearly invisible image—that contains a
long, random-looking string in the URL that's unique to each receiver or
e-mail. When Google proxy servers request the image, the sender knows the
user or message corresponding to the unique URL is active or has been
viewed. In Moore's tests, the proxy servers requested the image each
subsequent time the Gmail message was opened, at least when he cleared the
temporary Internet cache of his browser. That behavior could allow
marketers—or possibly lawyers, stalkers, or other senders with questionable
motives—to glean details many receivers would prefer to keep to themselves.
For instance, a sender could track how often or at what times a Gmail user
opened a particular message.

E-mail marketer Mail Chimp posted a blog
post<http://blog.mailchimp.com/how-gmails-image-caching-affects-open-tracking/>that
supported Moore's findings. Google
support 
pages<https://support.google.com/mail/answer/145919?p=display_images&rd=1>also
warn: "senders may be able to know whether an individual has opened a
message with unique image links." Unfortunately, the significant caveat is
missing from the blog post Google published Thursday.

Of course, Gmail users can easily prevent these details from being exposed
by reversing the change Google is in the process of rolling out. But given
the small percentage of people who change default settings for any software
or service, it's a fair bet that most Gmail users won't bother. So kudos to
Gmail for rolling out a safer way to deliver remote images, but let's not
give too much credit. The way the new system works now, it also gives a
major leg up to marketers and other senders many users would prefer to keep
in the dark.




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