Am I being paranoid about emails?
May 25, 2010 9:49 AM   Subscribe

Am I being paranoid about Outlook email, Microsoft and privacy?

I'm using Outlook 2007. Occasionally recently I've created a message, hit "Send/Receive", and seen the pop-up say "Sending 2 messages". When I check my Sent Mail box, there's only the one that I had planned to send. I thought maybe I hadn't checked properly and had maybe had an unsent message waiting in the Outbox, so I just frowned let it ride. But today I was suspicious and went through the whole procedure very carefully. There's no doubt it told me I was sending 2 messages, but I really only sent one that I'm aware of.

Not that this happens every time - only now and then, which is why I don't have any empirical data to provide for analysis. But I'm wondering if I've inadvertently used some trigger-word recently (like NSA or Menwith Hill) which is causing somebody somewhere to want to look more closely at my mail.

I've posted this question to a very helpful and reliable Windows-specific BBS which has always helped me resolve problems in the past, but I'm getting soothing, reassuring "me too" replies which are not reassuring me. Not the other posters' fault, of course: it's me being paranoid. Isn't it? Please say it's just me...

What's going on here? Is Microsoft sending information about me that I'm not authorising? If so, where? And what? Any ideas?
posted by aqsakal to Computers & Internet (9 answers total) 1 user marked this as a favorite
 
I don't know how your Outlook is configured, but if you want to see what kind of network connections are being established from your computer, you can use a network sniffing tool like WireShark. In the simplest mode, it should show you the servers you computer is connecting to. If you want to go deeper, you can look at the contents of the packets, though this may not be that useful if you're going over an encrypted connection.
posted by chengjih at 10:04 AM on May 25, 2010


Best answer: According to an Outlook MVP in this thread, it's just a bug:
It means you're seeing a bug in Outlook 2007 that causes it to say that it's sending more messages than it really sends. It's not actually sending two messages, but x + y messages, where "x" is the number of messages it actually is sending and "y" is one less than the number of accounts you have defined. I don't know if Microsoft is aware of this problem and I don't know when it will be fixed.
posted by bcwinters at 10:07 AM on May 25, 2010


Best answer: It's you being paranoid. If Microsoft was doing something this obviously, it would be everywhere on the internet and no business anywhere would use Outlook.
posted by inigo2 at 10:20 AM on May 25, 2010


Best answer: In the vanishingly unlikely event that the security services are monitoring your e-mails, you're not going to find evidence of it on your computer. Just sayin'!
posted by jaffacakerhubarb at 10:26 AM on May 25, 2010


Response by poster: Well yes, those replies are pretty reassuring. But I'll still keep tabs on it instead of hitting "Send/Receive" and going for a coffee.

In fact, I have 3 accounts defined (although one of them is the Hotmail Outlook Connector thingie), so x+y = 1+(3-1) = 3, so sending 1 email would show "Sending 3" (or "Sending 2" if the Hotmail thingie isn't counted). But, as I said, it's not every time, just sometimes.

Thanks for helpful replies.
posted by aqsakal at 11:27 AM on May 25, 2010


Use a program like CCleaner to delete temporary files, and see if it happens after that.
I have had similar problems that this has solved.
posted by weapons-grade pandemonium at 2:13 PM on May 25, 2010


Like they say, if you hear hoofbeats in Central Park, think "horses" not "zebras." In this case, NSA spying is definitely a zebra.

(The NSA wouldn't need to trick your Outlook into sending 2 copies of your email, anyway. They'd either sniff your connection and read your email as it was sent, or commandeer your external mail server and get copies there. That's why they went to all the trouble to build Echelon.)

In this case, the first obvious "horse" is the thing about the pop-up dialog being wrong. I can believe that.

But if you want to skip that and take extra steps, I'd say the next "horse" is malware. I can easily envision a program that sits in Outlook and sends one spam message every time you authenticate to send an outgoing real message.

(Of course, a program clever enough to delete sent copies of itself would probably be clever enough to trick Outlook into NOT saying "sending 2 messages." But whatevs.)

Update your antivirus, scan the crap out of your computer, install all Windows patches, etc.
posted by ErikaB at 3:12 PM on May 25, 2010


Best answer: Could also be return-receipts going out.
posted by gjc at 4:37 PM on May 25, 2010


Response by poster: Thanks, w-gp - yes, I use CCleaner every time I shut down (using the run and shutdown option). Even created a desktop item just for that purpose. Thanks, ErikaB - yes, daily updated antivirus, fully patched, at least one monthly total scan and intermediate ones when I see something suspicious (like this). And your horses and zebras metaphor really convinced me. Thanks, gic - I hadn't thought of that. Seems quite likely now that you point it out.

So I'm still paranoid, but I'll point it somewhere else now.
posted by aqsakal at 11:28 PM on May 25, 2010


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