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Encrypting Emails (not w/Priv.ly)

May 1, 2012

I apologize in advance – this blog is supposed to be focused on privacy on social media with Priv.ly, but perhaps it should expand a bit…  If you are interested only in Priv.ly – feel free to skip this one, or you may wnat to read, you may find it interesting anyway.

Today I had a customer request that I use encrypted emails for sending them confidential information.   This seemed like a reasonable request and given my interest in supporting privacy I thought this would be a great opportunity to practice what I preach.  I work for a large computer company and we have a large generally very good IT support staff, so I thought this would be easy…

Wow, what a pain in the neck.

First, I had to create a digital cerificate.  This was cool – I expected to need to do this.   I went ahead and did it – in my default browser – Firefox.  I then spent an hour or so trying to get Outlook 2007 to import / use the certificate I created, with no luck.  I gave up doing it myself and called our support organization.  They were as usual very helpful, but this was evidently not a typical request for them.  They finally figured out that on WinXP, the only supported way to create the certificate and get it into Outlook is to use IE 6 or IE7.  Care to guess what version I’m running – Yup you got it. I run IE 8 on the work laptop.

So the support person had to uninstall IE 8, install the certificate with IE6,  then reinstall IE8.  Then we started in Outlook to try it out.  At first it seemed to work.  I was able to send a digitally signed email to the customer, then an encrypted one and I thought we were OK.  Then I started asking questions about how do I know it is encrypted.  It really isn’t so obvious.

Of course, the initial certificate I created was already sent to the customer, so I have gotten some occasional emails from him that I can’t open – since they were encrypted to the wrong key.

It’s working now, and with Outlook, after setup,  isn’t too hard to do on a regular basis.  All my emails to/from this customer are now encrypted.

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