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My employer requires that I encrypt a significant portion of my email in Outlook (we are currently using Outlook 2007). I would like to be able to search the contents of these emails, but there doesn’t seem to be a good way to do it:

  • Outlook’s internal search feature only searches the Subject line and senders/recipients of encrypted emails (it searches the bodies of unencrypted emails, though.) This happens for both the standard search and Advanced Search (CTRL+SHIFT+F)
  • Windows Search only searches the Subject line and senders/recipients of the encrypted emails (again, it searches the bodies of unencrypted emails)
  • Google Desktop Search 5.9...well, you get the idea.
  • Lookeen...same.
  • I attempted to install Lookout (as described in the post linked by aking1012), but I get an error message on startup "Sorry!! It looks like another Outlook Plugin has installed an unofficial version of the Outlook libraries which breaks Lookout. Lookout will not be able to load. For more information, see this link: http://www.lookoutsoft.com/Forums/topic.asp?TOPIC_ID=10". Even when I disable all add-ins (Tools -> Trust Center -> Add-ins), I get this error message.

I may be wrong, but I seem to remember that I had been able to index encrypted emails in an earlier version of Google Desktop. However, the current version does not appear to offer this capability.

Has anyone found a way to do this? Am I correct in remembering that Google Desktop used to do this? If so, what version?

UPDATE: Added results and clarifications based on aking1012's answer.

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if you could do it with google indexing, it would kind of defeat the purpose of the encryption –  hbdgaf Dec 2 '10 at 22:44
    
I realize that, but there are additional safeguards on my work machine that would make it difficult for an attacker to access any index that would be created. I would just like to be able to search the dozens of emails I get each day that are unnecessarily encrypted (at least in my view) –  Vector Dec 7 '10 at 13:22
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2 Answers

it looks like advanced search might do it: "The same search required me to open Advanced Search in Outlook (otherwise it searches subject lines only)". If you don't feel like clicking advanced you could try out the plugin they reference: http://www.userdriven.org/blog/lookout-search-plug-in-for-outlook.html

the article is from 2007 so it might be on the right version of outlook

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up vote 1 down vote accepted

WARNING: This is likely in violation of your corporate IT policy. Do this at your own risk.

Google Desktop 4 appears to index any encrypted emails that you have opened. The latest version (5.9) only appears to index encrypted emails that you create. To me, the older functionality is desirable.

I found links to many old versions at http://www.filehippo.com/download_google_desktop/1055/. The first version 4 there has worked well for me. I don't really have time to find out the version at which the functionality changed (my educated guess is at the first version 5 release).

Unfortunately, Google Desktop updates itself automatically, so unless you stop the update, you'll have the new version next time you boot the machine. There are probably several ways to prevent this, but the first one I found was to disable Google Update:

  1. Disable your network before you install Google Desktop
  2. Install Google Desktop
  3. Kill any GoogleUpdate.exe processes in the Task Manager
  4. Start 'msconfig'
  5. Go to the 'startup' tab and uncheck "Google Update"
  6. Reboot
  7. Reenable your network on boot.

You may want to check msconfig periodically to make sure Google Update doesn't start again; installing other Google software (like Earth, Chrome, or Picasa) may reenable it.

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