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I have been archiving emails for almost 17 years, and Outlook 2007 cannot handle the 3.2 gigabytes of emails. I want to achieve some tasks, listed below. I know software can do these things but the software I know about cost hundreds or thousands of dollars.

Tasks I would like to achieve

(many of the following ideas are from a blog post I made)

  1. Find and delete duplicate emails. I currently use Outlook Duplicate Items Remover by Vaita. It is good software and I recommend it. It only looks for duplicates within a folder, however, so if I have a duplicate in a different folder, it is undetected.
  2. Resort all emails into folders based on conversation. All emails from a person and sent to that person would be in the same folder. This is in opposition to all sent mail being in the Sent folder.
  3. Google mail has a beautiful way of representing email threads. Instead of forcing the user to read all of the extraneous quoted material, Google, elegantly hides the previous emails in a collapsible section. This exact feature is not easily replicated in Outlook, but I know it possible to clean out the massive amount of duplicate quoted material because there is software that does this. In lawsuits, for example, email is a major source of discovery material, and there are many companies that will re-thread email chains and remove the duplicate information in a thread--for a high price.

Some details

  1. I am happy to use multiple software add-ons if necessary.
  2. If I were not absurdly poor, I would happily pay for software. For now, I need free.
  3. I use PGP/GPG.
  4. I am willing to switch clients but the new client must support my existing PGP keys and cleanly import from Outlook 2007.
  5. My OS is Windows 7.

Thank you in advance.

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If it wasn't for cost I would recommend Outlook 2010/2013 as they have the conversational view built-in, with ClearContext for filing. This would of course support PGP and you would still be able to use your PST files.

To achieve this free, I can only see you achieving it by switching clients.

  1. The Client: Mozilla Thunderbird - Thunderbird is a free email application that's easy to set up and customize - and it's loaded with great features!

  2. The PGP keys: Thunderbird has an plugin called Enigmail - OpenPGP message encryption and authentication for Thunderbird and SeaMonkey.

  3. The Conversational View: Thunderbird Conversations - This plugin provides a conversation view for Thunderbird, grouping messages together and allowing you to reply "inline" thus providing a more efficient workflow.

  4. There are many plugins that remove duplicate messages - here are 2

    a. Remove Duplicate Messages - If you have duplicate messages (e.g. from merging folders or downloading messages several times) you can use this tool to find and remove them from the selected folder and its subfolder by rightclicking on a folder and choosing "Remove duplicates..."

    b. Remove Duplicate Messages (Alternate) - Search and remove messages which are the same as other messages in your mail folders (referred to as duplicates or dupes).

  5. I will refer to filing tools for this one as to me this sounds like you need an efficient filing system (I recommend - for Outlook - ClearContext - use this a lot)

    a. QuickFileMail - QuickFileMail is a Thunderbird Add-On that helps to quickly file messages in the right folder.

    b.Send and File - Allows to file outgoing messages in folder you prefer

    c. Outlook (and therefore possibly Thunderbird) gives you the option to either save sent messages in the sent mail folder, or in the same folder as the email you replied to.

As I'm a new user, I cannot post more than one link. So only the link to Thunderbird is there. If you want the rest, please comment below, and I will add the links in the comments. All these plugins are available from the Thunderbird plugins website.

I cannot testify for these plugins, these are based on research. I have used Thunderbird + Conversations, but none of the rest.

  • I had no idea that Outlook had improved that much in the latest editions, and I certainly had no idea Thunderbird was a viable client. I will certainly look into your recommendations! – hunterhogan Jan 17 '15 at 8:58
  • @HunterHogan out of interest - what path did you choose? Outlook or Thunderbird? – CalvT Jan 26 '15 at 15:59
  • Neither. Ha! If I had time, I likely would have switched to Thunderbird, but my already stranger-than-fiction life is in the process of becoming even more strange: I will soon be living, indefinitely, in a tent, hiking, without internet. So all of my computer time has been focused on transferring 200 GB of 17 years of data to the cloud. I wish I were kidding. What I just wrote is so unbelievable, that I literally (really, literally) re-read what I wrote because I thought, "There must be a mistake here." At least my life is never boring! – hunterhogan Jan 26 '15 at 21:00
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    @HunterHogan well I wish you luck!! I hope its a good tent... :D – CalvT Jan 27 '15 at 13:41

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