SimplyFile for MS Outlook

There are many MS Outlook add-ons that mimic functionality that is already built into the application. Though Techhit’s SimplyFile would seem to fall into that category since MS Outlook has a strong rules function and has added the “Move” group in the Home tab, it is actually amazingly useful despite some overlap. SimplyFile is an “intelligent filing assistant for Microsoft Outlook” and costs $50US. So, is it worth it?

Files, folders and rules are the boon and curse of the MS Outlook organizational structure. Why? Lawyers use folders and subfolders to keep client and matter correspondence filtered from the rest of their inboxes. Even though folders are one way to get email out of the inbox, the extra step to drag and drop an email to a folder often doesn’t get done. Rules in MS Outlook can help, but they can’t anticipate every new situation, and no one wants to be creating, editing, and deleting rules all the time. Wouldn’t it be nice to have Outlook anticipate and suggest which folder an email should be filed in, and make it happen with a single click? That is what SimplyFile does.

Installation and Configuration

I tested the add-on with MS Outlook 2010 with a local MS Exchange server. Under the system requirements on the Techhit website they note known issues with Google Apps Sync and Outlook 2010 using Gmail via IMAP. Also it not supported on Mac OS X. There is a 30 day free trial so you can test it before you purchase to make sure it works with your system and configuration. If you meet the requirements then installation should be quick and seamless. From the website screenshots I would suggest that the user interface in Outlook 2010 is by far the most pleasing and functional.

After installation it is worth taking a short time to read the online Quick Start Guide. Without it you likely wouldn’t know that first thing you must do is “train” the add-on by letting it learn your folder structure. There are other tips and tricks in the manual, but if you are impatient you need read no further than how to train it and you’ll be on your way.

Filing Incoming Email

Once SimplyFile is trained you are ready to go. Highlight a message in your inbox and SimplyFile suggests what folder to file it in. One click and you are finished. Likewise in an open email look in the toolbar to file it in one click. The “Move” group in MS Outlook tries to anticipate which folder you would like to use as well, though I am not sure what the logic behind it is because it often doesn’t suggest a likely candidate from my 140 (and growing) folders. SimplyFile does. And, the more you use the add-on the better it gets. If SimplyFile misses the mark on the suggested folder of course there are several options for the user to pick a folder by search or by a sorted list. (Figure 1)

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One feature SimplyFile provides that is not available natively in MS Outlook is the ability to move an open email to the calendar or tasks. Yes, you can create a QuickStep to do this (and I have), but SimplyFile builds this in. In addition to folders, SimplyFile gives you the option to “task it” or “schedule it” for open and closed emails (Figure 2). My only issue with the “schedule it” feature is that it sets up the email as a new meeting with the recipients in the “to” line. If you just want to add the email to your calendar as an appointment you can delete the email addresses in the “to” line and click the “save” icon instead of the “send” button. Or, set up a QuickStep appointment button to fill that need.

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SimplyFile also lets you file by message threads or by message sender. Or, if you are ready to clean up your inbox all at once, (assuming you have most of the folders you need) try the “batch file” function. This feature runs the SimpleFile engine on your inbox and suggests which folder it thinks each email should be moved to. Uncheck the box if you disagree with its logic – you will still have a much cleaner inbox at the end of the process (Figure 3).

Figure 3

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Filing Outgoing Email

Ok, great, but what about organizing sent mail? I know many lawyers bcc themselves on outgoing messages, sometimes to confirm that it was sent but often to make it easier to file the correspondence in the proper folder. For lawyers who struggle with organizing sent messages SimplyFile’s sent message features pays for the product in time savings.

Any time you click to send an email in MS Outlook a popup appears with a series of options: Move to selected folder and send; Send, file and file original; Send and save in sent items; Send without saving a copy; Send the message, file it and add it to your tasks or calendar; Send, file and print. You can disable this functionality entirely if you are content to save all outbound emails in your sent folder (Figure 4).

Figure 4

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I believe that the SimplyFile add-on for MS Outlook 2010 provides an intuitive and easy way to move emails to folders for organizational purposes. The accurate folder suggestions, one-click filing, and the sent message organization fill a need not already available in MS Outlook. It is both a time saver and helps manage client correspondence. To me, it is worth the money.


  1. Catherine – thank you very much for such a detailed review!

    By the way, you can change “Schedule It” to create appointments instead of meetings (without inviting message recipients) by unchecking “ScheduleIt – Invite Message Recipients to the Meeting” on the Actions tab of the Options window –

    Thank you again!

  2. I concur that this program is a must-have. I formed my own law practice in January and had the advantage of building my systems and assembling my programs from scratch. I investigated the options for mail organization and found Simply-File to be the best. It has been extremely helpful for me, especially as I am a paperless office and have a heavy email load. I have over 250 folders to date and create a new one for each client I receive. With Simply-File, I do not have to worry about misfiled communications (among other perks).

    Great program – glad you reviewed.

  3. I heard about simplyfile from another CPA. I installed the free trial version and knew I would pay for the full version by the end of the day. I keep a folder for each client and I LOVE being able to file my sent and my received items in the same folder. If/When you determine that a folder is no longer needed you can use Tech Hit’s MessageSave program to save emails into a folder and thus reduce the size of your PST file.

    Awesome program!