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SimplyFile Add-on for MS Outlook

If you are a Microsoft Outlook user and you have dozens and dozens of folders to help keep your inbox clean and your emails organized you know that moving those emails to the appropriate folder can be quite the task, especially if you have nested folders. SimplyFile from TechHit can help by “learning” your folder structure and suggesting the correct folder to store an email or a batch of emails. There are additional features, like creating email folders from a spreadsheet and filing sent messages (no more BCCing yourself). The product is not flawless, but it can certainly help you keep your inbox manageable.

About SimplyFile

SimplyFile is an Outlook add-on that only runs in the installed desktop version of Microsoft Outlook, and works with Outlook 2010, 2013, 2016, 2019, Office Microsoft 365 (64 and 32 bit). It does not work with web-versions of Outlook or Outlook Express. If you are using IMAP from Gmail in Outlook it is likely to be too buggy to be useful. Individual users can download the latest version (v5) because it does not require admin rights, through there is an all-user install that an administrator can push out to all Outlook users in the firm.

The cost of SimplyFile v5 starts at $2.99 a user/month billed annually for Standard and goes up to $7.99 user/month for the Ultimate version. SimplyFile Pro, at $60 annually ($4.99 user/month), is the best package for most users, if features like “find related messages” and bulk creation of folders are important. If you have an older version of SimplyFile you get discount upgrade pricing, which may be worth the cost because of new features like “Undo Send”.

Getting Started

When you install SimplyFile a new group will appear in the Home tab of the Outlook ribbon. Click on “More” and “Train Simply File”. It scans through your folders and teaches the AI which emails will likely go into which folder. It identifies potential folders for messages based on keywords, subject, senders, and more. Depending on how many folders and how many emails you have this “training” may take a while, and you will not be able to use Outlook while it goes through this process.

Once you have the add-on installed and trained you can customize the SimplyFile group in the Ribbon. Click on “More” and “Options”. In the UI tab, you can check boxes to display certain functions in the Ribbon. The SimplyFile group can take up a good bit of space on the Ribbon, so you can pick and choose what to show.  For instance, check the box for “One-Click File” and “Show 2 one-click-file buttons” and you can see SimplyFile’s best guess for appropriate folders for selected emails. Check the box for “Quick Pick” so if none of the suggestions are right you can just type in the folder name. All the functions are always available under “More” and “All Actions”. Once you have used the product for a while you will know which functions you want displayed.

In the Options dialog box click on “Filing” to control behaviors for sent messages and when it files a message. For instance, uncheck “Mark messages as read” when filing a message. There is an experimental feature that lets you add a category when you file a message. These are not Outlook categories, but the promise of automating categories when you file a message is worth keeping an eye on for further enhancements.

SimplyFile has extensive documentation on their website. Here are all the settings and what they mean in the Options menu.

Basic Uses

Select any email message in your inbox and look at the SimplyFile group in the Ribbon to see options for the best folder for that message based on the AI in SimplyFile. Click on the folder in SimplyFile and the email is automatically moved. No dragging and dropping (and risking dragging an email into the wrong folder!). If you open an email you can also see suggested folders in the SimplyFile ribbon. Click the folder and the email is whisked away. If the suggested folders are not correct click “Quick Pick” and type the name of the folder to move the email to any folder you have in Outlook. You can also create a new folder from the Quick Pick menu, file the email and go to the folder (File and Go), and under “More Actions” discover options like “File the Last Message in this Thread and Delete the Rest” or “File and Print”.

Need to clean up your inbox in a hurry? You can file by thread (subject) or by sender and make quick work of moving lots of emails into the appropriate folders. Or try the Batch File command, which will go through your inbox and suggest folders before moving messages. One of the comforting aspects of SimplyFile is that unlike many other add-ons that attempt to help you triage your inbox, SimplyFile gives you the final decision on how to act. In the Batch File command you can skip flagged messages and unread messages, thus leaving an inbox of emails that needs some action. Need to clean up your inbox and just keep the last message by thread or sender? The Cleanup button will do just that.

Powerful Options for Sent Mail

One of the powerful features in SimplyFile revolves around sending messages. If you are sending a new message you will notice after you install the add-on that your options for sending the email have expanded, and a new SimplyFile group will appear in the Ribbon. You can send the message and save it in the Sent folder as is the default in MS Outlook. Or, you can choose to Send & File. If you choose that option, then before the message is sent you can choose which folder the email should be saved in. No need to BCC or CC yourself so you can move your sent messages to the client folder. In Options go to the Filing tab and check the box for “When filing a sent message, leave a copy in the Sent Items”.

When you reply to an email, if you choose the “Send & File” button in the SimplyFile ribbon, a dialog box will appear with many options. One of the most useful is “Send, File and File Original”.  As suggested, this function will file the message you are replying to (the original) and your sent message in the folder of your choice, save a copy in your Sent folder and send the message. That way you can folder the sent message and the message in your inbox in one fell swoop.

Many More Features to Explore

There are many other features to explore, like “Reply with Attachment”, “Undo Send”, Snooze It, and bulk creation of folders across the firm. Visit the extensive documentation in the User Guide on the TechHit website to learn more about how to take advantage of SimplyFile. TechHit also makes many other Outlook add-ons that lawyers may find useful, like SendAware to confirm recipients before you send an email and MessageSave for Outlook email archive and backup.


While the SimplyFile add-on will only help you when you are using the installed MS Outlook, it is still quite useful for helping keep your emails organized and in the correct folders. Microsoft has many features that SimplyFile either leverages or duplicates like tasks (TaskIt), scheduling (ScheduleIt) and search (Find), but the easy identification of the right folders and the additional filtering options for sent mail may be worth the cost in helping manage your inbox.