July 13, 2020

Improving Retention Labels in Microsoft 365

6 minute read

In early 2018, Microsoft released Retention Labels for Office 365 (now Microsoft 365) to allow "labels" to be place on content in SharePoint, OneDrive, and Exchange.  Users with an E3/G3 license can manually use these labels to give the file or email a retention period in which the item will be automatically deleted.  Organizations with E5/G5 license, or the E5 Compliance add on can also automatically apply content to these same locations using keywords, metadata, or trainable classifiers.  At Gimmal we're huge fans of these new features in Microsoft 365, but we also found room for some needed improvements.

The first thing we noticed when trying to automatically apply labels was that the editor is not very intuitive.  This causes difficulty in building and managing the rules.  There is a lack of indication about what metadata is possible, what the syntax is, or how to reuse the queries for other labels.  Gimmal resolves this problem with reusable rules that can be easily created using our rule editor.

Hierarchical File Plan

Next, we realized that while the File Plan in Microsoft 365 had most of the elements records managers would want, it was not hierarchical, and it made it difficult to organize retentions schedules.  We resolved this by building the ability to create parent/child relationships between classifications while also making them easily work with labels from Microsoft 365.

Case Records

While basic records retention is often as simple as keeping items until they haven't been viewed or modified for a while, records management software needs to be able to start retention when an event happens.  Luckily, this is possible with Microsoft 365, however, the next thing that begins to happen is that tens, hundreds, and sometimes thousands of files end up being related to an event and are all part of one particular case.  Take personnel files, for example. There is only one event that typically expires these records, and that is the date the person was no longer an employee.  Without Gimmal, each file would be an individual record, needing individual approval for disposition.  With Gimmal software, records managers only need to manage the case rather than the individual files.

Gimmal also has the ability to automatically create new case records on the fly so there is no manual intervention required in creation.  To finalize how powerful our case records capabilities are, you can use Power Automate to generate events directly from your business applications.  For example, using an event from Workday to drive when an employee retention timer needs to start.


Often when using Microsoft 365 retention labels, the proof of concept is moving along nicely and may have even made it into production when someone realizes that the wrong label is getting applied to content.  No one seems to understand why some files have the wrong label, and they often never figure it out.  What has usually happened in this case is two-fold.  First is that unbeknownst to those setting up automatically applied policies is that two policies inadvertently have similar rules and the wrong one is winning.  The worse part about this is there is no way to change the prioritization of these labels.  Gimmal resolves this problem by allowing you to place a priority on each classification, and when combined with the ability to make the file plan hierarchical, it becomes a very powerful way to create a parent that can catch all files that don't fall into more granular classifications.

Retention Triggers

The key to meeting the retention rules associated with most organizations is complete flexibility on how retention will begin.  Gimmal adds the ability to create and reuse triggers to start the retention timer on Microsoft 365 content.  We also allow many types of triggers that are not available out of the box when using retention labels.

  • Custom date properties - Specifically for SharePoint, the ability to use custom dates as triggers
  • Rule based triggers - The ability to create a rule to determine when retention should start
  • Recurring events - Events that automatically occur on a schedule, such as monthly, quarterly, or annually

Parallel Retention Paths

What if the retention for a particular type of record isn't completely linear?  Maybe there are two possible paths depending on some other days.  Perhaps there are two different rules that need to be followed, and the destruction date will vary depending on when each trigger fires.

Gimmal handles this by enabling you to build lifecycles that can allow for multiple phases, with the possibility of some being parallel.  Like all elements of File Plan in Gimmal, these lifecycles are reusable to simplify the maintenance of your compliance system.


Retention Labels in Microsoft 365 are a great tool for helping organization do records management.  From trainable classifiers to easily applying to large quantities of files in places like OneDrive and Exchange, the functionality seems to be a welcome addition for many organizations.  We do believe though that moving beyond basic retention schedules, a highly flexible retention engine is needed and will ultimately save time and cost less over the long haul.

Learn how to boost your information governance program with Microsoft 365 and beyond HERE!


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