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TROUBLESHOOTING 101 for 365 | SHAREPOINT - ISSUES DELETING CONTENT

  • 10 hours ago
  • 11 min read

Author: Jonathan Stuckey


Audience: SharePoint consultant; M365 support engineer; Support content creator


Not the most frequent of issues, but problems with deleting a folder or document can be one of the most frustrating for users and support teams alike.


patch-panel cabling - blue cables
Its always the red-wire...

This article is a return to the series of SharePoint Online problem identification, diagnostics and resolution. It covers the possible source of the issue and the triage options to narrow down root-cause.


This topic assumes that, as reader, you are a power-user or administrator with the relevant knowledge and access to undertake the actions.


While you don't need to know all the in's and out's of the underlying platform, basic triage and understanding of the implications of each service you are interacting with is key to supporting organisations using SharePoint Online and Microsoft 365.


Problem statement

User attempts to remove a folder (or multiple nested folders) and the Delete command fails. This can be seen for a standard folder or a documentset in a library. The basic message dialogue pop-up indicating item cannot be deleted

e.g.

small message dialogue indicating failure to delete item in the SharePoint site library
Generic action failure message
note: this can also be seen in issues with bulk-delete of multiple documents

Starting point

With the basic structure of SharePoint your issue identification typically reduces at each step of root-cause analysis. Unfortunately, this isn't the case when you have deployed additional services such as:


  1. Microsoft Teams sites

  2. Microsoft Teams channel sites

  3. Microsoft Purview Retention policies

  4. Microsoft Purview Retention labels

  5. Microsoft Archive

  6. SharePoint Embedded (Containers)


What is normally a basic set of steps we can use to trace and issue to one of the following:

  • permissions and access rights

  • environmental or device issues

  • user training or behaviours


We now need to include:

  • tracing business process rules

  • external service configurations

  • service boundaries (or integration issues)


In the following sections we identify what and where you can get to the bottom of the problem.


Triage Issues with Deletion

The following represent the most common causes of issues with deleting SharePoint's library content, and specifically folders with documents. Typically, during a root-cause investigation you work your way down the steps until you find the specific contributing factors in your scenario, but key is understanding the context and your environment. First steps are always: What's different to normal, and is the behaviour being experienced actually a problem - or just a lack of understanding?


The very first questions whenever uncovering a problem is to ask...

  1. were you (ever) able to do this before? If so - when was the last time?

  2. should you be able to delete this item/structure?


Only if you get positive confirmation on the above, then there are a limited number of potential causes. The basic diagnostic checklist for root-cause analysis in this case is work your way down the checklist:


Triage Checks

1. Permissions Issues

Ranking: no1 cause of issues with deleting

Confirm you / the user has Delete permissions at both the library and folder level.


Action: Check for broken permission inheritance.

For detail breakdown on verifying permissions see TROUBLESHOOTING 101 for 365 | SHAREPOINT - CHECKING ITEM PERMISSIONS

Once have proven access permissions are correct, or resolved any issues with access, re-try Delete as user (and again as Site Administrator.)



2. Checked-Out or Locked Items

Ranking: no 2 most likely cause of tickets


Action: As site administrator / Owner check folder structure for checked-out items.

  • Go to Library

  • navigate to the point in the Library / folder structure

  • either

    • visually scan down files looking for items showing 'checked-out' icon,

      List of documents show in the SharePoint Documents library. A highlighted document draws attention to a red-icon with an angled down arrow - indicating items is Checked-out. A column to the right of the item, called 'Checked Out To' indicates the name of the person who checked-out the document.
    • or update current view and add the 'Checked Out To' column and save:

      A Library's view configuration screen, with the 'Checked Out To' column highlighted and selected - to be added to current view for users to see.
  • If can identify the item causing the issue, and who has checked-out the document

  • Contact person and request checked-in item, or over-ride check-out.

NOTE: As site Owner you can override the check-out and discard changes to roll-back to the previous version - but this will result in data-loss from minor version removal.

Supplemental action:

Some files may not show-up if your role is not SharePoint Administrator and the file(s) that are checked out or have no checked-in version in the folder(s). This can be further complicated if contents have broken inheritance and the user(s) do not have the rights to see the items.


Action: As site administrator / Owner check 'Manage files with no checked-in version' in Library settings.


  • Go to Library

  • navigate to the Library settings

  • Click 'manage files which have no checked-in version'

    Document settings page with options: List Info, General, Permissions, and Communications. "Manage files" highlighted in blue.
  • If files from location listed - check-item(s) box

  • Click 'take ownership of Selection'

  • Navigate back to the library

  • Locate the file you have taken ownership of (it is now checked-out to you)

  • Highlight file and either

    • check-in file if this needs to be kept, and relocated, or

    • delete the file to remove from folders


3. Other services preventing actions: Sync or Workflow Dependencies

Ranking: no 3 most likely cause of issue - with no tooling for discovery


Determine if the folder is linked to OneDrive sync or active workflows (Automate).


3.1 Using the Add shortcut to OneDrive (Sync)

You will have to do this the long-way round because Microsoft has neglected to retain the management features for this functionality when they moved to Connect to OneDrive, vs. SharePoint Sync. ..don't ask.


Action: Ask the user if they have the library connected to their OneDrive (or their peers do?)

Action: Resolve dependencies before re-attempting deletion.


Once you have identified user(s) syncing library, check for synchronisation of specific folder(s), and unlink the connections that maybe holding open the connection (and preventing deletion).


When all connections unlinked and folders are not connected in a OneDrive, attempt to delete.

Microsoft 365 Purview Audit Events log extensive tracking for file access and sync, but not for the creation or usage of OneDrive shortcuts by a user. Audit search does not show you required information.

3.2 Automate workflows tied to the library

Two levels of access in root-cause for checking Power Automate flows.


Those available via site/library in the UI and normal SP Admin roles:

SharePoint Library toolbar, with elipsis menu option open to - Automate - Flows - and indicating now flows active
Quick self-check of Automate Flows for any deployed

Action: Using site-collection admin or SharePoint admin check for Library-scoped flows (legacy)

  • In library, open the Automate menu

  • check Flows linked to the library.

  • if any exist, confirm the owners and disable temporarily to test if Delete starts working


And those that need elevated administrative level privileges:

The Manage tab operational dashboard in Power Platform Admin center. Indicates data on no. of Flows, Runs, Failures etc.
Power Platform administration center - view of Automate runs.

Action: As Power Platform Administrator role check login into admin and check run-health and suspended flows:

  • navigate to the Power Platform Admin Center

  • open Manage, set Environment to production (if you have more than one)

    • Select Power Automate tabe

    • Filter on environment

    • Check toggle for Failed Runs - validate against location of issue.

  • open Monitor the Environment

    • select Cloud flows and filter listed items by site/library

    • review recent runs, errors, retry storms, or long-running flows.


In event of stalled or failed Automate flow, you can try to re-start the flow. Sometimes this can down to:


  1. the credentials for the account that the trigger or connectors used by the automate have expired and need re-authenticating - this can be updated and resumed.


    Once the automate is working again, check if the Deletion is now working in the library.


  2. one (or more) of the triggers or connectors in the Automate flow are deprecated and the Flow needs to be updated with new/different connectors - this requires a re-write of the Automate Flow. This may mean that the Automate needs to be disabled and retracted while a resolution is put in place.


    Once disabled / removed, re-try the delete action in the library.


  3. the Automate has been hibernated by Microsoft, because was waiting longer than default period (6-months). The automate may need to be updated (or disabled / removed) before you can re-test for Delete function working as expected.


For other problems, you will need skills of a Power Platform developer to help in resolving the issue(s).

NOTE: Even if there isn’t a workflow visible in the library UI, flows elsewhere may be listening to the site/library via SharePoint triggers via Graph or webhooks.

4. Microsoft Teams Channel Folder

Ranking: Less likely cause, but seen more over last few years


Check if the user is trying to remove a Channel folder provisioned from Microsoft Teams. If user is trying to delete a level 1 folder in Shared Documents library, they may have got this confused with other folders created manually or by other users.


Action: check if site is connected to a Microsoft Team

You will know if the site is connected to Microsoft Teams icon visible on the sites banner:

Screen snipping showing sharepoint site banner of site. Shows icon area, Site name (Finance) and Microsoft Teams logo - in White on dark blue background

If the folder is tied to a Microsoft Teams channel, delete the channel first (assuming this is a legitimate action, and not a misunderstanding by end-user) - then retry the Delete / Move command.


5. Site Storage or System Errors

Ranking: Unlikely to occur unless you do not manage tenancy capacity properly, or Admin have missed (frequent) message-centre notifications.


Check if the site has exceeded its storage quota, as this can prevent basic functions for occurring as expected. Will prevent range of commands including: Add/Upload, Move (to site), Delete in the site...


Action: As SharePoint Administrator role check site allocation in SP Admin Centre

  • If at site-limit (or over) allocate more storage to tenancy or site

  • If no issues with tenancy storage, or site storage allocation, check for app integration or external connectors to your site


See 3rd party apps and integrations comments in the Wrap-up


Action: Look for background deletion processes or system errors.


See section 3.2 on Workflows, or potential for retention Policy or Label to block the action (see sections on Retention - 6, 7) or 3rd party integrations.


6. Retention Policies or Legal Holds

Ranking: Is an extremely likely cause if your organisation makes use of Purview Retention options without understanding appropriate usage.

Pre-requisite: elevated roles or access privileges are required for the following checks

Action: Check if the Site, Library, folder or its contents are under a retention policy. Raise a request, or if you have appropriate delegated privileges access:



Action. Check for if an eDiscovery or legal hold is in place on the site


In the event of an Open Case placing a hold on the site you are trying to delete content from, you will have to raise a request to either get site released from the case (and the Hold) or factor in the appropriate operational response while the case is ongoing.


Once an eDiscovery case is closed, the contents on the site will be released and all effective labels and processes will re-engage. i.e. All retention labels and policies which have reached Disposition will be enacted, PreservationHoldsLibrary content which has expired will be purged, and Recycle Bin (stage 2) items which are retained will be disposed and lock release on structure for deletion.


7. Retention Labels

Ranking: Is a likely possibility if your organisation has an Information or Records Mgmt function or has engage consultants to setup information lifecycle management.


Action: Check site Recycle bin for deleted items from location.

INFORMATION: remember that there are 2 recycle bins on site and second requires Site-collection admin role to access.

Action: Verify if any retention labels are applied to the folder or its contents.

Check for Retention Label attached to item or items in the folder


step-1 - check the properties of the items in the folder - it is always the last property at the bottom of the properties panel

view of a sharepoint library with call-outs highlighting the Retention  Label column and visible label attached to a document in the library
An IM view of content details helps quickly view Retention and Sensitivity labelling applied

step-2 - check the library settings [site settings > library settings > more settings > Apply label to items in this list or library] and confirm

if labels are available for the site, and if one is set as default.

SharePoint Library settings screen for applying retention labels to the library content. Exposing list of available labels for the library.
Even if the visible documents and folder/documentset do not show a label applied now, one could have been applied on a previous version of the item or for items that (appear to) have been deleted.

Action: Check site PreservationHoldLibrary contents for items from the library or folder

This is a hidden system library on the site. To access this library you will need to be Sitecollection Administrator or SharePoint Administrator

add "/PreservationHoldLibrary/Forms/AllItems.aspx" to the end of the site URL.


Action: Check if disposition review is required.

Pre-requisite - related elevated roles or access privileges


When root-cause analysis fails: Cause unknown

THIS IS A LAST RESORT OPTION

If you are confident that triage and analysis failed and direct intervention is required, you can use PowerShell for advanced checks and to force the delete action.


If after all the preceding steps, and you have confirmed its not external services impacting you, and item still won't delete, then you're going to need PowerShell, a decent knowledge of scripting and how SharePoint, Purview and Entra identity management work together.


Action: Run scripts to detect retention labels, legal holds, and checked-out files.

Recommendation: use Microsoft.Graph or PnP.PowerShell module rather than SharePoint module. Microsoft is actively working to move users away from the SharePoint Command Shell options.

Pre-requisite: PowerShell 7.x.x is the recommended for Microsoft Graph and PnP.Powershell modules.


Script Development tips:

  • With nested folders (or documentsets) you will need to use recursive logic and navigation to ensure content and folders are deleted from the bottom-up.


  • For libraries with a lot of documents (i.e. upwards of 10,000 items), you will need to structure your script to process items in batches (usually 200 - 300 items at a good is a good starting point) - to avoid

    • hitting the 5000 items caching limit on views and listing items, and

    • Microsoft throttling the job resources by overloading the service / api call volumes.


  • If you need to remove Retention / Sensitivity labels first you will need to mix-n-match between PnP.Powershll and MgGraph calls.


If you need sample scripts or PowerShell, we recommend AI tools like: Claude.ai, Devin.ai, Copilot for Github and others that can generate functional examples.


Unrecoverable issues

A number of issues can be caused by Microsoft's own services having failures (Incidents), or update-issues (Advisories) - this is particularly important to check for, if you are using integrated services like Purview or Archive.


After triage, if you have identified a critical (unrecoverable) problem you may have to raise ticket with Microsoft directly via the Service health - Microsoft 365 admin center.


In the event you have to do this:


  1. keep your triage action-steps and results documented

  2. if possible, record the output (screen recordings, desktop-shares, powershell log outputs etc)


Be prepared for a frustrating few early conversations while MS Global Support treat you like an idiot, before you get to the product-group and knowledgeable engineers.


Wrap-up

While we know, and acknowledge, that there can also be other causes for blocking a key function like Delete we are not documenting all the possible options and approaches here. If you hit one of the following, you will need professional help from the vendor or a specialist.


Other potential sources of issue can include:


  • Custom script or code developed to supplement workflow, or automates deployed by your company

  • 3rd party component or app deployed to your tenancy sites or library

    e.g. tool to bulk-convert documents to PDF

  • Integrated service which make calls to library

    e.g. External Archive services, or Dynamics connectors

  • Desktop application components which connect or synchronise to and from a library

    etc.


Resources

Support 101


Some root-cause support


Disclaimer

No Generative AI was used in the creation of this article. Topic ideation for content and practical evaluation of the content presented was entirely the author's output. Template, structure and delivery are based on the Spoke support template.


Need help to develop your operational support? Give us a call

If you want to talk about troubleshooting with Microsoft 365 and SharePoint, or need help with the right-way to go about it, contact us at: hi@timewespoke.com


About the author: Jonathan Stuckey

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