Having ongoing issues with uploading files to an Assignment via Teams Class. Error- "There was a problem attaching this file. Please remove and try again."

Question

Having ongoing issues with uploading files to an Assignment via Teams Class. Error- "There was a problem attaching this file. Please remove and try again."

Mary Surawski 5

Having ongoing issues with uploading files to an Assignment via Teams Class.

-Different Educators different PC's have tried on this class with no luck.

-Tried with both desktop app and web app.

-This team's class has just 1 child. We confirmed their permission is not the issues. Checked by giving that student same access as others in higher grades that successfully use Teams Classes and assignments.

-Made a brand-new class with a Senior Student test account, same issue.

-Educators are not experiencing the same file upload issues with other existing classes.

Please see image attached:

1- File uploaded from my Local (Download Folder). 2.45mb

2- File that has been uploaded directly to this class teams site and attached. 2.45mb

3- Different PowerPoint file from my Local (Download Folder). This is the largest file at 109MB, however the error appeared before this file was added.

4- Image file from my Local (Download Folder). 8.56kb

5- Text from my Local (Download Folder). 2.61kb

Teams - Class_assginment_error

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2 answers

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Answer 1

Mary Surawski 5

1.Try a Different Network Switch to another network and disable VPN if active. -No success

2.Upload via OneDrive Upload the file to OneDrive first, then attach it from there in the assignment. -Error “There was a problem attaching this file. Please remove and try again.” Still occurs

3.Check OneDrive Permissions Ensure OneDrive is accessible and not restricted by your organization. -Tested, not the issue.

4.Clear Teams Cache (Desktop) Quit Teams Go to %appdata%\Microsoft\Teams and delete contents Restart Teams -Completed, even made a new class. -Error “There was a problem attaching this file. Please remove and try again.” Still occurs

5.Check Site Status Make sure the OneDrive site isn’t locked or set to read-only. -Completed, not an issue

6.Upload as ZIP Compress files into a ZIP archive and upload it. Recipients can download and extract it. -Same error

7.Check SharePoint Permissions Confirm that students have permission to upload files in SharePoint. -Tested, not the issue.

8.Update Teams & Browser Ensure both the Teams app and your browser are up to date. Then try using an InPrivate/Incognito window. -Updated and Tested, issue is ongoing.

Ruby-N 10,925 Reputation points Microsoft External Staff Moderator

2025-08-12T20:20:50.98+00:00
Dear @Mary Surawski,

I sincerely apologize for the delay in responding to your feedback. Thank you so much for taking the time to reply and for providing such detailed context about the issue you're experiencing.
It seems that you have already taken all the appropriate measures to try and solve this problem, but unfortunately the problem persists.   I sincerely apologize for the inconvenience and negative experience this may have caused. At this point, the best course of action would be to contact Microsoft support directly. A support engineer can conduct a remote session to investigate the situation, verify the back-end configurations, and run the necessary synchronization tools to resolve the issue.

As forum moderators, we do not have access to the detailed logs or backend systems needed to fix this issue effectively due to privacy and security limitations. For that reason, the most efficient solution would be to contact Microsoft's support team directly.

We sincerely recommend you try to create a support ticket from Microsoft 365 Admin Center>Support>Help & Support.

You can raise support ticket from: Microsoft 365 admin center 

For reference: Get support - Microsoft 365 admin | Microsoft Learn

Phone Support: Microsoft provides customer service phone numbers based on your region. You can find the appropriate contact number here: Customer service phone numbers - Microsoft Support 

While I regret that I cannot offer a more immediate solution, I will continue to support you in any way I can throughout the process. Once you have successfully created a support ticket, feel free to share the ticket tracking ID with me in Private Message. This will allow me to monitor progress on your behalf and help ensure that the issue is addressed in a proper and timely manner.

To view or send private messages, sign in to the Q&A forum using the account that posted this thread, then click Private Messages.

Looking forward to your response so I can assist you more effectively. Thank you very much for your understanding and your cooperation.

Answer 2

Dear @Mary Surawski,

Welcome to the Q&A Community.

We appreciate you taking the time to share a detailed explanation of the issue. Based on your description, I'd like to offer the following insights and recommendations to help address the issue.

You can attach up to 10 resources per assignment. Maximum file size per resource is 500MB

Supported attachment methods include Device, OneDrive, Class Notebook, Link, and apps like Flip or Wakelet.

For reference, you may check this link: Attachments for an assignment in Microsoft Teams for Education - Microsoft Support

You can refer to the workarounds listed below:

1.Try a Different Network
Switch to another network and disable VPN if active.

2.Upload via OneDrive
Upload the file to OneDrive first, then attach it from there in the assignment.

3.Check OneDrive Permissions
Ensure OneDrive is accessible and not restricted by your organization.

4.Clear Teams Cache (Desktop)

Quit Teams

Go to %appdata%\Microsoft\Teams and delete contents

Restart Teams
For reference, please check this link: Clear the Teams client cache - Microsoft Teams | Microsoft Learn

5.Check Site Status
Make sure the OneDrive site isn’t locked or set to read-only.

6.Upload as ZIP
Compress files into a ZIP archive and upload it. Recipients can download and extract it.

7.Check SharePoint Permissions
Confirm that students have permission to upload files in SharePoint.

For reference, please check this link: Customize SharePoint site permissions - SharePoint in Microsoft 365 | Microsoft Learn

8.Update Teams & Browser
Ensure both the Teams app and your browser are up to date. Then try using an InPrivate/Incognito window.

You can try these workarounds and update us. If the issue still appears please feel free to let us know and we will keep assisting you. Please know that we truly appreciate your patience and understanding as we strive to support you. We are here to help. Thank you very much for your understanding and cooperation.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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Ruby-N 10,925 Reputation points Microsoft External Staff Moderator

2025-07-30T23:07:13.4033333+00:00

Hello @Mary Surawski,

I hope this message finds you well.

I just wanted to follow up regarding the issue you reported earlier. I shared some possible solutions with you a few days ago, and I wanted to check in to see if they helped enhance your workflow and productivity.

If you're still experiencing the issue or need further assistance, please don't hesitate to let me know. I'm here to help and would be happy to continue supporting you.

Looking forward to your response!

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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Ruby-N 10,925 Reputation points Microsoft External Staff Moderator

2025-07-31T21:22:44.5066667+00:00

Hello @Mary Surawski,

Just checking in again regarding your previous support request. I haven’t heard back yet, so I wanted to see if you're still encountering the issue.

If you could share any updates or additional details, I’d be happy to assist further.

Thanks, and I look forward to your reply.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

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Having ongoing issues with uploading files to an Assignment via Teams Class. Error- "There was a problem attaching this file. Please remove and try again."

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