Failed to send Error

Question

Within the last three weeks several users in my organization have been unable to share/send files within private chat/group messages within Microsoft Teams. When they attach a file in a Teams Chat, they get an error, "Failed to Send."

We have tried sending files (of different types and sizes) through the Desktop Application and the Web application and both platforms return the same message "Failed to Send" On multiple OS (iOS, Linux, Windows) and browser (Chrome, Edge, Firefox) versions. It does appear however that we are able to attach files through the Mobile App.

The Files appear to upload to OneDrive just fine and if we attempt to reattach and send the file we get the message "File Already Exists."

We are able to send files within a Team Channel, but not in private Chat Messages to each other. Additionally Opening OneDrive to the location where the file is stored and attempting to share the link generated by SharePoint also seems to work. The error appears to live within the Teams interface.

Starting chats and sharing files with other users works. However when the user experiencing the issue joins that chat file sharing ceasing to function.

The issue is almost assured to be an account related issue, however, there appears to be no noticeable corruption to the users account and all other functions of the account are working perfectly fine.

Have been trying to find a solution but nothing has worked. Any help would be incredibly helpful. Of note, I have admin access.

Answer 1

Hi Vincent,

I encountered the same problem where all my attempt to share a file in a 'Group Chat' (NOT a Teams Channel) were failing, since the time I was added to this chat.

This morning, I had a detailed chat with our Organisational IT Help Desk and even they didn't notice any problem with any set up. Hence, they could not help either.

Later, I tried something different, which worked. Here's what I did.

1. Rather than just drag and drop the file, I clicked on the "Paper clip" icon below the message window and selected the file that I wanted to share.
2. Then, instead of hit ENTER; I clicked the 'tiny downward pointing arrow' next to the file name; which opened the 'link sharing options, pop-up dialogue box'.
3. The default option was 'share with everyone in the organisation' and 'Editing' was Unchecked.
4. I changed the sharing option to 'Everyone in this Group chat' and Checked the Editing option.
5. Then, when I hit ENTER, the file was shared instantly.

I haven't tried other combinations of link sharing options, so not sure if this was the only way it would have worked or not.

What intrigues me is that I have 6 similar Group Chats with different departments, where I am meant to be sharing a file each month. And, except for this particular Group Chat, I have never had any problem sharing files in any other Group Chats.

When I advised of the above work-around to IT, they had no explanation for this anomaly. They confirmed that while they do set certain restrictions in relation to file sharing in Teams Channels, they do not do it for Group Chats. Hence, every member of the group is meant to have exactly the same authorisation.

Anyway, I hope my work-around helps others. And, I would also appreciate if someone else in the community can provide a valid explanation for this anomaly.

Regards,

Kalpesh

Answer 2

I am having the same issue but only with 1 of my accounts which I can send images in group chat on the mobile app, but on the desktop both app and web I get this error. However when I tested on my 2 other business accounts and my personal account they were fine.

Not sure whether this is Win11 related or what but this issue only started popping up after I upgraded to Win11 and it's odd that my 3 other accounts do not have this error.

Answer 3

Hi Vincent,

Is there something common between the people who can't send files to eachother? For example, is there always at least 1 Guest involved in the chat when it fails?

I am having an issue where 1 Guest is involved in a group chat and it results in issues sharing attachments when the default tenancy sharing option is set to 'Share with everyone in the organization'. The default behaviour is that a Member attempts to send a file to a Guest, but as a Guest they are 'not in the organization', so the user needs to change their selection to 'share with specific people'. They can do this on most file types, but not image file types, which is an issue we are also having. I am thinking we need to change the default sharing option to 'specific people'...

Answer 4

Hi, Vincent,

My name is Didi. I'm happy to help you today.

Sorry to hear you're experiencing this issue. This could be related to the service degradation issue regarding the inability to see previously uploaded images or upload new images. You can find the advisory in the Microsoft 365 admin center 'Service health'.

https://admin.microsoft.com/?auth_upn=chean%40A...

Nonetheless, affected users can still try clearing the Teams cache and see if there's any difference.

For Windows:

https://answers.microsoft.com/en-us/msteams/for...

For Mac:

https://eshop.macsales.com/blog/68682-clear-mic...

If the issue persists, I suggest reporting the issue by clicking on the Help icon > Report an issue.

Disclaimer: The second link above is a non-Microsoft website. The page appears to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it.

Best regards,