Skype File Transfer: Dealing with the “Gotchas”

One of the most frequent questions I have encountered recently relates to using Skype File Transfer in a Group Chat. One came recently from an acquaintance whom I was advising on using Group Chat for his business team comprising eight colleagues. In particular, the questions are based around why a File Transfer works for some contacts in a Group Chat session but not others. And, as I learned earlier this week, there’s not just one answer.

As background I usually initiate a file transfer by dragging a file from a Windows Explorer folder to the Skype chat text entry pane.

So why do they not transfer successfully to all members participating in the Group Chat?

First, to be eligible to receive and store a file shared through the Group Chat a Contact in the Group must also be an “accepted” individual Contact of the user who is sending the file. If you are not an “accepted” Contact of the sender the file transfer will fail.


But even if you meet this condition you can still get an error message.

The hotfix Skype for Windows not only addresses a stray Instant Messaging/chat message issue that was well publicized but also addresses an issue where the disk or device to which the file was being stored had the FAT 32 format. At this stage in the evolution of Windows where most PC’s use the NTFS disk format this was probably occurring mostly where the file was being stored on a removable storage device such as a USB memory stick.

But the group I was supporting still had an issue where, say, four members would be able to save the file successfully while a couple of others, who were direct contacts of the sender, got an error message when they tried to save the file.

To isolate the issue from performing the file transfer in a Group Chat I had a direct chat conversation with one individual who was getting the error message. The problem still occurred. I then brought Skype screen sharing into action to watch what was happening on her Windows desktop.

It turns out that the error message is triggered by attempting to save a transferred file in a folder where there is already a file with the same name. This error message appears after responding “Yes” to the dialog box warning about overwriting a file. Change one character in the file name and the file can be saved. Here is the example my Contact was encountering:


Note that three months ago she had saved a file. When she tried to overwrite this from a file transfer with the same file name she received an error message. When she added the “2′” to the file name she was able to save the file.

While this Skype file transfer issue has a simple fix as shown above, it has been reported to Skype and hopefully will be addressed in an upcoming release. It has been reproduced by a third party contact.

About Jim Courtney

Bringing over thirty years' experience in the sales, marketing and management of cutting edge technology businesses.

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