fwiw, VSCode is very impressive. I often forget I'm using an electron app.
I share it once and it gets uploaded to Sharepoint (as `foo.jpg`). This happens even if you're just sharing a funny image in a private message. It gets uploaded to Sharepoint. Ugh.
Anyway, let's say I share the same image again. Teams says "hey do you want to overwrite `foo.jpg`, or keep the existing one?" I select keep. Teams now creates `foo-1.jpg`.
We're already off to a bad start, but bear with me. Here's where it gets amazing:
1. I share `foo.jpg` a third time.
2. Teams says "Do you want to overwrite or keep?" I select keep.
3. Teams then again asks "Do you want to overwrite or keep?", because `foo-1.jpg` is taken. I select keep.
4. Teams tries to create `foo-2.jpg`. Return to step #2 until an unused integer is found.
That chain of dialogs can continue for a while for common file names on large teams.
For those still on Teams, my condolences, here's a workaround: copy the image onto your clipboard and paste it into the textbox. It skips the uploading to Sharepoint, prevents the issue I described, and is sendable in milliseconds. Downsides: a. they're randomly ephemeral and sometimes just permanently disappear, b. no animated images - it'll just send the first frame of a GIF/APNG/etc.
And for those on macOS, that means you can get screenshots sent quickly. Ctrl-Cmd-Shift-3, Cmd-V into the text field. Send.
So the issue I detailed would only rear it's head in your scenario if you sent employee #1 their review twice.
Humorously, this issue does not occur when uploading files directly in the Sharepoint interface – despite the interface looking like it stepped out of Windows 95.
So it's not hard for me to imagine that it could be set up in a way that causes this issue across discussions. Yuck.