Microsoft has such impressive research and such great developers. Makes it all the more frustrating what their products end up like (I’m guessing due to leadership).
"Need to make money" is the main reason, actually. Leadership are merely running after that.
It's like they thought that keep improving on the things they work would make them hit a ceiling so instead of steadily climb they take one step back to delay the climb.
And the reason why I think it's deliberate is because none of their other products follows that pattern: Azure faces fierce competition so you cannot afford to stumble, C# is amazing compared to Java at least, Office has alternatives breathing on their back, VS Code... used to have competition but now that it's super popular I'm scared it'll be the next product to follow the "Windows progression pattern".
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.
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.
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.