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Comment by lelandfe | Hacker News Reader

One of my favorite "just why" moments in Teams: let's say I have an image, `foo.jpg`.

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.

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One of the biggest reason I find teams not usable for teams. And so easy to fix, just assume when the user does not want to overwrite the first file that they don't want to overwrite consecutive files.

Aside from the annoyance factor, this is a huge gaping hole allowing information leaks. Let's replace `foo.jpg` with `Annual Review 2021.pdf`. You send employee #1 their review, and then send employee #2 theirs, but forget about this quirk, and instead of keeping, you overwrite. Now employee #1 can open employee #2's confidential info in their link.

Thankfully (I guess?) that isn't a problem: the files are uploaded to Sharepoint folders specific to conversations or channels.

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.

I'll have to verify this tomorrow, but I am 99% certain I have seen this message when sharing the same file name between different 1:1 conversations. I guess it's possible that it is a configuration issue since our Teams/SharePoint is self-hosted at my company.

Yeah, I am not a licensed Microsoft config guy whatsoever, but do know that Sharepoint can be configured to the moon and back. That was, after all, the reason my old org went with Teams over Slack.

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.

Man I hate this. I sort of get wanting to support robust file sharing for teams, but let's be honest: 99% of file uploads on teams are going to be silly gifs.

It is also SO SLOW. It's so slow. Uploading images takes full seconds before they can be sent because Teams has to put them onto Sharepoint first (which itself is slow).

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.

I have stumbled over the same problem and wondered why at minimum it isn't able to recognize that this is the identical file and not ask. Also, it should be able to reshare one file already uploaded.

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