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Re:Ask HN: What's the worst piece of software you use everyday? by toyg on Saturday July 11, 2020 @08:52PM (#23807645)
> when I try to upload an image in 2 different conversations (one after another), the second one complains the file already exists

That's because, bafflingly, it uses a local directory-cache for files. Think of it as the "Downloads" folder for a browser. Any time you upload, Teams will try to save it to your local cache first; if it finds the old file, it will whine like that.

Any time you want to upload a file, you should really not do in Chats but in Channels, which have a separate area for each Channel (backed by Sharepoint). Except in some companies (like where I'm now) people for some reason use Chats almost exclusively instead of Channels, so the whole thing becomes awkward: go to the channel, upload, get the link, paste the link in chat.

I guess it could be worse, it could be AOL.

Re:Ask HN: What's the worst piece of software you use everyday? by abhgh on Sunday July 12, 2020 @02:07AM (#23809245)
Thank you for explaining.

If anything, this points to poor use-case study and/or execution. There is a case for channels and for individual chats: details of how files upload happen should be dealt with under the hood.

Frankly, it feels odd even talking about this issue; we are discussing file uploads, worth a few kBs, in a messenger. This really, really, shouldn't be a problem :-)

Re:Ask HN: What's the worst piece of software you use everyday? by tinus_hn on Sunday July 12, 2020 @02:04AM (#23809238)
This sounds as dumb as the Excel ‘you can’t open two files with the same filename’ limitation.
Re:Ask HN: What's the worst piece of software you use everyday? by userbinator on Sunday July 12, 2020 @12:45AM (#23808890)
you should really not do in Chats but in Channels, which have a separate area for each Channel (backed by Sharepoint)

people for some reason use Chats almost exclusively instead of Channels

The fact that there even needs to be such a distinction is itself a problem. They're both conversations, except with some slight differences? That's just asking for confusion.