Sorry to hear about this problem. It seems strange that the site would generate this kind of error. However I am curious to learn if you happen to refresh the page and try to upload again if this works as expected?
Also, have to tried to add attachments to this issue when not looking at it directly on this new board popup view? I am curious to learn if the problem persists when viewing the issue directly, as opposed to on that active sprint board.
Have you also tried this with other browser to see if this happens? I tried the recreate this problem with my version of Chrome on my Cloud instance, but I could not seem to do so. So I am interested to learn if we can focus on what might be different with your environment that might be a factor in this problem.
Are any other users of your Cloud site reporting this same problem?
If you can still repeat this problem, I would be interested to see if you can generate a HAR file when this upload failure happens. This could be helpful to us in order to understand if there is something wrong with the browser, or the site, or the request itself being made.
If the problem is not still happening, then the HAR file won't be helpful. If you can still reproduce this, then perhaps we can learn more about the problem from the HAR. Sorry, but I'm afraid our community site won't permit attachments at this time. You could upload this to a site like drop box, or to a google drive account and then share the file publicly that way to get it to us.
If you have concerns about privacy, (I don't think there is anything sensitive in the HAR file itself), just let me know. We could create a support request if need be where you can upload this to Atlassian support privately.
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