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Re:Students are failing AP tests because the College Board c... by Thorrez on Friday May 22, 2020 @01:55AM (#23269052)
There's a medium option: have an alert popup saying

    Convert the image to a format the site accepts (jpg)?

    [ ] Don't show this message again

    [OK] [Cancel]
Re:Students are failing AP tests because the College Board c... by lightgreen on Friday May 22, 2020 @04:43AM (#23269910)
Anecdotally, yesterday I accidentally learned that my relative clicks OK in any dialog window within 200ms without even attempt to read the message. So the alert you suggest would slightly help 1% of geeks and will annoy 99% of the users.
Re:Students are failing AP tests because the College Board c... by Thorrez on Friday May 22, 2020 @09:01PM (#23278827)
Compared to the option of not converting, it would help everyone, reducing annoyance.

Also I'm not sure if you can generalize from your one relative to 99% of users.

Re:Students are failing AP tests because the College Board c... by LordDragonfang on Saturday May 23, 2020 @04:46AM (#23281247)
While it may not be 99%, /r/talesfromtechsupport on reddit has enough instances of this to suggest it is extremely common user behavior.