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Are you using stock Sigil-2.8.1 or one of the testing builds on Windows that DNSB has built and posted for people? Do you see the same thing on other platforms?
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I was using 2.8.1 Appimage on my linux box when I started using the new procedure you outlined (rather than my old practice of first deleting the old and then adding the new image).
Since then, I've tried to reproduce it on my MacBook without any success.
But on my Windows11 box, using one of DNSB's 2.8.5 test builds (one before the latest), after a few seconds delay, the little extra dialog box appears briefly and then disappears. It's actually hiding behind Sigil's 'OK to replace?' dialog. So you never see it again unless you slide Sigil's box away.
My tests were only with a single image file - not multiple files.
Just checked again with Windows11, the little pop-up notice appears after a few seconds whether using the 'add existing' or whether the image file is just dropped onto the drop-in zone in the staus bar at the bottom of Sigil's window. But you only get a brief glimpse of it before it hides behind the main dialog. Out of sight and out of mind.