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Inserting a second shape removed the first: after an insert the new shape stays selected, and `insert.shape` replaced the selection, so each shape replaced the one before. Word draws a new shape beside whatever is selected and never deletes it (checked by hand in Word for Windows: a second shape is drawn over the first, which stays). The new shape now goes after the selection, which is left alone, and becomes the selection. Selected text stays too. A picture still replaces a selected picture, which is what Word does as well (checked in Word for Windows), so `insert.picture` is unchanged. Tests: three shapes inserted in a row are all kept, which fails with the old code (1 of 3 kept); a shape inserted over selected text keeps the text and is selected itself; a picture inserted over a selected picture replaces it. Co-authored-by: Claude Opus 5.5 <noreply@anthropic.com> Co-authored-by: Brandon Thomas <echelon@gmail.com>