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I've never had an issue working in Illustrator like this before, I have Illustrator 28.5, macOS Sonoma 14.4.1:
Usually when I group items together, I'm able to scale them proportionally when I’m using Selection Tool (V) and clicking Shift to scale, or I would make the entire thing smaller proportionally by using Option+Shift to scale from both sides at once. Now, I’m in Illustrator and my items are grouped, but the font boxes are just pushing into each other in a weird way that makes no sense rather than scaling together.
I saw feedback on some other posts to reset their preferences, and I already did that and restarted. I also tried to turn off smart scaling, and nothing changed. I also have my bounding box on.
Here's some screenshots of what's happening when I try to scale either of those ways I listed above while these are grouped
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I labled color coded each of the different text boxes with the names 1, 2 and 3, and made them different colors to make it more clear what's happening
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Can you share a sample Illustrator file for inspection?
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Here you go! It's the same file I used to screenshot the issue
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Thank you, but the attachment is missing.
Try to save and attach a .pdf file with the "Preserve Illustrator Editing Capabilities" option turned on.