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In 15.1.2 on mac. Used to be able to resize photos very easily for years, or maybe a decade. Hold shift/command, with selction tool, resize. Simple. Now it does not work anymore. Restarted my computer three times because I thought something was wrong. Can resize with direct selection tool but works terrible then have to resize the bounding box in what is just an utter pain. What am i missing??
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Did you try a reset of preferences and restart?
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In addition to what Mike suggested, there may be an application or browser extension which is "capturing" your modifier keys (like an antivirus application or other app). To test for this reboot your computer. Turn off autoloading startup applications, OPEN INDESIGN FIRST and try resizing with Command/Shift. If it now works, this is the source of the problem. Then watch carefully as you load other applications to see where the culprit is.
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For testing purposes only, try each key by itself, then try them in combinations, and also try the keys on both sides of the keyboard.
~ Jane