I'm not entirely sure this fix is correct. I have not tested, but AFAUI this will no longer allow changing the upload method using the "menu" entries using older arduino-cli, since you now set a new-style upload tool for the board as a whole, but no (new-style) tool for the menu entries (only old-style tool lines, but those are not converted in 0.21).

IOW, I think you need lines like below (instead of the ones you added now):

Nucleo_144.menu.upload_method.MassStorage.upload.tool.default=massStorageCopyNucleo_144.menu.upload_method.swdMethod.upload.tool.default=stm32CubeProg

Also, might be good to mention the full range of affected arduino-cli versions, looks like this problem was introduced in 0.19 withpluggable discovery, it was already working before that.

I'm not entirely sure this fix is correct. I have not tested, but AFAUI this will no longer allow changing the upload method using the "menu" entries using older arduino-cli, since you now set a new-style upload tool for the board as a whole, but no (new-style) tool for the menu entries (only old-style tool lines, but those are not converted in 0.21).

In fact with IDE it works but not with the cli.

IOW, I think you need lines like below (instead of the ones you added now):

Nucleo_144.menu.upload_method.MassStorage.upload.tool.default=massStorageCopyNucleo_144.menu.upload_method.swdMethod.upload.tool.default=stm32CubeProg

Unfortunately this is not recognized properly. I guess no fix can be provided for this.
So upload will simply not be compatible with arduino-cli version started from 0.19.0 to 0.21.0.

Now I wondering if we could use the pluggable discovery feature....