Creating Bootable USB with live DEBIAN on MacBook Pro

I have attempted to create a bootable USB with a live DEBIAN image on my MacBook Pro. After about 20 different attempts I have had no success including with Etcher. I have downloaded DEBIAN-live.9.5.0-i386-cinnamon.iso because I want to boot my older iMac from the USB stick. I am never able to come up with a bootable USB drive with DEBIAN. I used the CLI to convert the .ISG into a .IMG and use Etcher to flash the USB.

Etcher indicates that all has worked well and no error messages are received.

I have been able to create a bootable recovery image on the same USB stick. Any comments or suggestions would be greatly appreciated.

Why are you converting the .ISO into an .IMG? You should just be able to write the ISO directly to the USB. If you are simply changing the extension that shouldn’t affect the functionality of Etcher to burn it properly since it should just be doing a raw write.

Make sure your USB is 1.5-2x as large as the ISO you downloaded in case the USB has bad blocks, and make sure your ISO came down completely by verifying the MD5/SHA checksums according to the documentation on the page where you downloaded it.