In a chat with Apple support, I was told my iPod is no longer supported.

iTunes refuses to show it in the list of devices. Clearly the Mac recognizes it as an iPod and a working USB device. It also shows up on the desktop as a volume. The iPod shows up in the System Report as a USB device. This version of Apple Ipod 160GB - Classic Ipod 160GB Manual compatible with such list of devices, as: Ipod 160GB - Classic Ipod 160GB, iPod iPod. It's the Classic 160GB (the best iPod ever). gen 6 has a limit of 128gb when restored w itunes, can be overcome by after. currently running an i flash quad w 4 512gb tf cards,in a 160gb thin (gen 7) ipod works fine w itunes and the stock os as well as w rockbox. Excludes: Alaska/Hawaii, APO/FPO, US Protectorates, Angola, Burundi, Benin, Burkina Faso, Botswana, Central African Republic, Côte d'Ivoire (Ivory Coast), Cameroon, Congo, Democratic Republic of the, Congo, Republic of the, Comoros, Cape Verde Islands, Djibouti, Algeria, Egypt, Eritrea, Western Sahara, Ethiopia, Gabon Republic, Ghana, Guinea, Gambia, Guinea-Bissau, Equatorial Guinea, Kenya, Liberia, Libya, Lesotho, Morocco, Madagascar, Mali, Mozambique, Mauritania, Mauritius, Malawi, Mayotte, Namibia, Niger, Nigeria, Reunion, Rwanda, Senegal, Saint Helena, Sierra Leone, Somalia, Swaziland, Seychelles, Chad, Togo, Tunisia, Tanzania, Uganda, South Africa, Zambia, Zimbabwe, Afghanistan, Armenia, Azerbaijan Republic, Bangladesh, Bhutan, China, Georgia, India, Japan, Kazakhstan, Kyrgyzstan, Korea, South, Sri Lanka, Maldives, Mongolia, Nepal, Pakistan, Tajikistan, Turkmenistan, Uzbekistan, Aruba, Anguilla, Netherlands Antilles, Antigua and Barbuda, Bahamas, Belize, Barbados, Costa Rica, Cayman Islands, Dominica, Dominican Republic, Guadeloupe, Grenada, Guatemala, Honduras, Haiti, Jamaica, Saint Kitts-Nevis, Saint Lucia, Montserrat, Martinique, Nicaragua, Panama, Puerto Rico, El Salvador, Turks and Caicos Islands, Trinidad and Tobago, Saint Vincent and the Grenadines, British Virgin Islands, Virgin Islands (U.S. Apple iPod iPod classic Seventh Gen 160GB User Manual Download Operation & user’s manual of Apple Ipod 160GB - Classic Ipod 160GB MP3 Player, Other for Free or View it Online on . gen 2 - doesnt work (firewire) gen 3 - up to 256gb cf card (must transfer/restore over usb) gen 5 - 1tb.

Ipod classic 160gb 8th generation