A quick Google turns up https://web.csulb.edu/~murdock/submenu.html , which states you can only have nine SUBMENU commands per block. You have eleven SUBMENU items in your first block. Perhaps it will behave if you cut that down to nine?

I did just that by taking some submenu entries out and making a new parent menu entry for those excess ones, still doesnt work, it looks exactly the same in the screenshot above EDIT: Not exactly the same in the screenshot but some entries shifted because I added some for the excess submenus. EDIT 2: The config.sys and autoexec.bat look like this now (see attachments)

It's also not entirely clear if the equal sign is necessary for the syntax. See http://web.archive.org/web/20030701054111/htt … elp/submenu.htm (linked from Adding Text to Config.sys for Menus ).

I attempted to do something similar to this but still, no dice, config.sys says "submenu" is invalid. EDIT: It does work! This is the solution! Here is an example:

1[MENU] 
2SUBMENU=TOOLS
3MENUITEM=SOMETHING
4
5[TOOLS]
6SUBMENU=1
7SUBMENU=2
8
9[1]
10(junk)
11
12[2]
13(junk)
14
15[SOMETHING]
16(junk)

Basically, every menu that has a submenu is defined as a submenu and then the actual submenu item goes under the items that the parent menu launches. It's complicated, I can't explain very well, but the example will serve well.