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Re:Show HN: 8086/8088 assembler that runs over 8088 hardware... by WalterBright on Thursday October 03, 2019 @03:44PM (#21151254)
Digital Mars C and C++ compilers still support 16 bit 8086 code generation and are free:

https://www.digitalmars.com/download/freecompiler.html

Source code to the compiler/libraries is also free:

https://github.com/DigitalMars/dmc

https://github.com/DigitalMars/Compiler

Re:Show HN: 8086/8088 assembler that runs over 8088 hardware... by zokier on Thursday October 03, 2019 @04:41PM (#21151950)
Re:Show HN: 8086/8088 assembler that runs over 8088 hardware... by pan69 on Thursday October 03, 2019 @06:08PM (#21152787)
> The toolchain can be used on either a GNU/Linux® or Microsoft® Windows® host.

Bingo. I love programming for early DOS systems (86, 286, 386) but it's difficult to find a tool-chain that runs on Linux and is able to produce DOS compatible binaries. I think OpenWatcom might but I could not get it to work correctly.

Definitely going to give this a try.

Re:Show HN: 8086/8088 assembler that runs over 8088 hardware... by h2odragon on Thursday October 03, 2019 @09:30PM (#21154052)
If you have not yet done so, may I suggest you investigate 'Dessqview/X'. Lovely stunts there.