QEMU and binfmt support light the way :)
https://github.com/microsoft/wsl/issues/2468#issuecomment-374904520
After reading that the WSLInterop between WSL and Windows processes used binfmt, I was tinkering with QEMU to try some ARM development, and incidentally discovered how to get 32-bit support working.
Edit: requires "Fall Creators Update", 1709, build 16299 or newer
Install qemu and binfmt config:
sudo apt install qemu-user-static
sudo update-binfmts --install i386 /usr/bin/qemu-i386-static --magic 'x7fELFx01x01x01x03x00x00x00x00x00x00x00x00x03x00x03x00x01x00x00x00' --mask 'xffxffxffxffxffxffxffxfcxffxffxffxffxffxffxffxffxf8xffxffxffxffxffxffxff'
You'll need to reactivate binfmt support every time you start WSL:
sudo service binfmt-support start
Enable i386 architecture packages:
sudo dpkg --add-architecture i386
sudo apt update
sudo apt install gcc:i386
Try it out:
$ file /usr/bin/gcc-5
/usr/bin/gcc-5: ELF 32-bit LSB executable, Intel 80386, version 1 (SYSV), dynamically linked, interpreter /lib/ld-linux.so.2, for GNU/Linux 2.6.32, BuildID[sha1]=2637bb7cb85f8f12b40f03cd015d404930c3c790, stripped
$ /usr/bin/gcc-5 --version
gcc-5 (Ubuntu 5.4.0-6ubuntu1~16.04.9) 5.4.0 20160609
Copyright (C) 2015 Free Software Foundation, Inc.
This is free software; see the source for copying conditions. There is NO
warranty; not even for MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.
$ gcc helloworld.c -o helloworld
$ ./helloworld
Hello, world!
$ file helloworld
helloworld: ELF 32-bit LSB executable, Intel 80386, version 1 (SYSV), dynamically linked, interpreter /lib/ld-linux.so.2, for GNU/Linux 2.6.32, BuildID[sha1]=3a0c7be5c6a8d45613e4ef2b7b3474df6224a5da, not stripped
And to prove it really was working, disable i386 support and try again:
$ sudo service binfmt-support stop
* Disabling additional executable binary formats binfmt-support [ OK ]
$ ./helloworld
-bash: ./helloworld: cannot execute binary file: Exec format error