Yes, you can cross-compile on Windows and run on a Raspberry Pi Zero, running Raspberry Pi OS, with some very significant caveats:
1. There are few recent cross-compilers for 32-bit ARMv6 Raspberry Pi 1 boards (including Zero and Zero W). More are available for 64-bit ARMv8 boards such as the Raspberry Pi Zero 2 W, notably the Arm GNU Toolchain. (When did the acronym ARM change to the proper noun Arm anyway?)
2. You will most likely need to install a Posix environment like Cygwin or MSYS2 on your Windows build machine because you will want/need tools like make. You could make do (pun intended) with batch files, but trust me, you don't want to go there.
3. Depending on the particular cross-toolchain you found, you may run into the infamous Windows (and MacOS) filename case insensitivity problem. Horrible example: For some unfathomable reason glibc contains the files xt_CONNMARK.h and xt_connmark.h in the same directory.
4. The biggest caveat is that as soon as you need any library not part of glibc, you will need to cross-compile and install it and all of its dependencies, using the exact same releases as Raspberry Pi OS contains, before you can successfully build your program.
See my Application Note #24 for background information about my adventures with Windows cross-compilers for the Raspberry Pi. In my application (MuntsOS Embedded Linux), I have complete control of both the cross-toolchains and the runtime environment which ameliorates caveats #1 and #4. I have installed both Cygwin and MSYS2 on my windows workstation to solve caveat #2. Windows 10 and 11 have a solution to caveat #3.
The ugly reality is that it is much easier to just install Linux cross-compilers to either Windows Subsystem for Linux or a VirtualBox guest to bypass caveats #1 to #3. #4 remains a difficult problem intrinsic to any cross-compiling scheme.
1. There are few recent cross-compilers for 32-bit ARMv6 Raspberry Pi 1 boards (including Zero and Zero W). More are available for 64-bit ARMv8 boards such as the Raspberry Pi Zero 2 W, notably the Arm GNU Toolchain. (When did the acronym ARM change to the proper noun Arm anyway?)
2. You will most likely need to install a Posix environment like Cygwin or MSYS2 on your Windows build machine because you will want/need tools like make. You could make do (pun intended) with batch files, but trust me, you don't want to go there.
3. Depending on the particular cross-toolchain you found, you may run into the infamous Windows (and MacOS) filename case insensitivity problem. Horrible example: For some unfathomable reason glibc contains the files xt_CONNMARK.h and xt_connmark.h in the same directory.
4. The biggest caveat is that as soon as you need any library not part of glibc, you will need to cross-compile and install it and all of its dependencies, using the exact same releases as Raspberry Pi OS contains, before you can successfully build your program.
See my Application Note #24 for background information about my adventures with Windows cross-compilers for the Raspberry Pi. In my application (MuntsOS Embedded Linux), I have complete control of both the cross-toolchains and the runtime environment which ameliorates caveats #1 and #4. I have installed both Cygwin and MSYS2 on my windows workstation to solve caveat #2. Windows 10 and 11 have a solution to caveat #3.
The ugly reality is that it is much easier to just install Linux cross-compilers to either Windows Subsystem for Linux or a VirtualBox guest to bypass caveats #1 to #3. #4 remains a difficult problem intrinsic to any cross-compiling scheme.
Statistics: Posted by pmunts — Sat Dec 27, 2025 9:22 pm