Homebrew and Apple Silicon Macs

While kicking the tires on Autogram’s content tool¹ Spidergram I ran into a puzzling error:

Error: dlopen(/Users/markllobrera/git-workspace/ammp-spidergram/node_modules/canvas/build/Release/canvas.node, 0x0001): symbol not found in flat namespace (_cairo_fill)
    at Object.Module._extensions..node (node:internal/modules/cjs/loader:1361:18)
    at Module.load (node:internal/modules/cjs/loader:1133:32)
    at Function.Module._load (node:internal/modules/cjs/loader:972:12)
    at Module.require (node:internal/modules/cjs/loader:1157:19)
    at require (node:internal/modules/helpers:119:18)
    at Object.<anonymous> (/Users/markllobrera/git-workspace/ammp-spidergram/node_modules/canvas/lib/bindings.js:3:18)
    at Module._compile (node:internal/modules/cjs/loader:1275:14)
    at Module._extensions..js (node:internal/modules/cjs/loader:1329:10)
    at Object.require.extensions.<computed> [as .js] (/Users/markllobrera/git-workspace/ammp-spidergram/node_modules/ts-node/src/index.ts:1608:43)
    at Module.load (node:internal/modules/cjs/loader:1133:32) {
  code: 'ERR_DLOPEN_FAILED'

A few dozen browser tabs later it appeared that this was related to dependencies that were not compatible with ARM64, aka the architecture used by the new Mx series of Apple silicon. Further investigation revealed that it wasn’t just Spidergram’s NodeJS package dependencies, but the Python dependencies underneath.

[Deep Breath]

My initial instinct, as is typical for me, was to set my machine on fire and renounce this career.

I slept on it instead, and here was what I found:

• I had used Migration Assistant to go from my Intel-based MacBook Pro to this M1-based Pro, and that meant that my Homebrew formulae were a mish-mash of Intel 64 and ARM64 versions
• My installed version of Python was pretty old, 2.7.x-era

To clean this up:

• I reinstalled Homebrew to /opt/homebrew using the default instructions
• Added /opt/homebrew/bin to my $PATH
• Created a Brewfile using brew bundle dump in /usr/local/bin, and then copied this file over to /opt/homebrew/bin
• Made sure I was using the new brew: which brew, pointing to /opt/homebrew/bin
• Ran brew bundle in the dir with the Brewfile to install my formulae into the new Homebrew bin
• I used pyenv to install the latest Python version, pyenv install 3.11.2

After all that I was able to run npm install within my Spidergram project and those dependencies now pointed to the latest Python version.

All of this reminded me of Alex Riviere’s recent post, “Delete Your Dev Environment Regularly”. I think if I had to do things over I would have chosen not to use Migration Assistant and reinstalled my tooling from scratch.