I’m going to answer my own question here since I think I finally figured it out.
I wasn’t signing gdb
properly. The steps I had been following on line weren’t up-to-date with the moving target that is MacOS’s security requirements.
The command I had been running:
codesign -fs gdb_codesign $(which gdb)
Doesn’t seem to be enough.
What I needed to do was to create an entitlement XML with text like this:
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
<key>com.apple.security.cs.debugger</key>
<true/>
</dict>
</plist>
And then run this command to codesign gdb:
codesign --entitlements gdb-entitlement.xml -fs gdb_codesign $(which gdb)
Finally, I’m able to get the integrated debugging experience in VSCode on MacOS with my native project.