I've followed all the advice on these forums regarding developing network extensions. I'm working on a FilterDataProvider using the SimpleFirewall example project as a starting point. The issue I run into is that the copy of the extension binary that the system manages does not get updated by the system when I copy a new application into the /Applications directory. Here's my workflow: Build and run the application from Xcode. I've added a pre-run action that copies the extension into a /Applications/SysExtDev folder so I don't have to disable SIP. Test & make changes to code Disable & remove the extension in Settings > Network > Filters & Proxies Build and run the application from Xcode. New app binary loads, but the old extension binary loads. I also notice that the app will report that the extension is already registered even when it's not present in the UI in System Settings. And when I enable the extension in the newly launched app, I don't see the full flow of confirmation dialogs, only one indicating that the app wants to filter network content. If I run: ❯ diff /Applications/SysExtDev/SimpleFirewall.app/Contents/Library/SystemExtensions/com.example.apple-samplecode.SimpleFirewall2U6G6353D3.SimpleFirewallExtension.systemextension/Contents/MacOS/com.example.apple-samplecode.SimpleFirewall2U6G6353D3.SimpleFirewallExtension /Library/SystemExtensions/44022C0D-8BBA-4783-8314-83195A516DB5/com.example.apple-samplecode.SimpleFirewall2U6G6353D3.SimpleFirewallExtension.systemextension/Contents/MacOS/com.example.apple-samplecode.SimpleFirewall2U6G6353D3.SimpleFirewallExtension Binary files ... and ... differ it indicates that the binaries are not the same. In order to resolve this issue I usually have to wait around for awhile and/or reboot the machine. I can't find any rhyme or reason to it. I've tried removing the old app from /Applications before building the new copy but that doesn't seem to help either. The way I know things are going to work is, if when I launch and enable the extension, I see the full onboarding flow asking me to open settings and allow under privacy and security. I have tried running $ systemextensionsctl uninstall 2U6G6353D3 com.example.apple-samplecode.SimpleFirewall2U6G6353D3.SimpleFirewallExtension but that requires SIP to be disabled. I'm really close to just throwing in the towel and developing with SIP disabled. However, I feel like I must be missing something. Do I need to bump the version every time? Do I need to kill the extension process with launchctl so it can be cleaned up? Do I have to tickle the launch services or sfl db? What am I missing?