Macos – Mac OS X’s firewall asks: allow the application “master” network access

It's probably easiest to reinstall iTunes.

If the firewall does not remember your choice, then the digital signature (Code Signing) of iTunes is broken. By default, the OS X firewall accepts any software that was signed by Apple without even asking you. So: it should not have asked you. And once asked, it should be able to remember, based on the digital signature. A broken signature (for example caused by changing the contents of the iTunes.app package) will prevent all this.

(Did you by any chance manually change the iTunes icon the application somehow? Or did you install some plugins?)

You can validate the signature of your iTunes by copying the first line and paste it in Terminal:

codesign -vvv /Applications/iTunes.app/

/Applications/iTunes.app/: valid on disk
/Applications/iTunes.app/: satisfies its Designated Requirement

(More details at If Mac code signing is tampered with, what might fail?)

I had this with using ruby installed via rvm.

This was invaluable and is the correct way I think.

https://web.archive.org/web/20160313182146/http://forums.macnn.com/79/developer-center/355720/how-re-sign-apples-applications-once

I re-signed my rvm/ruby binary and all's well.

Relevant bits:

You can examine the signature information by doing the following:

codesign -dvvvv /path/to/application

Then create a self-signed certificate via the Keychains application that is for Code Signing (see link for details). Then:

Re-signing the application is quite simple.

1. Open Terminal.
2. Type "codesign -f -s (name of certificate) /path/to/application