I was having the same issue, and it didn't offer the "always allow" option, only "allow". The way I found to fix this was to find the certificate you are using to sign the app during the build process in Keychain Access, expand it to show the signing key, right click on the key and choose get info. Go to the access control tab, and you have one of two options: Choose "Allow all applications to access this item" (not secure) Choose "Confirm before allowing access" and add "codesign" and "Xcode" to the list of allowed list of applications. (you'll need to do a global search to find where codesign resides on your machine) After this, you will no longer get the repeated password prompt.