I hit this just now and found this thread because I was trying to understand why it was stuck on this forever, when I haven't had other problems. I don't have an answer to that question, but I tried unplugging the cable and then plugging it back in while on that alert and that seemed to break it out of the loop it was stuck in, so maybe give that a shot. It switched over to "Copying shared cache symbols from iPhone" after that and completed installation.

I don't know if it will work for your case, but this may work for you: Settings > General > Reset > Reset (button) > Reset Network Settings (your phone will restart and you will be logged out of your access points, so have your password written down/handy) Set up your access point again. Set up your manual proxy again. Launch your app to trigger allow connection prompt. If you're using a third party proxy, fetch the SSL certs again. Trust the certs again. Relaunch the app and now it should work. This also is the ONLY thing that has worked for me when I encounter the iOS bug where iOS refuses to embrace the proxy config no matter how set up it (fakely) appears to be. You can uninstall and reinstall your certs until the end of time, but if it won't connect to Charles or Proxyman or whatever you're using, it's not going to ever work. Reset your network settings. It's the only way I've found to de-confuse iOS.