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I am trying to setup the iPad as a development station. Managed to ssh from it to my Mac, but the thing is, on the Mac I need to connect to a VPN to be able to access some websites. Those websites would be accessible from the Mac, and I would like to use the Mac as a proxy somehow, so that also the iPad would be able to have access to the same kind of resources.

Does anyone have any tips as to how I could get them to work on the iPad?

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  • Why don't you simply set up a VPN-connection on your iPad?
    – klanomath
    Commented Nov 21, 2019 at 11:08

3 Answers 3

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I have a similar situation and resolved it by setting up a VPN client on the iPad so that it connects directly to those addresses.

  • The built in VPN client in IPSec mode works great with Cisco.
  • The L2TP works great with most standard commercial VPN solutions (like Meraki)
  • OpenVPN works with many consumer grade VPNs (like NetGear Orbi)

Doing this allows me to use the iPad directly with remote resources behind my company or home firewall.

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  • Could you go a bit more into specifics as to how you configured everything?
    – Geo
    Commented Nov 17, 2019 at 23:09
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If your VPN is a "tunnel-all (traffic)" VPN, and runs as software on your Mac, which most are, it's not going to be possible to get your iPad to connect to it / the tunnel.

Most VPNs establish a routing rule that renders local WiFi devices (other hosts, WiFi printers, etc.) unavailable. I live this life nearly 24/7 which makes my work machine unsuitable for anything with personal use, even things that involve communication between my work phone and work laptop (eg. Handoff) which is particularly obnoxious.

In the (low) chance that your VPN is via an external ethernet-wired hardware device, you should be able to accomplish this via MacOS' built in "Internet Sharing" (System Preferences -> Sharing, Internet Sharing checkbox.) Your iPad would then connect to the WiFi provided by your Mac, rather than the wireless router that everything else connects to.

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  • Thing is, I would like to leave the mac at home, and connect via the ipad, from somewhere else in the city, using a different wifi network.
    – Geo
    Commented Nov 21, 2019 at 22:47
  • Your requirements are growing significantly, and your manner of making the iPad dependent on the Mac for development is difficult. At some point you’re just going to be doing something like using a Remote Desktop client on your iPad in order to use your Mac.
    – Jason Salaz
    Commented Nov 21, 2019 at 23:10
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I would like to use the mac as a proxy somehow

You've said "proxy" — it means you're half-way there:

  • Proxy has to be run on Mac1;
  • iPad should be configured to use it.

As often happens similar things are already done by someone and are on Internet, check it out: "How to connect an iOS device to your computer via a SOCKS proxy".

I'll add a small adjustment though.

On your Mac you can run this SHELL-command: ssh -N -gv -D 1080 127.0.0.1 — it simply connects over SSH to Mac itself but it has a side effect: it opens up TCP/IP ports2 1080 which would become gates to SSH's own Socks-proxy3.

Configuring iPad to use Socks proxy shouldn't cause any troubles and is described by the link I've given as well.

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  1. If your SSH software on iPad supports Socks proxying you can avoid running proxy on server itself. But beware that Socks proxy endpoint would be iPad, so when you configure a browser you should be using iPad's local IP 127.0.0.1.

  2. Port would be bound to all network interfaces of Mac thus meaning you can connect to it from your LAN — unless there's a firewall, of course.

  3. It's not only possible way to get Socks proxy on your Mac, but likely the most fast and simple one.

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  • I tried to do this setup. I ran the ssh command, and configured the ipad to use the .pac file as served from dropbox. I can still access websites from the ipad, however, nothing is logged in the terminal window where ssh is running. Also, I started the VPN connection on the mac, but the ipad is not able to access the protected websites. Any idea what I might be doing wrong?
    – Geo
    Commented Nov 21, 2019 at 22:46
  • verify setup in steps: 1) try checking proxy first on Mac itself. Enter 127.0.0.1 (because SSH's Socks is listenings locally on loopback too) and its port number 1080 in systems settings of proxy. Or you can use Firefox because currently it’s the only popular browser available for MacOS that supports not only system-wide settings for proxy there, but any custom one too.
    – poige
    Commented Nov 22, 2019 at 8:44

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