Having installed a Traxide kit, and then going back later to install a coax antenna cable for the UHF radio, I can recommend the following tip to get cables through that driver's side grommet.
Pull the grommet out from the engine bay side. In my case, no chance of losing it as the Traxide cables were already through it. It's much easier to stretch the opening for the second cable. Once threaded through the firewall, it's easy to push the grommet back in place.
If at first you don't succeed, that's one data point. - xkcd
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2011 Discovery 4 SDV6 HSE
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