So, seems I have figured out the issue (at least on my Lenovo T460s) and
I think it lies with the Intel chip internal GPU.

If you use display port and HDMI-->Display Port adapter it won't work.
The Intel chip doesn't seem to support two DP connections at a time. But
you can connect Dp & HDMI-->DVI at the same time (or VGA for that
matter) & Internal display. So max is 3 displays but they need to be
different techs.

I can't confirm this for other laptops without external graphics cards
since i don't have any more.

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https://bugs.launchpad.net/bugs/1771185

Title:
  Secondary monitor not connecting in 18.04 LTS

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