This is not a poblem of an adapter, but of the rather byzantine design of the DVI
interface: DVI
is one of the very few cables, that are able to carry an analog signal and a digital signal on the same plug.
It is perfectly legitimate for a DVI device, cable or adapter to support only the former or only the latter.
With your first example, you started with HDMI
- a pure digital signal. The adapter converted it to a DVI
plug just fine, but of course it only used the pins for the digital signal, leaving the analog ones unused. The next adapter was intended to convert it to VGA
, which is a purely analog signal. The adapter would use only the analaog pins of DVI
(where there is no signal) and ignore the digital ones (where there would be one available) - this ofcourse didn't work
In your second example, you start with micro-HDMI
(digital), convert to HDMI
(digital again) and finally to DVI - this will work, if the Monitor uses the digital pins of the DVI plug, not only the analog ones.
All monitors I ever saw, that had a DVI plug used these digital pins, so expect it to work fine.