After I managed to solve my issues with the HDMI - VGA converter by reinstalling Ubuntu, I was wondering why Ubuntu keeps my resolution settings in some cases and loses them in others. I've written a small batch script that executes the following:

xrandr --newmode "1440x900_60.00" 106.50 1440 1528 1672 1904 900 903 909 934 -hsync +vsync xrandr --addmode HDMI1 1440x900_60.00

This adds 1440x900 to my HDMI display port, allowing me the correct (highest) resolution used by the external monitor. Some days I shutdown, and start up again, and the settings remains in tact, but then... sometimes I merely reboot and I have to re-run the script.

Just curious... it's not too much hassle to run the xrandr commands, but would be nice if I didn't have to