Imac not recognizing 2nd monitor

On cold startup, why do I always need to unplug and replug thunderbolt mini display to vga adapter for imac to see second monitor ?
Once I do this, the 2nd monitor is recognized. If I restart, 2nd monitor is recognized.
thanks.. I am worried that the port will be compromised with all the unplug/replugs.
Btw... the "detect displays" function doesn't resolve this issue.
thanks for any help!
~john theaker
windsor ontario canada
iMac 2.8gz quad core 17
Samsung monitor
mini

Hi John,
I really have no idea, but as a test, hold alt key at cold startup, let it set on that screen for maybe a minute or two, then click the startup volume or hit enter... any change?
Also, if you log out & back in does it show up?

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