Wi-Fi Sync - devices not connecting every time???

Hello,
Should iTunes be able to automatically detect an iPhone everytime it is plugged into a power source when the Wi-Fi option is enable?
My iMac and iPhone cannot "see" each other unless I shutdown and reopen iTunes, and even that only worked three times out of eleven attempts.
Can anybody help?
Cheers.

Per my original post, it was enabled via iTunes, and it was plugged into a power source. The only time when the option is usable (not grayed out) on the iPhone is when the iPhone is plugged into the computer with iTunes running. If just plugged into any working wall outlet, with iTunes running, it does not work. The first time I tried it yesterday, it worked ONCE, and it wasn't even plugged into a power source!

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