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When the iphone is out of cell signal for a period of time (overnight),  the iphone appears to poll to check for a new signal from the cell at longer and longer intervals. This is good in general, as constantly polling the cell tower would very quickly deplete the battery.
However, when moving back into an area with cell coverage (which in my case just means moving outside), the amount of time before the phone re-connects can be very long.   The exception to this is that if the main button is pressed to wake the phone up, the phone immediately performs a cell tower check and reconnects.

If you get into a car however without pressing the button, you can be driving around with no phone signal for quite awhile. This is even the case if you have the phone paired to the car via bluetooth.

In this instance, the pairing is completed, and the phone continues to not check the cell tower for quite sometime – Unless the button is pressed as you approach the car (which does resolve the problem, however most inconvenient).

So until Apple make the cell search start when the bluetooth pairs (which would probably be the easiest fix) dont forget to wake up the iphone before setting off.

This happens everyday to me , i must try and remember to press that button.

[Update 22nd September 2009]

So, 10 months on, Version 3 of the O.S. and guess what, still the same problem, i love the iPhone, but need the connectivity reliability of a main stream brand. After all, this is supposed to be a mobile telephone first and foremost