SPOT will not send an OK message until it has a GPS fix. Like most GPS units, it can take several minutes to get a fix, especially if the unit has been off for awhile or has been moved a large distance. Once it gets the fix, it sends three messages over the course of several minutes. In my experience, SPOT gets a fix about as well as a typical 12-channel non-SIRF Garmin (e.g. Foretrex/eTrex 101). If the lights blink out of phase, you know it didn't get a fix, and thus no OK message was sent.
For me, the OK button works with very high reliability, but I generally use it when stopping for a lunch/snack break, at camp, or while otherwise stationary at a location where I'd normally expect to get GPS coverage–open sky, low horizon, etc. I also leave it laying out for ~15 minutes after activated to provide ample time to get a fix and send the messages. This usage pattern may not be suitable for all SPOT users, but for my purposes (providing status updates to friends/relatives), it works very well. (I have not used or tested the tracking feature, but expect it would not work as reliably, just as a stationary GPS fix is almost always better than an on-the-run tracking fix.)
The Help and 911 buttons *will* transmit without waiting for a fix. I'd expect that SPOT will continue to try to get a fix while repeating these messages.