Is this the type of dendrobium that has phal-like spikes? If so, they often bloom three times a year, for two and a half months each time. They also re-bloom off old canes. Mine hate being re-potted and, after being knocked over three times by my kids and dogs two years ago, my nice noID nearly died but is now recovering nicely. So, that is definitely something to avoid. I grow mine in lava rock and a basket pot (so no need to worry about decaying medium). It is currently in a West window but prefers a South-facing window and as much light as a cattleya. They prefer 60'F and up, temp-wise, and do well in a fast-draining medium. Hope this helps.
If the blooms are dropping prematurely, it might be because of some change in the environment or a problem with the roots. If you don't know how long it has been in bloom, then you are likely right that the time has come....
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