We recently rolled out two changes to the Bitcoin block acceptance rules (BIP16 and BIP30); this document records the lessons learned and makes recommendations for handling future blockchain rule changes.
Note: there are "soft" rule changes and "hard" rule changes. "Soft" changes tighten up the rules-- old software will accept all the blocks and transactions created by new software, but the opposite may not be true. "Soft" changes do not require the entire network of miners and merchants and users to upgrade or be left behind.
"Hard" changes modify the rules in a way that old, un-upgraded software consider illegal. At this point it is much, much more difficult (some might say impossible) to roll out "hard" changes, because they require every miner and merchant and user to upgrade.