I know that this does happen. The SEC says there are some settlement failures in 4% of all stocks traded. In my view, not a very big deal.
In the case of Paid, Inc., it took some holders weeks and months to get certs. After many delays, several holders claimed that the brokerages finally admitted that some transactions from 2 and 3 months prior had not been settled and that's why certs were not sent.
I thought Schwab's letter to the SEC was interesting. It suggests that these settlement failures are largely due to simple carelessness. Makes sense to me.
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