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If you have sent a check that will not route in your normal transit, its possible that the Fed debited the banks account and returned the item (or lost it) in such a manner that operations personel may not have known what to do with it. Have you checked the Suspense Account lately.
You can sign up through Fed to clear foreign items; we did this a couple of months ago by contacting our FRB acct rep. Of course they charge out the wazoo for it (per item and per letter cost) but we simply pass the cost onto our customers. We get a notice from Fed that we have deposited a foreign item, and if there is a difference in the exchange rate we get charged/credited for that and we of course debit/credit our customer for that also. The Fed notificaiton is the only way we would know if we deposited a foreign item and can look it up in the myriad of reports we have to see which customer deposited the item. We have a lot of Canadian tourists in our area and we were almost forced into providing this service for whitewater rafting companies.