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The clandestine arrangement worked smoothly for years. The Israeli company shipped its Internet- monitoring equipment to a distributor inDenmark. Once there, workers stripped away the packaging and removed the labels.

Then they sent it to a man named “Hossein” in Iran, an amiable technology distributor known to them only by his first name and impeccable English, say his partners in Israel and Denmark.

“The fact that the most murderous regimes are using Western technologies for surveillance highlights the fact that the current framework for controlling this dirty trade is not working,” says Brett Solomon, executive director of Access, a New York-based nonprofit that promotes online freedom. “How long are the innocent people of Syria and Iran to wait before Congress and the EU turn words into law?”

Yet there are ways to stem the flow of such technology, which can be used as a weapon but isn’t regulated like one. Many companies selling surveillance equipment that connects to the Internet have the ability to monitor their own customers, and governments could require them to do so while tightening export laws.