The clandestine arrangement worked smoothly for years. The Israeli company shipped its internet-monitoring equipment to a distributor in Denmark. 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, said his partners in Israel and Denmark.
Israeli trade, customs and defence officials said their departments did not know that the systems for peering into internet traffic, sold under the brand name NetEnforcer, had gone to a country whose leaders have called for the destruction of Israel.
Israel's ban on trade with its enemy failed, even though a paper trail on the deals was available in Denmark.
The transactions illustrate how ineffective governments have been in blocking a global trade in new, intrusive surveillance technologies that authoritarian regimes can use as weapons for repression.
Such gear from western companies - including tools that intercept emails and text messages, record internet activity and map mobile phone locations - has been used to track and torture dissidents in countries including Iran, Bahrain, Syria and Tunisia, a Bloomberg News investigation this year showed.
It is unclear who Hossein's customers were, or how the technology may have been used in Iran.
"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," said Brett Solomon, the executive director of Access, a New York-based non-profit 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?"
But there are ways to stem the flow of such technology, which can be used as a weapon but is not 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.
Anything connected to the internet "can phone home and provide some sort of location data," said Jon Oltsik, a senior principal analyst at the Massachusetts-based Enterprise Strategy Group, a technology consulting firm.
He added that companies often stay in touch with their products to send software updates and can examine customers' internet addresses to determine where the equipment is.
The method has already proved effective, stymieing Syrian efforts to circumvent the US embargo during a crackdown that has killed more than 5,000 people.
San Diego-based Websense, a maker of internet filtering software, routinely scans the internet addresses of prospective buyers, as well as its 40,000 existing customers, to prevent its products from going to embargoed countries or falling into the wrong hands, said Michael Newman, the company's general counsel and interim chief financial officer.
In October, Websense blocked sales to two potential buyers who listed their physical addresses in Switzerland and the UAE, but who asked for the product to be downloaded to internet addresses that the company traced to Syria.
"Companies should be taking these steps," Mr Newman said. "The question is, how much are you trying to know? Or is ignorance bliss?"
Such steps could have helped Blue Coat Systems, a California-based maker of web security and filtering products.
Telecomix, a group that promotes online freedom, this year uncovered computer logs that showed the company's machines being used in Syria to filter internet sites.
Blue Coat said its products were illegally shipped to Syria by a distributor and it had been unaware they were there. Spokesman Steve Schick declined further comment on the Syria sales, citing an ongoing investigation by the department of commerce.
In this growing industry, with sales estimated at US$3-5 billion (Dh11-18bn), the potential for human rights abuse is profound.
The 10-month investigation by Bloomberg News documented the use of western surveillance technology in political crackdowns and violent repression by governments across the Middle East and North Africa.
In Bahrain, authorities used European equipment to intercept phone calls and text messages of activists, who were confronted with details of their communications while being arrested and tortured. Amid Syria's uprising, construction moved forward on a $17 million internet surveillance system built with US, French, German and Italian technology.
"Stopping this trade is a shared responsibility across government and business," said Meg Roggensack, an adjunct professor at the Georgetown University Law Centre in Washington DC, and a senior adviser to Human Rights First, a non-profit organisation based in New York and Washington. "It is extremely urgent. This is playing out in real time with real consequences for real people."
Western governments are now trying to better regulate the trade.
The shipments of internet inspection equipment from Israel to Iran illustrate the enforcement loopholes.
Allot Communications Ltd, an Israel-based firm whose stock trades on Nasdaq and the Tel Aviv Stock Exchange and which reported $57m in sales last year, sold its systems to a Randers, Denmark-based technology distributor.
Workers at that company, RanTek A/S, repackaged the gear and shipped it to Iran, according to four former employees of Allot and RanTek. The shipments were legal under Danish law.
Last week, an Israeli legislator, Nachman Shai, called for a parliamentary investigation, and the country's defence ministry said it had begun to examine the report.
"We do not authorise any sales to Iran," said Jay Kalish, the executive director of investor relations at Allot.
If its products were shipped there by RanTek, it would be a "breach of contract," he said.