On a wet evening in the Navigli, the queue outside a dark kitchen is not made of diners. It is made of riders — a dozen of them, straddling bicycles and battered scooters, thumbs hovering over the same app, waiting for the same algorithm to decide who gets the next order and what it pays. The rain is the kind that, under one reading of Italian law, entitles them to a bad-weather supplement; under another, entitles them to nothing at all, because they are not, the platforms insist, employees. Milan has spent the better part of a decade arguing about which of those two sentences is true, and the argument has produced more law, and more litigation, than anywhere else in Europe.
This is the quiet fact behind the city’s reputation. Milan is where Italy’s food-delivery economy is densest, and it is therefore where the question of what a rider actually is — self-employed contractor, semi-dependent collaborator, or simply a worker — has been fought hardest. The combatants are not the rider of folklore, riding solo into a courtroom. They are prosecutors, labour tribunals, the data-protection regulator, two confederal unions and a scattering of grassroots collectives, and four large platforms that would rather the question stayed open.
The bicycles on the Christmas tree
The organising came before the law. In Milan a grassroots collective called Deliverance Milano — a play on the English word and on liberazione — formed in 2016 and staged what is generally counted as the city’s first riders’ strike in 2017, when per-delivery rates were sliding toward three or four euros a trip. Down the motorway in Bologna, riders hung their bicycles on the Christmas tree in Piazza Maggiore during the first snowfall, a gesture that embarrassed the municipality into the negotiating room.
What came out of Bologna in May 2018 was the Carta dei diritti fondamentali del lavoro digitale nel contesto urbano, the “charter of fundamental rights of digital work in the urban context” — signed by the city, the local riders’ union, the confederal unions CGIL, CISL and UIL, and two of the platforms then operating. It was the first city-level agreement of its kind in Europe. Its central move was deceptively simple: whatever the legal label on the contract, certain protections — insurance, pay no lower than collective minimums, a supplement for night and foul-weather work — could not fall below a floor. It bound almost nobody and changed almost everything, because it gave the later legislation a vocabulary.
A word swapped in a statute
The national answer arrived as Law 128 of November 2019, the legge sui rider. It did two things. It amended Article 2 of the 2015 Jobs Act decree governing collaborazioni etero-organizzate — “hetero-organised” collaborations, work that is nominally autonomous but in practice organised by someone else — replacing the word esclusivamente (“exclusively”) with prevalentemente (“predominantly”) and dropping the requirement that the organiser dictate time and place. A single adverb widened the net. Workers caught by it are still technically self-employed, but they draw the protections of employees on pay, safety, holidays and social security.
The law’s second chapter wrote rider-specific rules directly: contracts in writing, minimum pay set by collective bargaining, supplements for night, holiday and bad-weather shifts, and mandatory accident insurance. It was a characteristically Italian compromise — it declined to call riders employees, and then handed them most of an employee’s entitlements anyway.
The algorithm in the dock
The courts went further than the statute. On the last day of 2020, the Tribunale di Bologna ruled on a complaint brought by the CGIL that Deliveroo’s ranking system — an algorithm the company had named Frank — was discriminatory. Frank scored riders on reliability and participation and quietly penalised anyone who failed to show for a booked slot, drawing no distinction between a rider who simply skipped work and one who was ill, caring for someone, or on strike. The court’s reasoning was sharp: the platform was not blind to the reasons a worker missed a shift; where it was blind, it had chosen to be. Deliveroo was ordered to pay 50,000 euros and to publish the ruling. It was the first time in Europe a court had put the organising logic of a platform, rather than just its pay, on trial.
Milan supplied the second front. In July 2021 the national data-protection authority, the Garante per la protezione dei dati personali, fined Foodinho — the Milan-based company owned by Spain’s Glovo — 2.6 million euros for the way its order-assignment algorithm processed riders’ data without adequate transparency or safeguards against discriminatory automated decisions. It was the regulator’s first ruling on riders, and it was run jointly with the Spanish authority. The lesson compounded across institutions: the same opacity that labour law treated as an employment problem, data law treated as a rights problem.
The platform is not necessarily blind to the reasons a worker skips a slot; where it is blind, it is so by deliberate choice.
Tribunale di Bologna, ruling of 31 December 2020 on the “Frank” algorithm
The €733 million sentence
Then came the document that made Milan synonymous with the fight. In February 2021, after an investigation opened in 2019 following a string of road accidents, the Procura di Milano — the city’s public prosecutor’s office, working with the labour inspectorate and the financial police — ordered the Italian arms of Deliveroo, Glovo, Just Eat and Uber Eats to regularise their riders. By the prosecutors’ count there were roughly 60,000 of them nationally, and the platforms faced proposed fines totalling around 733 million euros, levied chiefly under workplace health-and-safety law. The prosecutors’ framing was that the riders were not free agents but collaboratori coordinati e continuativi — coordinated, continuous workers — owed the safety obligations that status implies.
The figure was a proposal, not a settled penalty, and what followed was negotiation rather than mass reclassification overnight. But the number did its work. No European city had produced a single official act that put the scale of the problem — tens of thousands of riders, hundreds of millions in implied liability — on one page with a prosecutor’s signature beneath it.
The one platform that blinked
One company chose a different road. In spring 2021 Just Eat Italy signed an agreement with the transport branches of CGIL, CISL and UIL to hire its riders as direct employees under the national logistics-sector collective contract — the CCNL logistica — with a path toward thousands of staff across the country. The first cohorts came on in cities including Naples on permanent contracts, with a minimum hourly wage, guaranteed hours, paid holidays, sick leave and provided safety equipment. It remains the standout case of a major platform conceding the employee model voluntarily rather than under a court order, and rival platforms have spent the years since arguing that their lighter, freelance-led model is what most riders actually prefer.
That dispute is not settled, and Milan’s riders know it. The confederal route — NIdiL-CGIL, the branch that organises atypical and platform workers, alongside the transport unions — sits uneasily beside the grassroots collectives and rank-and-file cobas unions that called the city’s early strikes. They agree on the diagnosis and not always on the cure. A national “no delivery day” in 2020 showed they could act together; the years since have shown how hard a single bargaining table is to build when some riders want to be employees and others want to keep choosing their own hours.
What Milan exports
The European layer arrived late and owes Italy a debt it rarely acknowledges. The EU Platform Work Directive, adopted in 2024 as Directive 2024/2831, entered into force that December with a transposition deadline of December 2026. Its core mechanism — a rebuttable presumption that a platform worker is an employee where the facts show direction and control, with the burden shifting onto the platform to prove otherwise — and its limits on firing people by algorithm read like a continental generalisation of arguments first stress-tested in Bologna’s courtroom, Milan’s prosecutor’s office and the Garante’s ruling. Brussels chose, in the end, to define the triggering facts at national level rather than fix them centrally — which means Italy’s own jurisprudence will help decide what the directive means inside Italy.
Back in the Navigli, none of this has resolved the queue. The riders still wait for the algorithm; the rain still falls on a legal status nobody has fully pinned down. What Milan has built is not a clean ending but an apparatus — a charter, a statute, a body of court rulings, a regulator’s precedent, a prosecutor’s dossier and a continent’s directive — that makes the old answer, they’re just freelancers, harder to say with a straight face each year. The riders did not redraw the labour code single-handed. They made it impossible to leave alone.
Sources: Procura della Repubblica di Milano (investigation announced February 2021); Legge 128/2019 amending Art. 2 of D.Lgs. 81/2015; Tribunale di Bologna, ruling of 31 December 2020 (CGIL v. Deliveroo, “Frank” algorithm); Garante per la protezione dei dati personali, decision of July 2021 on Foodinho/Glovo (joint action with Spain’s AEPD); Carta dei diritti fondamentali del lavoro digitale nel contesto urbano (Bologna, 31 May 2018); Just Eat Italy–CGIL/CISL/UIL Trasporti agreement (2021, CCNL logistica); Directive (EU) 2024/2831 on improving working conditions in platform work; Eurofound Platform Economy Repository; reporting on Deliverance Milano and NIdiL-CGIL Milano.
