How San Francisco's City Websites Became a Graveyard of Broken Images — and What's Being Done About It

Walk through the digital front door of San Francisco city government today and you will still find them: grey rectangles where photographs should be, broken icon links on permit pages, and staff headshots that vanished sometime around 2021 and never came back. The problem has a name inside the Department of Technology offices on Seventh Street — duplicate image replacement failure — and it traces back to a cascade of decisions made during and after the pandemic that nobody, until recently, was willing to own.

The timing matters. SF.gov, the unified city portal launched in 2019 under then-Mayor London Breed's digital services push, was built on the promise of consolidating dozens of fragmented departmental websites into one coherent, accessible experience. Three years into that project, budget pressures forced the Department of Technology to cut contractor hours. Many of the image migration workflows that were supposed to deduplicate, compress, and publish photographs from legacy systems were left half-finished. The result was a content management system carrying thousands of orphaned image references — files that existed in one database but not another, producing the blank boxes that residents now encounter when they search for, say, a Muni bus route map or a public health clinic on Potrero Avenue.

A Problem That Built Slowly, Then All at Once

The mechanics are not glamorous, but they are important. When the city consolidated its web infrastructure, individual departments — from the SF Planning Department at 49 South Van Ness Avenue to the Recreation and Park Department's administrative offices in McLaren Lodge, Golden Gate Park — were each managing their own image libraries. The migration to a centralised Drupal-based content system required those images to be re-uploaded, re-tagged, and assigned unique persistent identifiers. Duplicate files, meaning the same photograph uploaded multiple times under different filenames, were supposed to be caught by an automated deduplication process and replaced with a single canonical version.

That process broke down, according to city procurement records available through SF.gov's open data portal. A 2023 contract awarded to a Portland-based digital services firm for $340,000 addressed accessibility compliance on the city's public-facing pages but did not cover back-end image library reconciliation. The duplicate and missing image problem compounded. By late 2024, internal audits — portions of which were released under a Sunshine Ordinance request — identified more than 11,000 broken image references across city department pages, with the highest concentrations on the Department of Public Health's neighbourhood clinic directories and the Office of Economic and Workforce Development's small business resource pages.

For residents in the Tenderloin or the Excelsior who rely on mobile devices as their primary internet access point, a broken image is not a minor aesthetic irritant. It often signals to the user that the entire page is untrustworthy or out of date — a particular problem when that page is describing a naloxone distribution site or a rental assistance program with an application deadline.

What the Fix Looks Like — and How Long It Will Take

The Department of Technology issued a revised digital infrastructure roadmap in March 2026, identifying duplicate image replacement as a priority remediation item for the current fiscal year, which ends June 30, 2027. The plan calls for a combination of automated script-based deduplication and a manual audit conducted in partnership with departmental web editors across roughly 50 city agencies.

SF Digital Services, the team embedded within the Department of Technology that built and now maintains SF.gov, has been piloting the cleanup on a subset of pages since February 2026, starting with the highest-traffic sections of the Department of Building Inspection's permit portal, which logged more than 1.2 million unique visits in calendar year 2025. Early results from that pilot have not yet been published publicly.

For residents and small business owners who encounter broken images in the meantime, the practical workaround is to navigate directly to the relevant department's contact page and call or email for the resource in question. The SF Business Portal at sfbizportal.com maintains a separate, independently managed image library that has been more consistently updated. The city's 311 service line also accepts digital services complaints and routes them to the Department of Technology for logging — a paper trail that, city officials have said publicly, informs future remediation prioritisation.