This week’s Prospect Weekly Roundup sketched three stories that converge on power, choice, and the friction between public promises and private capacity: Naomi Bethune’s dispatch from Boston on Mayor Michelle Wu’s runaway re‑election—and what her dominance says about political power at the municipal level; the looming technical and civic reckoning as Microsoft ends support for Windows 10 on October 14, 2025 and forces hundreds of millions of PC users into awkward upgrade choices; and the unfolding federal government shutdown, where public messages, private maneuvers, and unilateral executive acts are shaping who pays the political and material costs. The Prospect’s short roundup framed each item as an entry point into larger dynamics of governance, technology policy, and democratic accountability.
Naomi Bethune joined David Dayen on the Prospect live show to explain why Michelle Wu’s reelection bid became effectively a coronation after a decisive primary performance. Wu’s margins in the preliminary demonstrated an unusual level of cross‑demographic support for a progressive mayor, and her challengers failed to coalesce into a credible alternative—leaving Wu unopposed heading into November. The segment tied Wu’s rise to a broad municipal policy agenda focused on housing production, transit affordability, and climate resilience.
At the same time, Microsoft’s formal notice that Windows 10 support ends on October 14, 2025 creates a real, immediate choice for users: upgrade to Windows 11 if the PC is eligible; enroll in Microsoft’s Extended Security Updates (ESU) for a limited term; buy new hardware; or keep running an unsupported OS and accept rising risk. Microsoft’s official guidance emphasizes upgrade where possible and describes ESU options, while also continuing to provide certain security intelligence updates for Microsoft Defender and Microsoft 365 apps through 2028.
Finally, the Prospect episode placed these news items against the backdrop of a federal shutdown that is producing a stark contrast between public rhetoric and private realities: elected Democrats and Republicans are advancing conflicting narratives about who is responsible, while executive actions—like freezes of federal project funding and partisan messaging routed through agency channels—are already imposing material consequences on people and communities. Polling and reporting indicate public blame is leaning toward Republicans and the president, even as the White House and allied officials publicly assign responsibility to Democrats.
Wu’s record as mayor—the city’s stated gains in housing production, fare‑free bus initiatives, stronger tenant protections, climate investments, and attempts to streamline zoning—feeds the political story. The administration points to measurable outputs: thousands of units permitted or in construction, new inclusionary zoning thresholds, and targeted federal funding allocations used to accelerate projects. These are concrete achievements that help explain why an incumbent with a bold progressive agenda can win such broad support in a large, diverse city.
Windows 11’s system requirements are materially stricter than Windows 10’s: mandatory TPM 2.0 (or firmware equivalent), UEFI/secure boot, and a CPU compatibility list that initially focused on post‑2017 processors and has been refined since. Many PCs sold in the years before 2018 lack those features or have TPM disabled by default; others run CPUs that are on Microsoft’s unsupported list. Although technical workarounds exist—registry hacks, third‑party tools, and modified installers—Microsoft’s official position is that unsupported installations are not guaranteed to receive updates and may be at elevated risk.
There are concrete mitigation strategies that companies and policymakers can adopt: targeted ESU pricing and distribution for vulnerable communities; manufacturer options to sell TPM modules or BIOS updates; public procurement exceptions that allow phased transitions; and repair‑friendly upgrade pathways that avoid wholesale disposal of functional hardware. Absent such measures, the migration will accelerate hardware turnover and exacerbate digital‑divide dynamics. Reporting and advocacy groups have already mobilized repair businesses and public interest groups to ask Microsoft for more latitude and help.
Each case raises the same practical question: Who pays when institutions change the rules? Municipal innovation can redistribute benefits to previously underserved residents but can also run into constraints when states or the federal government intervene. Technology vendors can improve security yet can also accelerate obsolescence and e‑waste. Political actors can make demands in public for purity while making private compromises—or vice versa—leaving communities to deal with the fallout.
The practical lessons are straightforward but urgent. For voters and civic organizations, Wu’s example suggests doubling down on civic capacity—insist on measurable outcomes, not just slogans. For users and IT teams, the Windows 10 deadline is not academic: inventory, back up, and pick a defensible migration path. For national leaders, the shutdown is a warning that tactics which weaponize administrative levers will leave constituencies worse off and erode democratic legitimacy.
The coming weeks will test how these institutions absorb stress: whether municipal governments maintain momentum, whether Microsoft and the broader tech ecosystem provide humane transition options, and whether federal politics can return to a bargaining posture that preserves essential services rather than treats them as instruments of leverage. The answer will shape not only who wins the next election, but how resilient daily life will be for millions of people who use a mayor’s services, a company’s operating system, and a federal safety net.
Source: The American Prospect The Prospect Weekly Roundup: Mamdani Before Mamdani
Naomi Bethune joined David Dayen on the Prospect live show to explain why Michelle Wu’s reelection bid became effectively a coronation after a decisive primary performance. Wu’s margins in the preliminary demonstrated an unusual level of cross‑demographic support for a progressive mayor, and her challengers failed to coalesce into a credible alternative—leaving Wu unopposed heading into November. The segment tied Wu’s rise to a broad municipal policy agenda focused on housing production, transit affordability, and climate resilience. At the same time, Microsoft’s formal notice that Windows 10 support ends on October 14, 2025 creates a real, immediate choice for users: upgrade to Windows 11 if the PC is eligible; enroll in Microsoft’s Extended Security Updates (ESU) for a limited term; buy new hardware; or keep running an unsupported OS and accept rising risk. Microsoft’s official guidance emphasizes upgrade where possible and describes ESU options, while also continuing to provide certain security intelligence updates for Microsoft Defender and Microsoft 365 apps through 2028.
Finally, the Prospect episode placed these news items against the backdrop of a federal shutdown that is producing a stark contrast between public rhetoric and private realities: elected Democrats and Republicans are advancing conflicting narratives about who is responsible, while executive actions—like freezes of federal project funding and partisan messaging routed through agency channels—are already imposing material consequences on people and communities. Polling and reporting indicate public blame is leaning toward Republicans and the president, even as the White House and allied officials publicly assign responsibility to Democrats.
Michelle Wu: A new model of municipal power
From campaign to governing mandate
Michelle Wu’s preliminary victory and the subsequent collapse of challengers into withdrawal or failure to qualify made the November ballot a formality: she will run unopposed, a rare position for a major‑city incumbent. Local reporting and polling showed margins that made this not just a win but a mandate—72 percent in the preliminary and polls indicating broad support across racial and neighborhood lines. Observers interpreted that margin as validation for an agenda that blends progressive policy experimentation with institutional reforms aimed at faster delivery.Wu’s record as mayor—the city’s stated gains in housing production, fare‑free bus initiatives, stronger tenant protections, climate investments, and attempts to streamline zoning—feeds the political story. The administration points to measurable outputs: thousands of units permitted or in construction, new inclusionary zoning thresholds, and targeted federal funding allocations used to accelerate projects. These are concrete achievements that help explain why an incumbent with a bold progressive agenda can win such broad support in a large, diverse city.
Why the form of power matters
Wu’s popularity is notable because it signals that a mayor who openly embraces progressive policy levers can both govern and win electoral consent at scale. That matters for two reasons. First, city governments control the levers that most directly impact residents’ daily lives—housing, transit, permitting, local economic development—so successful municipal innovation can produce real gains even when federal politics is gridlocked. Second, Wu’s position as a progressive Asian American in a historically white political class challenges assumptions about who can be a mainstream executive in large U.S. cities. The political effect is not merely symbolic; it reshapes who organizes for power in municipal politics and how coalition building happens across neighborhoods and constituencies.Strengths and limits
- Strengths:
- Delivery orientation. Wu’s administration has emphasized measurable outputs—units produced, funds allocated, pilot programs launched—helping translate policy talk into voter‑visible results.
- Coalition breadth. Polling showed expanded support across demographic groups, which reduces vulnerability to narrow coalitions and strengthens governing capacity.
- Limits and risks:
- Uncontested reelection compresses accountability. Running unopposed reduces competitive incentives for rigorous scrutiny; civic oversight and adversarial debate are essential guardrails even for effective incumbents.
- Policy trade‑offs. Aggressive housing tools (rezoning, inclusionary policy, linkage fees) can stimulate supply but provoke legal and political pushback from real estate interests and state law constraints.
- Federal friction. Wu’s sanctuary‑city posture and clashes with the federal executive branch demonstrate how local policy can be legally and politically contested, raising litigation and enforcement risks.
Windows 10 end of support: technical facts and human consequences
The technical bottom line
Microsoft’s announcement is simple and absolute: Windows 10 will no longer receive free software updates, security patches, or technical support after October 14, 2025. For consumers and organizations this means no more routine security fixes from Windows Update, and continued exposure to newly discovered vulnerabilities unless they migrate. Microsoft has published the guidance and detailed an ESU program (Extended Security Updates) to provide a limited bridge; it has also said certain services—security intelligence updates for Microsoft Defender and Microsoft 365 Apps—will continue through 2028.Windows 11’s system requirements are materially stricter than Windows 10’s: mandatory TPM 2.0 (or firmware equivalent), UEFI/secure boot, and a CPU compatibility list that initially focused on post‑2017 processors and has been refined since. Many PCs sold in the years before 2018 lack those features or have TPM disabled by default; others run CPUs that are on Microsoft’s unsupported list. Although technical workarounds exist—registry hacks, third‑party tools, and modified installers—Microsoft’s official position is that unsupported installations are not guaranteed to receive updates and may be at elevated risk.
How many people are affected?
Estimates vary, and any single number should be treated cautiously. Industry trackers—StatCounter and other market analysts—show that a large share of desktop Windows usage still ran Windows 10 through 2024 and into 2025, with Windows 11 gaining share rapidly as the deadline approached. Journalistic estimates and reporting have put the number of Windows 10 PCs in the high‑hundreds of millions—figures like 400 million to 900 million appear in multiple outlets, but those are dependent on different counting methods (active installs vs. devices ever activated), and should be treated as rough orders of magnitude rather than precise counts. The practical point is clear: this is not a small niche problem; this is a global user base that includes consumers, small businesses, schools, and government agencies.Options for users and administrators
When an OS reaches end of support, the realistic options converge to a short list—each with costs and trade‑offs:- Upgrade to Windows 11 (free if your device is eligible). Check eligibility via Microsoft’s PC Health Check or Settings. This preserves support and security but may require BIOS/firmware changes (enable TPM) or hardware replacements.
- Enroll eligible devices in Microsoft’s ESU program for a temporary bridge (consumer ESU options include a free route tied to Microsoft accounts or a paid one‑time purchase; enterprise ESU terms differ by contract). ESU buys time but is not a permanent solution.
- Replace the device with new hardware built for Windows 11 (upfront cost; environmental and e‑waste implications).
- Switch to an alternative OS (Linux distributions, ChromeOS Flex) where feasible—this can work for many tasks but may create application and support friction.
- Continue using Windows 10 unsupported: possible in the short term but progressively risky as threat actors discover and weaponize vulnerabilities. Security posture will depend on mitigating controls (third‑party antivirus, network segmentation, offline operation).
Planned obsolescence or necessary evolution?
The phrase planned obsolescence is emotionally resonant and politically potent. Technically, Microsoft’s move is driven by security architecture choices: Windows 11 embeds hardware‑level protections (TPM, virtualization‑based security) designed to raise the baseline for platform defenses. Those design choices are defensible on security grounds. But the decision also forces a mass upgrade cycle whose economic and environmental costs fall unevenly on lower‑income users, small repair shops, public institutions, and regions with constrained budgets. That tension—between security progress and distributive burden—is the heart of the planned‑obsolescence critique.There are concrete mitigation strategies that companies and policymakers can adopt: targeted ESU pricing and distribution for vulnerable communities; manufacturer options to sell TPM modules or BIOS updates; public procurement exceptions that allow phased transitions; and repair‑friendly upgrade pathways that avoid wholesale disposal of functional hardware. Absent such measures, the migration will accelerate hardware turnover and exacerbate digital‑divide dynamics. Reporting and advocacy groups have already mobilized repair businesses and public interest groups to ask Microsoft for more latitude and help.
Step‑by‑step preparation checklist (for consumers and small orgs)
- Run Microsoft’s PC Health Check to test Windows 11 eligibility; check for firmware TPM that can be enabled in UEFI.
- Back up important files to cloud services or external drives—migrations fail when data aren’t preserved.
- If eligible, schedule the upgrade and test critical applications for compatibility.
- If ineligible, evaluate ESU enrollment or plan a hardware refresh—get quotes from reputable local repair shops.
- Explore Linux or ChromeOS Flex as a fallback for machines used mainly for web, email, and documents.
- For businesses and public entities: audit hardware inventories, prioritize mission‑critical endpoints for early upgrade, and budget for phased capital expenditures.
The shutdown: messaging, unilateral acts, and real damage
Public narrative vs private realities
The Prospect flagged a consistent pattern: public messaging is often simplified to blame the other party while behind the scenes negotiators and officials run through more complicated tradeoffs. Current polling shows that a plurality of Americans blame the president and Republican leaders for the shutdown, even as administration messaging assigns culpability to Democrats. Those attribution patterns matter politically—they influence public sympathy, midterm mobilization, and the acceptability of unilateral executive responses that reallocate or freeze resources.Unilateral executive moves have immediate effects
While the debate centers on congressional fault lines, executive action is already doing material work on the ground. Reports documented administration freezes of billions of dollars in local transit and infrastructure funding, decisions that can delay construction, halt reimbursements, and raise costs for projects already planned and funded. Freezing funds becomes an instrument of political pressure that has geographically dispersed winners and losers—often hitting Democratic‑led localities and vulnerable communities hardest. At the same time, agency communications during the shutdown—templates or altered out‑of‑office messages blaming Democrats—raise legal and ethical concerns about partisan use of government channels.Political and policy consequences
- Short‑term harm. Project delays, furloughed contract workers, disrupted services (from national parks to grant reimbursements), and anxiety for families that depend on timing‑sensitive benefits.
- Longer‑term damage. Cost inflation on delayed infrastructure projects, weakened trust in federal reliability, and the politicization of program administration (when officials weaponize funding decisions).
- Electoral effects. Public attribution of blame will shape the political calculus for coming elections; polling suggests Republicans are more likely to be held responsible in this moment.
How these threads connect: governance, technical debt, and accountability
There is a throughline from Boston’s municipal politics to Microsoft’s product lifecycle to the federal shutdown: the structure of power determines who absorbs the costs of transition. A city mayor who can credibly deliver services and production—Wu’s defining trait in Boston’s politics—gains political capital. A dominant software vendor that chooses to raise the baseline for platform security imposes costs across civil society that will be distributed unevenly. And a federal executive willing to wield administrative levers during a funding impasse reshapes how political choices translate into material outcomes.Each case raises the same practical question: Who pays when institutions change the rules? Municipal innovation can redistribute benefits to previously underserved residents but can also run into constraints when states or the federal government intervene. Technology vendors can improve security yet can also accelerate obsolescence and e‑waste. Political actors can make demands in public for purity while making private compromises—or vice versa—leaving communities to deal with the fallout.
Recommendations and red flags
For municipal leaders and advocates
- Use the political capital of a mandate to institutionalize transparency: publish performance metrics, calibration plans, and oversight reviews so that a lack of electoral competition does not become a governance vacancy.
- Negotiate state and federal partnerships proactively to insulate local projects from partisan freezes; have contingency funding or bridge instruments for critical infrastructure.
For IT managers, small business owners, and consumers
- Treat October 14, 2025 as a hard deadline for planning: inventory devices, test upgrades, and budget for ESU or hardware replacement. Official Microsoft guidance and the built‑in PC Health Check are the first stops.
- Consider Linux/ChromeOS Flex where mission needs allow; this reduces vendor lock‑in risk and can extend usable hardware life.
For federal and corporate policymakers
- Design ESU or migration subsidy programs targeted at schools, clinics, and community organizations to prevent the transition from worsening inequality.
- Encourage repair‑market supports and offer low‑cost TPM modules or BIOS updates where feasible.
Red flags to watch
- Overreliance on workarounds. Unsupported installations of Windows 11 or continued use of Windows 10 without ESU risk brittle security and noncompliant environments.
- Partisan administrative weaponization. Freezing projects selectively during a shutdown sets a precedent that turns public goods into political levers; litigation and long delays often follow.
- Democratic erosion through uncontested power. Uncontested races concentrate authority; even effective governance benefits from routine electoral contestation and institutional checks.
Conclusion
The Prospect’s roundup packaged three seemingly disparate stories into a single argument about the mechanics of power in 2025: mayors who deliver locally can reshape politics even when national discourse is poisonous; platform decisions about security and support can functionally rewrite the life cycle of billions of devices and redistribute costs across households and institutions; and a shutdown exposes the gap between campaign rhetoric and administrative reality, where unilateral acts inflict tangible harm while partisan narratives compete for credit and blame. Each story is, at base, about choices—technical and political—and who gets to make them.The practical lessons are straightforward but urgent. For voters and civic organizations, Wu’s example suggests doubling down on civic capacity—insist on measurable outcomes, not just slogans. For users and IT teams, the Windows 10 deadline is not academic: inventory, back up, and pick a defensible migration path. For national leaders, the shutdown is a warning that tactics which weaponize administrative levers will leave constituencies worse off and erode democratic legitimacy.
The coming weeks will test how these institutions absorb stress: whether municipal governments maintain momentum, whether Microsoft and the broader tech ecosystem provide humane transition options, and whether federal politics can return to a bargaining posture that preserves essential services rather than treats them as instruments of leverage. The answer will shape not only who wins the next election, but how resilient daily life will be for millions of people who use a mayor’s services, a company’s operating system, and a federal safety net.
Source: The American Prospect The Prospect Weekly Roundup: Mamdani Before Mamdani