diff --git a/src/__tests__/publisher/classStyleInjector.test.ts b/src/__tests__/publisher/classStyleInjector.test.ts
index 4b5f5efc2..f7620ee81 100644
--- a/src/__tests__/publisher/classStyleInjector.test.ts
+++ b/src/__tests__/publisher/classStyleInjector.test.ts
@@ -662,6 +662,84 @@ describe('generateClassCSS', () => {
     expect(desktopIdx).toBeGreaterThan(tabletIdx)
   })
 
+  it('keeps min-width contexts narrowest-first when a max-width context sits between them', () => {
+    // Regression: width order is only defined between two contexts of the same
+    // query kind, so ordering used to fall back to registry index for a
+    // min-vs-max pair. That made the comparison non-transitive — the two
+    // min-width contexts below are never compared to each other, and the
+    // 1024px block was emitted before the 768px one. Both match above 1024px,
+    // specificity is equal, so the 768px block won and mobile-first inverted.
+    const breakpoints = [
+      { id: 'desktop', width: 1024, mediaQuery: '(min-width: 1024px)' },
+      { id: 'mobile', width: 900, mediaQuery: '(max-width: 900px)' },
+      { id: 'tablet', width: 768, mediaQuery: '(min-width: 768px)' },
+    ]
+    const classes = {
+      hero: makeClass('hero', { color: 'rgb(1, 2, 3)' }, {
+        desktop: { color: 'rgb(13, 14, 15)' },
+        mobile: { color: 'rgb(7, 8, 9)' },
+        tablet: { color: 'rgb(10, 11, 12)' },
+      }),
+    }
+    const css = generateClassCSS(classes, breakpoints)
+    const tabletIdx = css.indexOf('@media (min-width: 768px)')
+    const desktopIdx = css.indexOf('@media (min-width: 1024px)')
+    expect(tabletIdx).toBeGreaterThanOrEqual(0)
+    expect(desktopIdx).toBeGreaterThan(tabletIdx)
+  })
+
+  it('keeps max-width contexts widest-first when a min-width context sits between them', () => {
+    const breakpoints = [
+      { id: 'narrow', width: 600, mediaQuery: '(max-width: 600px)' },
+      { id: 'desktop', width: 1024, mediaQuery: '(min-width: 1024px)' },
+      { id: 'wide', width: 900, mediaQuery: '(max-width: 900px)' },
+    ]
+    const classes = {
+      hero: makeClass('hero', { color: 'rgb(1, 2, 3)' }, {
+        narrow: { color: 'rgb(4, 5, 6)' },
+        desktop: { color: 'rgb(13, 14, 15)' },
+        wide: { color: 'rgb(7, 8, 9)' },
+      }),
+    }
+    const css = generateClassCSS(classes, breakpoints)
+    const wideIdx = css.indexOf('@media (max-width: 900px)')
+    const narrowIdx = css.indexOf('@media (max-width: 600px)')
+    expect(wideIdx).toBeGreaterThanOrEqual(0)
+    expect(narrowIdx).toBeGreaterThan(wideIdx)
+  })
+
+  it('orders viewport contexts by the registry, not by contextStyles key order', () => {
+    // `contextStyles` is keyed in authoring order, which is not registry order.
+    // Emission must not depend on it: the same registry and the same overrides
+    // produce the same CSS whichever order the keys were written in.
+    const breakpoints = [
+      { id: 'desktop', width: 1024, mediaQuery: '(min-width: 1024px)' },
+      { id: 'mid', width: 1023, mediaQuery: '(max-width: 1023px)' },
+      { id: 'tablet', width: 768, mediaQuery: '(min-width: 768px)' },
+    ]
+    const overrides = {
+      desktop: { color: 'rgb(13, 14, 15)' },
+      mid: { color: 'rgb(7, 8, 9)' },
+      tablet: { color: 'rgb(10, 11, 12)' },
+    }
+    const authoredOneWay = generateClassCSS(
+      { hero: makeClass('hero', { color: 'rgb(1, 2, 3)' }, overrides) },
+      breakpoints,
+    )
+    const authoredAnother = generateClassCSS(
+      { hero: makeClass('hero', { color: 'rgb(1, 2, 3)' }, {
+        tablet: overrides.tablet,
+        desktop: overrides.desktop,
+        mid: overrides.mid,
+      }) },
+      breakpoints,
+    )
+    expect(authoredAnother).toBe(authoredOneWay)
+    expect(authoredOneWay.indexOf('@media (min-width: 1024px)')).toBeGreaterThan(
+      authoredOneWay.indexOf('@media (min-width: 768px)'),
+    )
+  })
+
   it('rewrites class background images with responsive image-set candidates', () => {
     const classes = {
       hero: makeClass('hero', { backgroundImage: "url('/uploads/hero.png')" }),
diff --git a/src/core/publisher/classCss.ts b/src/core/publisher/classCss.ts
index 87321ea25..6c2bbaa7e 100644
--- a/src/core/publisher/classCss.ts
+++ b/src/core/publisher/classCss.ts
@@ -270,6 +270,11 @@ export function bagToReactStyle(
  * narrowest matching query wins. Pure min-width contexts emit narrowest first
  * so the widest matching query wins. Mixed/custom viewport queries keep the
  * user's registry order.
+ *
+ * Those two width orderings are *within* a query kind: a registry holding both
+ * `min-width` and `max-width` contexts keeps the two groups in registry order
+ * and sorts each group by width in its own slots. See
+ * `sortViewportContextCascade`.
  */
 export interface ViewportContext {
   id: string
@@ -296,15 +301,49 @@ function viewportQuerySort(breakpoint: ViewportContext): ViewportQuerySort {
   return { kind: 'other', width: breakpoint.width }
 }
 
-export function compareViewportContextCascade(
-  a: { breakpoint: ViewportContext; index: number },
-  b: { breakpoint: ViewportContext; index: number },
-): number {
-  const aQuery = viewportQuerySort(a.breakpoint)
-  const bQuery = viewportQuerySort(b.breakpoint)
-  if (aQuery.kind === 'max' && bQuery.kind === 'max') return bQuery.width - aQuery.width
-  if (aQuery.kind === 'min' && bQuery.kind === 'min') return aQuery.width - bQuery.width
-  return a.index - b.index
+/**
+ * Order viewport contexts for emission.
+ *
+ * This cannot be a plain `Array.prototype.sort` comparator. Width order is only
+ * meaningful between two contexts of the same query kind — comparing a
+ * `min-width` against a `max-width` has no answer, and falling back to registry
+ * index for those pairs makes the comparator non-transitive: with
+ * `[min-width: 1024px, max-width: 900px, min-width: 768px]` the two min-width
+ * contexts never get compared to each other, so the 1024px block is emitted
+ * before the 768px one and wins the equal-specificity tie at every viewport
+ * above 1024px. Mobile-first CSS silently inverts.
+ *
+ * Instead, partition by kind over registry order and sort each kind group
+ * within the slots that group already occupies. Cross-kind order stays registry
+ * order, `min`/`max` groups get their width order regardless of how the kinds
+ * interleave, and `other` (mixed or non-pixel queries, where width order is not
+ * defined) is never reordered.
+ */
+export function sortViewportContextCascade<T extends { breakpoint: ViewportContext; index: number }>(
+  entries: readonly T[],
+): T[] {
+  // Registry order first, so the result never depends on the caller's array
+  // order (`contextStyles` key order is authoring order, not registry order).
+  const ordered = entries.slice().sort((a, b) => a.index - b.index)
+
+  for (const kind of ['min', 'max'] as const) {
+    const slots: number[] = []
+    for (let i = 0; i < ordered.length; i++) {
+      if (viewportQuerySort(ordered[i].breakpoint).kind === kind) slots.push(i)
+    }
+    if (slots.length < 2) continue
+
+    const group = slots.map((slot) => ordered[slot])
+    group.sort((a, b) => {
+      const aWidth = viewportQuerySort(a.breakpoint).width
+      const bWidth = viewportQuerySort(b.breakpoint).width
+      if (aWidth !== bWidth) return kind === 'min' ? aWidth - bWidth : bWidth - aWidth
+      return a.index - b.index
+    })
+    slots.forEach((slot, i) => { ordered[slot] = group[i] })
+  }
+
+  return ordered
 }
 
 /**
@@ -318,7 +357,7 @@ export function compareViewportContextCascade(
  * between what the editor shows and what a publish ships.
  *
  * Cascade order (precedence Q-A): base → custom conditions (registry order) →
- * viewport @media contexts (see `compareViewportContextCascade`). Context keys
+ * viewport @media contexts (see `sortViewportContextCascade`). Context keys
  * matching neither registry are skipped (orphaned overrides).
  */
 export interface StyleRuleDeclarationLayers {
@@ -390,8 +429,7 @@ export function createStyleRuleCssEmitter(
       blocks.push(`${prelude} {\n  ${selector} {\n${decls}\n  }\n}`)
     }
 
-    bpEntries.sort(compareViewportContextCascade)
-    for (const { contextId, bag, breakpoint } of bpEntries) {
+    for (const { contextId, bag, breakpoint } of sortViewportContextCascade(bpEntries)) {
       const decls = bagToCSS(bag, options, layers.contextStylePriorities?.[contextId])
       if (!decls) continue
       const prelude = conditionPrelude({ kind: 'media', query: breakpointMediaQuery(breakpoint) })
diff --git a/src/core/publisher/sizesResolver.ts b/src/core/publisher/sizesResolver.ts
index 5856b2482..5c1cfd412 100644
--- a/src/core/publisher/sizesResolver.ts
+++ b/src/core/publisher/sizesResolver.ts
@@ -62,7 +62,7 @@
  * tier — the caller falls back to `100vw`.
  */
 import { breakpointMediaQuery, type Page, type PageNode, type SiteDocument } from '@core/page-tree'
-import { compareViewportContextCascade } from './classCss'
+import { sortViewportContextCascade } from './classCss'
 
 // ---------------------------------------------------------------------------
 // Linear width candidates
@@ -491,10 +491,9 @@ export function resolveAutoSizes(
 
   // Viewport tiers in `sizes` first-match order — the reverse of the CSS
   // cascade, so the candidate that would win in CSS is hit first.
-  const tiers = site.breakpoints
-    .map((breakpoint, index) => ({ breakpoint, index }))
-    .sort(compareViewportContextCascade)
-    .reverse()
+  const tiers = sortViewportContextCascade(
+    site.breakpoints.map((breakpoint, index) => ({ breakpoint, index })),
+  ).reverse()
 
   const entries: Array<{ query: string | null; value: string }> = []
   for (const { breakpoint } of tiers) {