diff --git a/news/changelog-1.10.md b/news/changelog-1.10.md
index fb34c2e35bc..5d88aa130f3 100644
--- a/news/changelog-1.10.md
+++ b/news/changelog-1.10.md
@@ -32,6 +32,7 @@ All changes included in 1.10:
 ### Websites
 
 - ([#13565](https://github.com/quarto-dev/quarto-cli/issues/13565), [#14353](https://github.com/quarto-dev/quarto-cli/issues/14353)): Fix sidebar logo not appearing on secondary sidebars in multi-sidebar website layouts.
+- ([#14493](https://github.com/quarto-dev/quarto-cli/issues/14493)): Fix category links on a post going to the wrong listing when the post appears in multiple listings.
 
 ## Commands
 
diff --git a/src/resources/formats/html/quarto.js b/src/resources/formats/html/quarto.js
index ee807684be1..87af95342c7 100644
--- a/src/resources/formats/html/quarto.js
+++ b/src/resources/formats/html/quarto.js
@@ -311,22 +311,22 @@ window.document.addEventListener("DOMContentLoaded", function (_event) {
   }
 
   const findNearestParentListing = (href, listingHrefs) => {
-    if (!href || !listingHrefs) {
+    if (!href || !listingHrefs?.length) {
       return undefined;
     }
-    // Look up the tree for a nearby linting and use that if we find one
-    const relativeParts = href.substring(1).split("/");
-    while (relativeParts.length > 0) {
-      const path = relativeParts.join("/");
-      for (const listingHref of listingHrefs) {
-        if (listingHref.startsWith(path)) {
-          return listingHref;
-        }
+    // Match listings whose directory is a prefix of the post directory at a
+    // path-segment boundary, then keep the deepest one.
+    const postDir = href.replace(/[^/]+$/, "");
+    let best;
+    let bestLen = -1;
+    for (const listingHref of listingHrefs) {
+      const listingDir = listingHref.replace(/[^/]+$/, "");
+      if (postDir.startsWith(listingDir) && listingDir.length > bestLen) {
+        best = listingHref;
+        bestLen = listingDir.length;
       }
-      relativeParts.pop();
     }
-
-    return undefined;
+    return best;
   };
 
   const manageSidebarVisiblity = (el, placeholderDescriptor) => {
diff --git a/tests/docs/playwright/blog/multi-listing-blog/.gitignore b/tests/docs/playwright/blog/multi-listing-blog/.gitignore
new file mode 100644
index 00000000000..47c274c17b6
--- /dev/null
+++ b/tests/docs/playwright/blog/multi-listing-blog/.gitignore
@@ -0,0 +1,2 @@
+/.quarto/
+/_site/
diff --git a/tests/docs/playwright/blog/multi-listing-blog/_quarto.yml b/tests/docs/playwright/blog/multi-listing-blog/_quarto.yml
new file mode 100644
index 00000000000..1bbaf455dcc
--- /dev/null
+++ b/tests/docs/playwright/blog/multi-listing-blog/_quarto.yml
@@ -0,0 +1,13 @@
+project:
+  type: website
+
+website:
+  title: "Multi-listing blog"
+  navbar:
+    left:
+      - href: index.qmd
+        text: Home
+      - href: blog/index.qmd
+        text: Blog
+
+format: html
diff --git a/tests/docs/playwright/blog/multi-listing-blog/blog/index.qmd b/tests/docs/playwright/blog/multi-listing-blog/blog/index.qmd
new file mode 100644
index 00000000000..01edff182ba
--- /dev/null
+++ b/tests/docs/playwright/blog/multi-listing-blog/blog/index.qmd
@@ -0,0 +1,8 @@
+---
+title: "Blog"
+listing:
+  contents: "*/index.qmd"
+  type: default
+  sort: "date desc"
+  categories: true
+---
diff --git a/tests/docs/playwright/blog/multi-listing-blog/blog/post-one/index.qmd b/tests/docs/playwright/blog/multi-listing-blog/blog/post-one/index.qmd
new file mode 100644
index 00000000000..1e2f336f5d9
--- /dev/null
+++ b/tests/docs/playwright/blog/multi-listing-blog/blog/post-one/index.qmd
@@ -0,0 +1,9 @@
+---
+title: "Post one"
+date: "2026-01-02"
+categories:
+  - alpha
+  - beta
+---
+
+Body of post one.
diff --git a/tests/docs/playwright/blog/multi-listing-blog/blog/post-two/index.qmd b/tests/docs/playwright/blog/multi-listing-blog/blog/post-two/index.qmd
new file mode 100644
index 00000000000..e4e164d71ea
--- /dev/null
+++ b/tests/docs/playwright/blog/multi-listing-blog/blog/post-two/index.qmd
@@ -0,0 +1,8 @@
+---
+title: "Post two"
+date: "2026-01-01"
+categories:
+  - alpha
+---
+
+Body of post two.
diff --git a/tests/docs/playwright/blog/multi-listing-blog/index.qmd b/tests/docs/playwright/blog/multi-listing-blog/index.qmd
new file mode 100644
index 00000000000..02a7b42c199
--- /dev/null
+++ b/tests/docs/playwright/blog/multi-listing-blog/index.qmd
@@ -0,0 +1,15 @@
+---
+title: "Home"
+listing:
+  id: latest
+  contents: blog/*/index.qmd
+  type: default
+  sort: "date desc"
+  filter-ui: false
+  sort-ui: false
+---
+
+Site root with a listing of latest posts.
+
+::: {#latest}
+:::
diff --git a/tests/integration/playwright/tests/blog-multi-listing.spec.ts b/tests/integration/playwright/tests/blog-multi-listing.spec.ts
new file mode 100644
index 00000000000..8ea82c55355
--- /dev/null
+++ b/tests/integration/playwright/tests/blog-multi-listing.spec.ts
@@ -0,0 +1,42 @@
+import { expect, Page, test } from "@playwright/test";
+import { getUrl } from "../src/utils";
+
+// Regression test for https://github.com/quarto-dev/quarto-cli/issues/14493:
+// when a post is in multiple listings, the post's category link must target
+// the nearest parent listing, not just the first entry in listings.json.
+
+const fixtureRoot = "blog/multi-listing-blog/_site";
+const alphaHrefPattern = /\/blog\/index\.html#category=alpha$/;
+
+const alphaLinkLocator = (page: Page) =>
+  page
+    .locator("header.quarto-title-block .quarto-category", { hasText: "alpha" })
+    .locator("a");
+
+test("Category link on a post resolves to the nearest parent listing", async ({ page }) => {
+  await page.goto(`./${fixtureRoot}/blog/post-one/`);
+
+  await expect(alphaLinkLocator(page)).toHaveAttribute("href", alphaHrefPattern);
+
+  await alphaLinkLocator(page).click();
+  await expect(page).toHaveURL(
+    getUrl(`${fixtureRoot}/blog/index.html#category=alpha`),
+  );
+  await expect(
+    page.locator(
+      `div.category[data-category="${btoa(encodeURIComponent("alpha"))}"]`,
+    ),
+  ).toHaveClass(/active/);
+  await expect(page.getByRole("link", { name: "Post one", exact: true })).toBeVisible();
+  await expect(page.getByRole("link", { name: "Post two", exact: true })).toBeVisible();
+});
+
+test("Category link on a post does not point at the homepage listing", async ({ page }) => {
+  // Reach the post from the homepage so document.referrer triggers the
+  // fallback branch that previously selected the wrong listing.
+  await page.goto(`./${fixtureRoot}/`);
+  await page.getByRole("link", { name: "Post one", exact: true }).click();
+  await expect(page).toHaveURL(getUrl(`${fixtureRoot}/blog/post-one/`));
+
+  await expect(alphaLinkLocator(page)).toHaveAttribute("href", alphaHrefPattern);
+});