From 1da7cbaaa0e96ca7f237dc536fada4f44ec7e79e Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Thu, 29 Jan 2026 16:36:54 +0100
Subject: [PATCH 01/13] feat(markdown/remark): Smartypants config

---
 packages/markdown/remark/src/index.ts |  5 +++--
 packages/markdown/remark/src/types.ts | 16 +++++++++++++++-
 2 files changed, 18 insertions(+), 3 deletions(-)

diff --git a/packages/markdown/remark/src/index.ts b/packages/markdown/remark/src/index.ts
index 634a883ebe98..4fcd8d304b72 100644
--- a/packages/markdown/remark/src/index.ts
+++ b/packages/markdown/remark/src/index.ts
@@ -90,8 +90,9 @@ export async function createMarkdownProcessor(
 		if (gfm) {
 			parser.use(remarkGfm);
 		}
-		if (smartypants) {
-			parser.use(remarkSmartypants);
+		if (smartypants !== false) {
+			const smartypantsConfig = typeof smartypants === 'object' ? smartypants : {};
+			parser.use(remarkSmartypants, smartypantsConfig);
 		}
 	}
 
diff --git a/packages/markdown/remark/src/types.ts b/packages/markdown/remark/src/types.ts
index 490d23fea859..fd9849538f19 100644
--- a/packages/markdown/remark/src/types.ts
+++ b/packages/markdown/remark/src/types.ts
@@ -35,6 +35,20 @@ export type RehypePlugins = (string | [string, any] | RehypePlugin | [RehypePlug
 
 export type RemarkRehype = RemarkRehypeOptions;
 
+export interface QuoteCharacterMap {
+	double: string;
+	single: string;
+}
+
+export interface SmartypantsOptions {
+	backticks?: boolean | 'all';
+	closingQuotes?: QuoteCharacterMap;
+	dashes?: boolean | 'oldschool' | 'inverted';
+	ellipses?: boolean | 'spaced' | 'unspaced';
+	openingQuotes?: QuoteCharacterMap;
+	quotes?: boolean;
+}
+
 export type ThemePresets = BuiltinTheme | 'css-variables';
 
 export type SyntaxHighlightConfigType = 'shiki' | 'prism';
@@ -58,7 +72,7 @@ export interface AstroMarkdownOptions {
 	rehypePlugins?: RehypePlugins;
 	remarkRehype?: RemarkRehype;
 	gfm?: boolean;
-	smartypants?: boolean;
+	smartypants?: boolean | SmartypantsOptions;
 }
 
 /**

From 3181557f5baf822ad5bd41f7d0d70502b59b1902 Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Thu, 29 Jan 2026 16:37:29 +0100
Subject: [PATCH 02/13] feat(astro): Smartypants config

---
 .../astro/src/core/config/schemas/base.ts     | 28 ++++++++++++++++++-
 1 file changed, 27 insertions(+), 1 deletion(-)

diff --git a/packages/astro/src/core/config/schemas/base.ts b/packages/astro/src/core/config/schemas/base.ts
index 0f494bdac904..73d727d08178 100644
--- a/packages/astro/src/core/config/schemas/base.ts
+++ b/packages/astro/src/core/config/schemas/base.ts
@@ -111,6 +111,26 @@ const highlighterTypesSchema = z
 	.union([z.literal('shiki'), z.literal('prism')])
 	.default(syntaxHighlightDefaults.type);
 
+const quoteCharacterMapSchema = z.object({
+	double: z.string(),
+	single: z.string(),
+});
+
+const smartypantsOptionsSchema = z.object({
+	backticks: z.union([z.boolean(), z.literal('all')]).default(true),
+	closingQuotes: quoteCharacterMapSchema.default({
+		double: '”',
+		single: '’',
+	}),
+	dashes: z.union([z.boolean(), z.literal('inverted'), z.literal('oldschool')]).default(true),
+	ellipses: z.union([z.boolean(), z.literal('spaced'), z.literal('unspaced')]).default(true),
+	openingQuotes: quoteCharacterMapSchema.default({
+		double: '“',
+		single: '‘',
+	}),
+	quotes: z.boolean().default(true),
+});
+
 export const AstroConfigSchema = z.object({
 	root: z
 		.string()
@@ -377,7 +397,13 @@ export const AstroConfigSchema = z.object({
 				.custom<RemarkRehype>((data) => data instanceof Object && !Array.isArray(data))
 				.default(ASTRO_CONFIG_DEFAULTS.markdown.remarkRehype),
 			gfm: z.boolean().default(ASTRO_CONFIG_DEFAULTS.markdown.gfm),
-			smartypants: z.boolean().default(ASTRO_CONFIG_DEFAULTS.markdown.smartypants),
+			smartypants: z
+				.union([z.boolean(), smartypantsOptionsSchema])
+				.default(ASTRO_CONFIG_DEFAULTS.markdown.smartypants)
+				.transform((val) => {
+					if (val === true) return smartypantsOptionsSchema.parse({});
+					return val;
+				}),
 		})
 		.prefault({}),
 	vite: z

From 9dd6f22f403296096a8db17a352d5e26b7d43d2c Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Thu, 29 Jan 2026 16:37:54 +0100
Subject: [PATCH 03/13] test: add e2e Smartypants config tests

---
 .../astro/test/astro-markdown-plugins.test.js | 79 ++++++++++++++++++-
 .../src/pages/with-backticks.md               |  3 +
 .../src/pages/with-smartypants.md             |  2 +-
 3 files changed, 80 insertions(+), 4 deletions(-)
 create mode 100644 packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-backticks.md

diff --git a/packages/astro/test/astro-markdown-plugins.test.js b/packages/astro/test/astro-markdown-plugins.test.js
index 78db0e6dcbf6..d5e0f66d2ba9 100644
--- a/packages/astro/test/astro-markdown-plugins.test.js
+++ b/packages/astro/test/astro-markdown-plugins.test.js
@@ -60,7 +60,7 @@ describe('Astro Markdown plugins', () => {
 
 			const smartypantsHtml = await fixture.readFile('/with-smartypants/index.html');
 			const $2 = cheerio.load(smartypantsHtml);
-			assert.equal($2('p').html(), '“Smartypants” is — awesome');
+			assert.equal($2('p').html(), '“Smartypants” is — awesome …');
 
 			testRemark(gfmHtml);
 			testRehype(gfmHtml, '#github-flavored-markdown-test');
@@ -82,7 +82,7 @@ describe('Astro Markdown plugins', () => {
 			const $ = cheerio.load(html);
 
 			// test 1: smartypants applied correctly
-			assert.equal($('p').html(), '“Smartypants” is — awesome');
+			assert.equal($('p').html(), '“Smartypants” is — awesome …');
 
 			testRemark(html);
 			testRehype(html, '#smartypants-test');
@@ -115,7 +115,7 @@ describe('Astro Markdown plugins', () => {
 		const html = await fixture.readFile('/with-smartypants/index.html');
 		const $ = cheerio.load(html);
 
-		assert.equal($('p').html(), '"Smartypants" is -- awesome');
+		assert.equal($('p').html(), '"Smartypants" is -- awesome ...');
 
 		testRemark(html);
 		testRehype(html, '#smartypants-test');
@@ -146,6 +146,79 @@ describe('Astro Markdown plugins', () => {
 			);
 		});
 	});
+
+	describe('Advanced Smartypants configurations', () => {
+		it('Handles custom dashes (oldschool)', async () => {
+			const fixture = await loadFixture({
+				root: './fixtures/astro-markdown-plugins/',
+				markdown: {
+					...defaultMarkdownConfig,
+					smartypants: { dashes: 'oldschool' },
+				},
+			});
+			await fixture.build();
+
+			const html = await fixture.readFile('/with-smartypants/index.html');
+			const $ = cheerio.load(html);
+
+			// In 'oldschool', -- becomes en-dash (–) instead of em-dash (—)
+			assert.equal($('p').html(), '“Smartypants” is – awesome …');
+		});
+
+		it('Handles disabled ellipses', async () => {
+			const fixture = await loadFixture({
+				root: './fixtures/astro-markdown-plugins/',
+				markdown: {
+					...defaultMarkdownConfig,
+					smartypants: { ellipses: false },
+				},
+			});
+			await fixture.build();
+
+			const html = await fixture.readFile('/with-smartypants/index.html');
+			const $ = cheerio.load(html);
+
+			// Dashes should still be smart (em-dash), but dots should remain dots
+			assert.equal($('p').html(), '“Smartypants” is — awesome ...');
+		});
+
+		it('Handles custom opening and closing quotes', async () => {
+			const fixture = await loadFixture({
+				root: './fixtures/astro-markdown-plugins/',
+				markdown: {
+					...defaultMarkdownConfig,
+					smartypants: {
+						openingQuotes: { double: '«', single: '‹' },
+						closingQuotes: { double: '»', single: '›' },
+					},
+				},
+			});
+			await fixture.build();
+
+			const html = await fixture.readFile('/with-smartypants/index.html');
+			const $ = cheerio.load(html);
+
+			// Verify the custom guillemets are used
+			assert.equal($('p').html(), '«Smartypants» is — awesome …');
+		});
+
+		it('Handles backticks: "all"', async () => {
+			const fixture = await loadFixture({
+				root: './fixtures/astro-markdown-plugins/',
+				markdown: {
+					...defaultMarkdownConfig,
+					smartypants: { backticks: 'all', quotes: false },
+				},
+			});
+			await fixture.build();
+
+			const html = await fixture.readFile('/with-backticks/index.html');
+			const $ = cheerio.load(html);
+
+			// With backticks: 'all', single and double backticks are transformed
+			assert.ok($('p').html().includes('“Smarty”'));
+		});
+	});
 });
 
 function testRehype(html, headingId) {
diff --git a/packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-backticks.md b/packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-backticks.md
new file mode 100644
index 000000000000..514e476ca7bd
--- /dev/null
+++ b/packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-backticks.md
@@ -0,0 +1,3 @@
+# Smartypants Backticks test
+
+``Smarty''
diff --git a/packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-smartypants.md b/packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-smartypants.md
index 5d7a85ab1ac8..0538abc98008 100644
--- a/packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-smartypants.md
+++ b/packages/astro/test/fixtures/astro-markdown-plugins/src/pages/with-smartypants.md
@@ -1,3 +1,3 @@
 # Smartypants test
 
-"Smartypants" is -- awesome
+"Smartypants" is -- awesome ...

From e12dc7e700b19762efd24271f6db81b1ae064a47 Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Thu, 29 Jan 2026 17:01:54 +0100
Subject: [PATCH 04/13] docs: add changesets

---
 .changeset/legal-rings-rhyme.md | 21 +++++++++++++++++++++
 .changeset/red-heads-stare.md   | 27 +++++++++++++++++++++++++++
 2 files changed, 48 insertions(+)
 create mode 100644 .changeset/legal-rings-rhyme.md
 create mode 100644 .changeset/red-heads-stare.md

diff --git a/.changeset/legal-rings-rhyme.md b/.changeset/legal-rings-rhyme.md
new file mode 100644
index 000000000000..e213f2c335b3
--- /dev/null
+++ b/.changeset/legal-rings-rhyme.md
@@ -0,0 +1,21 @@
+---
+'@astrojs/markdown-remark': minor
+---
+
+Updates `createMarkdownProcessor` to support advanced SmartyPants options.
+
+The `smartypants` property in `AstroMarkdownOptions` now accepts a `SmartypantsOptions` object, allowing fine-grained control over typography transformations (backticks, dashes, ellipses, and quotes).
+
+```ts
+import { createMarkdownProcessor } from '@astrojs/markdown-remark';
+
+const processor = await createMarkdownProcessor({
+  smartypants: {
+    backticks: 'all',
+    dashes: 'oldschool',
+    ellipses: 'unspaced',
+    openingQuotes: { double: '«', single: '‹' },
+    closingQuotes: { double: '»', single: '›' },
+    quotes: false,
+  }
+});
diff --git a/.changeset/red-heads-stare.md b/.changeset/red-heads-stare.md
new file mode 100644
index 000000000000..78e101edc0c8
--- /dev/null
+++ b/.changeset/red-heads-stare.md
@@ -0,0 +1,27 @@
+---
+'astro': minor
+---
+
+Adds support for advanced configuration of SmartyPants in Markdown.
+
+You can now pass an options object to `markdown.smartypants` in your Astro configuration to fine-tune how punctuation, dashes, and quotes are transformed.
+
+This is helpful for projects that require specific typographic standards, such as "oldschool" dash handling or localized quotation marks.
+
+```js
+// astro.config.mjs
+export default defineConfig({
+  markdown: {
+    smartypants: {
+      backticks: 'all',
+      dashes: 'oldschool',
+      ellipses: 'unspaced',
+      openingQuotes: { double: '«', single: '‹' },
+      closingQuotes: { double: '»', single: '›' },
+      quotes: false,
+    },
+  },
+});
+```
+
+See [the `markdown.smartypants` reference documentation](https://docs.astro.build/en/reference/configuration-reference/#markdownsmartypants) for more information.

From 897dd46ccc35aee0bb65b2a16b7dea1f84a77db7 Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Thu, 29 Jan 2026 17:02:28 +0100
Subject: [PATCH 05/13] docs: update public Astro config types docs

this file is used to autogenerate the configuration reference documentation
---
 packages/astro/src/types/public/config.ts | 101 +++++++++++++++++++---
 1 file changed, 91 insertions(+), 10 deletions(-)

diff --git a/packages/astro/src/types/public/config.ts b/packages/astro/src/types/public/config.ts
index 3c522f74f08c..46afacc81942 100644
--- a/packages/astro/src/types/public/config.ts
+++ b/packages/astro/src/types/public/config.ts
@@ -1,10 +1,12 @@
 import type { OutgoingHttpHeaders } from 'node:http';
 import type { RemotePattern } from '@astrojs/internal-helpers/remote';
 import type {
+	QuoteCharacterMap,
 	RehypePlugins,
 	RemarkPlugins,
 	RemarkRehype,
 	ShikiConfig,
+	SmartypantsOptions,
 	SyntaxHighlightConfigType,
 } from '@astrojs/markdown-remark';
 import type { Config as SvgoConfig } from 'svgo';
@@ -1947,24 +1949,103 @@ export interface AstroUserConfig<
 		 * ```
 		 */
 		gfm?: boolean;
+
 		/**
 		 * @docs
 		 * @name markdown.smartypants
-		 * @type {boolean}
+		 * @type {boolean | SmartypantsOptions}
 		 * @default `true`
 		 * @version 2.0.0
 		 * @description
-		 * Astro uses the [SmartyPants formatter](https://daringfireball.net/projects/smartypants/) by default. To disable this, set the `smartypants` flag to `false`:
+		 * Whether to use the [SmartyPants formatter](https://daringfireball.net/projects/smartypants/) to transform straight quotes into smart quotes, dashes into en/em dashes, and triple dots into ellipses.
 		 *
-		 * ```js
-		 * {
-		 *   markdown: {
-		 *     smartypants: false,
-		 *   }
-		 * }
-		 * ```
+		 * To disable this, set the `smartypants` flag to `false`.
+		 *
+		 * For more control over typography, you can instead specify a configuration object with the properties listed below.
 		 */
-		smartypants?: boolean;
+		smartypants?:
+			| boolean
+			| {
+					/**
+					 * @docs
+					 * @name markdown.smartypants.backticks
+					 * @kind h4
+					 * @type {boolean | 'all'}
+					 * @default `true`
+					 * @version 5.18.0
+					 * @description
+					 * Whether to transform backticks into smart quotes.
+					 * When set to `'all'`, double backticks are converted to double quotes and single backticks are converted to single quotes.
+					 */
+					backticks?: boolean | 'all';
+
+					/**
+					 * @docs
+					 * @name markdown.smartypants.quotes
+					 * @kind h4
+					 * @type {boolean}
+					 * @default `true`
+					 * @version 5.18.0
+					 * @description
+					 * Whether to transform straight quotes into curly "smart" quotes.
+					 * * Note: If `backticks` is set to `'all'`, this should typically be set to `false`.
+					 */
+					quotes?: boolean;
+
+					/**
+					 * @docs
+					 * @name markdown.smartypants.dashes
+					 * @kind h4
+					 * @type {boolean | 'oldschool' | 'inverted'}
+					 * @default `true`
+					 * @version 5.18.0
+					 * @description
+					 * How to transform dashes.
+					 * - `true`: turns two dashes into an em dash.
+					 * - `'oldschool'`: turns three dashes into an em dash and two into an en dash.
+					 * - `'inverted'`: turns three dashes into an en dash and two into an em dash.
+					 */
+					dashes?: boolean | 'oldschool' | 'inverted';
+
+					/**
+					 * @docs
+					 * @name markdown.smartypants.ellipses
+					 * @kind h4
+					 * @type {boolean | 'spaced' | 'unspaced'}
+					 * @default `true`
+					 * @version 5.18.0
+					 * @description
+					 * Whether to transform triple dots into ellipses.
+					 * - `'spaced'`: only transforms triple dots with spaces (e.g. `. . .`).
+					 * - `'unspaced'`: only transforms triple dots without spaces (e.g. `...`).
+					 */
+					ellipses?: boolean | 'spaced' | 'unspaced';
+
+					/**
+					 * @docs
+					 * @name markdown.smartypants.openingQuotes
+					 * @kind h4
+					 * @type {QuoteCharacterMap}
+					 * @default `{ double: '“', single: '‘' }`
+					 * @version 5.18.0
+					 * @description
+					 * The specific characters to use for opening double and single quotes.
+					 */
+					openingQuotes?: QuoteCharacterMap;
+
+					/**
+					 * @docs
+					 * @name markdown.smartypants.closingQuotes
+					 * @kind h4
+					 * @type {QuoteCharacterMap}
+					 * @default `{ double: '”', single: '’' }`
+					 * @version 5.18.0
+					 * @description
+					 * The specific characters to use for closing double and single quotes.
+					 */
+					closingQuotes?: QuoteCharacterMap;
+			  };
+
 		/**
 		 * @docs
 		 * @name markdown.remarkRehype

From 7ca04cfef23212a2aa6bdeb2c0948d539529d463 Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Thu, 29 Jan 2026 17:28:51 +0100
Subject: [PATCH 06/13] fix: unused import

---
 packages/astro/src/types/public/config.ts | 1 -
 1 file changed, 1 deletion(-)

diff --git a/packages/astro/src/types/public/config.ts b/packages/astro/src/types/public/config.ts
index 46afacc81942..320674680360 100644
--- a/packages/astro/src/types/public/config.ts
+++ b/packages/astro/src/types/public/config.ts
@@ -6,7 +6,6 @@ import type {
 	RemarkPlugins,
 	RemarkRehype,
 	ShikiConfig,
-	SmartypantsOptions,
 	SyntaxHighlightConfigType,
 } from '@astrojs/markdown-remark';
 import type { Config as SvgoConfig } from 'svgo';

From 4f302de9f4c1c08976a7849c522b2959c526c92f Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Fri, 30 Jan 2026 08:23:31 +0100
Subject: [PATCH 07/13] feat: change docs version

---
 packages/astro/src/types/public/config.ts | 12 ++++++------
 1 file changed, 6 insertions(+), 6 deletions(-)

diff --git a/packages/astro/src/types/public/config.ts b/packages/astro/src/types/public/config.ts
index 320674680360..dc7eccd0132a 100644
--- a/packages/astro/src/types/public/config.ts
+++ b/packages/astro/src/types/public/config.ts
@@ -1971,7 +1971,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean | 'all'}
 					 * @default `true`
-					 * @version 5.18.0
+					 * @version 6.0.0
 					 * @description
 					 * Whether to transform backticks into smart quotes.
 					 * When set to `'all'`, double backticks are converted to double quotes and single backticks are converted to single quotes.
@@ -1984,7 +1984,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean}
 					 * @default `true`
-					 * @version 5.18.0
+					 * @version 6.0.0
 					 * @description
 					 * Whether to transform straight quotes into curly "smart" quotes.
 					 * * Note: If `backticks` is set to `'all'`, this should typically be set to `false`.
@@ -1997,7 +1997,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean | 'oldschool' | 'inverted'}
 					 * @default `true`
-					 * @version 5.18.0
+					 * @version 6.0.0
 					 * @description
 					 * How to transform dashes.
 					 * - `true`: turns two dashes into an em dash.
@@ -2012,7 +2012,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean | 'spaced' | 'unspaced'}
 					 * @default `true`
-					 * @version 5.18.0
+					 * @version 6.0.0
 					 * @description
 					 * Whether to transform triple dots into ellipses.
 					 * - `'spaced'`: only transforms triple dots with spaces (e.g. `. . .`).
@@ -2026,7 +2026,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {QuoteCharacterMap}
 					 * @default `{ double: '“', single: '‘' }`
-					 * @version 5.18.0
+					 * @version 6.0.0
 					 * @description
 					 * The specific characters to use for opening double and single quotes.
 					 */
@@ -2038,7 +2038,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {QuoteCharacterMap}
 					 * @default `{ double: '”', single: '’' }`
-					 * @version 5.18.0
+					 * @version 6.0.0
 					 * @description
 					 * The specific characters to use for closing double and single quotes.
 					 */

From 92c89389c8d47ca526f29fdd9c44532cf8e6d60e Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Sat, 14 Mar 2026 08:27:21 +0100
Subject: [PATCH 08/13] feat: set since version in config to 6.1.0

---
 packages/astro/src/types/public/config.ts | 12 ++++++------
 1 file changed, 6 insertions(+), 6 deletions(-)

diff --git a/packages/astro/src/types/public/config.ts b/packages/astro/src/types/public/config.ts
index 069b3b99fae1..505cbeb80fb8 100644
--- a/packages/astro/src/types/public/config.ts
+++ b/packages/astro/src/types/public/config.ts
@@ -2064,7 +2064,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean | 'all'}
 					 * @default `true`
-					 * @version 6.0.0
+					 * @version 6.1.0
 					 * @description
 					 * Whether to transform backticks into smart quotes.
 					 * When set to `'all'`, double backticks are converted to double quotes and single backticks are converted to single quotes.
@@ -2077,7 +2077,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean}
 					 * @default `true`
-					 * @version 6.0.0
+					 * @version 6.1.0
 					 * @description
 					 * Whether to transform straight quotes into curly "smart" quotes.
 					 * * Note: If `backticks` is set to `'all'`, this should typically be set to `false`.
@@ -2090,7 +2090,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean | 'oldschool' | 'inverted'}
 					 * @default `true`
-					 * @version 6.0.0
+					 * @version 6.1.0
 					 * @description
 					 * How to transform dashes.
 					 * - `true`: turns two dashes into an em dash.
@@ -2105,7 +2105,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {boolean | 'spaced' | 'unspaced'}
 					 * @default `true`
-					 * @version 6.0.0
+					 * @version 6.1.0
 					 * @description
 					 * Whether to transform triple dots into ellipses.
 					 * - `'spaced'`: only transforms triple dots with spaces (e.g. `. . .`).
@@ -2119,7 +2119,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {QuoteCharacterMap}
 					 * @default `{ double: '“', single: '‘' }`
-					 * @version 6.0.0
+					 * @version 6.1.0
 					 * @description
 					 * The specific characters to use for opening double and single quotes.
 					 */
@@ -2131,7 +2131,7 @@ export interface AstroUserConfig<
 					 * @kind h4
 					 * @type {QuoteCharacterMap}
 					 * @default `{ double: '”', single: '’' }`
-					 * @version 6.0.0
+					 * @version 6.1.0
 					 * @description
 					 * The specific characters to use for closing double and single quotes.
 					 */

From ae92fb28144fdc0f2f002ab71b0d3e88764c9801 Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Sat, 14 Mar 2026 09:35:07 +0100
Subject: [PATCH 09/13] fix: adapt default type definition

---
 packages/astro/src/core/config/schemas/base.ts | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/packages/astro/src/core/config/schemas/base.ts b/packages/astro/src/core/config/schemas/base.ts
index 325c9bfeeecf..5efd593d38ab 100644
--- a/packages/astro/src/core/config/schemas/base.ts
+++ b/packages/astro/src/core/config/schemas/base.ts
@@ -407,11 +407,11 @@ export const AstroConfigSchema = z.object({
 			gfm: z.boolean().default(ASTRO_CONFIG_DEFAULTS.markdown.gfm),
 			smartypants: z
 				.union([z.boolean(), smartypantsOptionsSchema])
-				.default(ASTRO_CONFIG_DEFAULTS.markdown.smartypants)
 				.transform((val) => {
 					if (val === true) return smartypantsOptionsSchema.parse({});
 					return val;
-				}),
+				})
+				.default(smartypantsOptionsSchema.parse({})),
 		})
 		.prefault({}),
 	vite: z

From 09778a80937b17ff9e771c323ce3c26494dfeb0e Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Wed, 25 Mar 2026 16:00:48 +0100
Subject: [PATCH 10/13] refactor: use retext-smartypants options

---
 .changeset/legal-rings-rhyme.md               |  5 +-
 .changeset/red-heads-stare.md                 |  2 +-
 .../astro/src/core/config/schemas/base.ts     |  8 +-
 packages/astro/src/types/public/config.ts     | 87 +------------------
 packages/markdown/remark/package.json         |  1 +
 packages/markdown/remark/src/types.ts         | 15 +---
 pnpm-lock.yaml                                |  3 +
 7 files changed, 20 insertions(+), 101 deletions(-)

diff --git a/.changeset/legal-rings-rhyme.md b/.changeset/legal-rings-rhyme.md
index e213f2c335b3..f989a59e08cb 100644
--- a/.changeset/legal-rings-rhyme.md
+++ b/.changeset/legal-rings-rhyme.md
@@ -4,7 +4,7 @@
 
 Updates `createMarkdownProcessor` to support advanced SmartyPants options.
 
-The `smartypants` property in `AstroMarkdownOptions` now accepts a `SmartypantsOptions` object, allowing fine-grained control over typography transformations (backticks, dashes, ellipses, and quotes).
+The `smartypants` property in `AstroMarkdownOptions` now accepts `Smartypants` options, allowing fine-grained control over typography transformations (backticks, dashes, ellipses, and quotes).
 
 ```ts
 import { createMarkdownProcessor } from '@astrojs/markdown-remark';
@@ -19,3 +19,6 @@ const processor = await createMarkdownProcessor({
     quotes: false,
   }
 });
+```
+
+For the up-to-date supported properties, check out [the `retext-smartypants` options](https://github.com/retextjs/retext-smartypants?tab=readme-ov-file#fields).
diff --git a/.changeset/red-heads-stare.md b/.changeset/red-heads-stare.md
index 78e101edc0c8..342f19737188 100644
--- a/.changeset/red-heads-stare.md
+++ b/.changeset/red-heads-stare.md
@@ -24,4 +24,4 @@ export default defineConfig({
 });
 ```
 
-See [the `markdown.smartypants` reference documentation](https://docs.astro.build/en/reference/configuration-reference/#markdownsmartypants) for more information.
+See [the `retext-smartypants` options](https://github.com/retextjs/retext-smartypants?tab=readme-ov-file#fields) for more information.
diff --git a/packages/astro/src/core/config/schemas/base.ts b/packages/astro/src/core/config/schemas/base.ts
index 5efd593d38ab..49be664cb75f 100644
--- a/packages/astro/src/core/config/schemas/base.ts
+++ b/packages/astro/src/core/config/schemas/base.ts
@@ -4,6 +4,7 @@ import type {
 	RemarkPlugin as _RemarkPlugin,
 	RemarkRehype as _RemarkRehype,
 	ShikiConfig,
+	Smartypants as _Smartypants,
 } from '@astrojs/markdown-remark';
 import { markdownConfigDefaults, syntaxHighlightDefaults } from '@astrojs/markdown-remark';
 import { type BuiltinTheme, bundledThemes } from 'shiki';
@@ -49,6 +50,7 @@ type RehypePlugin = ComplexifyWithUnion<_RehypePlugin>;
 type RemarkPlugin = ComplexifyWithUnion<_RemarkPlugin>;
 /** @lintignore */
 export type RemarkRehype = ComplexifyWithOmit<_RemarkRehype>;
+export type Smartypants = ComplexifyWithOmit<_Smartypants>;
 
 export const ASTRO_CONFIG_DEFAULTS = {
 	root: '.',
@@ -123,7 +125,7 @@ const quoteCharacterMapSchema = z.object({
 	single: z.string(),
 });
 
-const smartypantsOptionsSchema = z.object({
+const smartypantsOptionsSchema: z.ZodType<Smartypants> = z.object({
 	backticks: z.union([z.boolean(), z.literal('all')]).default(true),
 	closingQuotes: quoteCharacterMapSchema.default({
 		double: '”',
@@ -407,11 +409,11 @@ export const AstroConfigSchema = z.object({
 			gfm: z.boolean().default(ASTRO_CONFIG_DEFAULTS.markdown.gfm),
 			smartypants: z
 				.union([z.boolean(), smartypantsOptionsSchema])
-				.transform((val) => {
+				.transform((val): false | Smartypants => {
 					if (val === true) return smartypantsOptionsSchema.parse({});
 					return val;
 				})
-				.default(smartypantsOptionsSchema.parse({})),
+				.prefault(ASTRO_CONFIG_DEFAULTS.markdown.smartypants),
 		})
 		.prefault({}),
 	vite: z
diff --git a/packages/astro/src/types/public/config.ts b/packages/astro/src/types/public/config.ts
index 505cbeb80fb8..541199a0f055 100644
--- a/packages/astro/src/types/public/config.ts
+++ b/packages/astro/src/types/public/config.ts
@@ -1,11 +1,11 @@
 import type { OutgoingHttpHeaders } from 'node:http';
 import type { RemotePattern } from '@astrojs/internal-helpers/remote';
 import type {
-	QuoteCharacterMap,
 	RehypePlugins,
 	RemarkPlugins,
 	RemarkRehype,
 	ShikiConfig,
+	Smartypants,
 	SyntaxHighlightConfigType,
 } from '@astrojs/markdown-remark';
 import type { Config as SvgoConfig } from 'svgo';
@@ -2045,7 +2045,7 @@ export interface AstroUserConfig<
 		/**
 		 * @docs
 		 * @name markdown.smartypants
-		 * @type {boolean | SmartypantsOptions}
+		 * @type {boolean | Smartypants}
 		 * @default `true`
 		 * @version 2.0.0
 		 * @description
@@ -2053,90 +2053,11 @@ export interface AstroUserConfig<
 		 *
 		 * To disable this, set the `smartypants` flag to `false`.
 		 *
-		 * For more control over typography, you can instead specify a configuration object with the properties listed below.
+		 * For more control over typography, you can instead specify a configuration object with the properties [supported by `retext-smartypants`](https://github.com/retextjs/retext-smartypants?tab=readme-ov-file#fields).
 		 */
 		smartypants?:
 			| boolean
-			| {
-					/**
-					 * @docs
-					 * @name markdown.smartypants.backticks
-					 * @kind h4
-					 * @type {boolean | 'all'}
-					 * @default `true`
-					 * @version 6.1.0
-					 * @description
-					 * Whether to transform backticks into smart quotes.
-					 * When set to `'all'`, double backticks are converted to double quotes and single backticks are converted to single quotes.
-					 */
-					backticks?: boolean | 'all';
-
-					/**
-					 * @docs
-					 * @name markdown.smartypants.quotes
-					 * @kind h4
-					 * @type {boolean}
-					 * @default `true`
-					 * @version 6.1.0
-					 * @description
-					 * Whether to transform straight quotes into curly "smart" quotes.
-					 * * Note: If `backticks` is set to `'all'`, this should typically be set to `false`.
-					 */
-					quotes?: boolean;
-
-					/**
-					 * @docs
-					 * @name markdown.smartypants.dashes
-					 * @kind h4
-					 * @type {boolean | 'oldschool' | 'inverted'}
-					 * @default `true`
-					 * @version 6.1.0
-					 * @description
-					 * How to transform dashes.
-					 * - `true`: turns two dashes into an em dash.
-					 * - `'oldschool'`: turns three dashes into an em dash and two into an en dash.
-					 * - `'inverted'`: turns three dashes into an en dash and two into an em dash.
-					 */
-					dashes?: boolean | 'oldschool' | 'inverted';
-
-					/**
-					 * @docs
-					 * @name markdown.smartypants.ellipses
-					 * @kind h4
-					 * @type {boolean | 'spaced' | 'unspaced'}
-					 * @default `true`
-					 * @version 6.1.0
-					 * @description
-					 * Whether to transform triple dots into ellipses.
-					 * - `'spaced'`: only transforms triple dots with spaces (e.g. `. . .`).
-					 * - `'unspaced'`: only transforms triple dots without spaces (e.g. `...`).
-					 */
-					ellipses?: boolean | 'spaced' | 'unspaced';
-
-					/**
-					 * @docs
-					 * @name markdown.smartypants.openingQuotes
-					 * @kind h4
-					 * @type {QuoteCharacterMap}
-					 * @default `{ double: '“', single: '‘' }`
-					 * @version 6.1.0
-					 * @description
-					 * The specific characters to use for opening double and single quotes.
-					 */
-					openingQuotes?: QuoteCharacterMap;
-
-					/**
-					 * @docs
-					 * @name markdown.smartypants.closingQuotes
-					 * @kind h4
-					 * @type {QuoteCharacterMap}
-					 * @default `{ double: '”', single: '’' }`
-					 * @version 6.1.0
-					 * @description
-					 * The specific characters to use for closing double and single quotes.
-					 */
-					closingQuotes?: QuoteCharacterMap;
-			  };
+			| Smartypants;
 
 		/**
 		 * @docs
diff --git a/packages/markdown/remark/package.json b/packages/markdown/remark/package.json
index 0ba0e4f23de8..d51a0693f7f3 100644
--- a/packages/markdown/remark/package.json
+++ b/packages/markdown/remark/package.json
@@ -50,6 +50,7 @@
     "remark-parse": "^11.0.0",
     "remark-rehype": "^11.1.2",
     "remark-smartypants": "^3.0.2",
+    "retext-smartypants": "^6.2.0",
     "shiki": "^4.0.0",
     "smol-toml": "^1.6.0",
     "unified": "^11.0.5",
diff --git a/packages/markdown/remark/src/types.ts b/packages/markdown/remark/src/types.ts
index fd9849538f19..fb4d9d7a95c9 100644
--- a/packages/markdown/remark/src/types.ts
+++ b/packages/markdown/remark/src/types.ts
@@ -2,6 +2,7 @@ import type { RemotePattern } from '@astrojs/internal-helpers/remote';
 import type * as hast from 'hast';
 import type * as mdast from 'mdast';
 import type { Options as RemarkRehypeOptions } from 'remark-rehype';
+import type { Options as SmartypantsOptions } from "retext-smartypants";
 import type { BuiltinTheme } from 'shiki';
 import type * as unified from 'unified';
 import type { CreateShikiHighlighterOptions, ShikiHighlighterHighlightOptions } from './shiki.js';
@@ -35,19 +36,7 @@ export type RehypePlugins = (string | [string, any] | RehypePlugin | [RehypePlug
 
 export type RemarkRehype = RemarkRehypeOptions;
 
-export interface QuoteCharacterMap {
-	double: string;
-	single: string;
-}
-
-export interface SmartypantsOptions {
-	backticks?: boolean | 'all';
-	closingQuotes?: QuoteCharacterMap;
-	dashes?: boolean | 'oldschool' | 'inverted';
-	ellipses?: boolean | 'spaced' | 'unspaced';
-	openingQuotes?: QuoteCharacterMap;
-	quotes?: boolean;
-}
+export type Smartypants = SmartypantsOptions;
 
 export type ThemePresets = BuiltinTheme | 'css-variables';
 
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 445726cad266..66b7d31a3985 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -6992,6 +6992,9 @@ importers:
       remark-smartypants:
         specifier: ^3.0.2
         version: 3.0.2
+      retext-smartypants:
+        specifier: ^6.2.0
+        version: 6.2.0
       shiki:
         specifier: ^4.0.0
         version: 4.0.2

From 83ff9164e69d3750472f39d79bc5e781718466bf Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Wed, 25 Mar 2026 16:04:22 +0100
Subject: [PATCH 11/13] fix: remove export of Smartypants type from astro core

---
 packages/astro/src/core/config/schemas/base.ts | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/packages/astro/src/core/config/schemas/base.ts b/packages/astro/src/core/config/schemas/base.ts
index 49be664cb75f..bc2e4b9bc312 100644
--- a/packages/astro/src/core/config/schemas/base.ts
+++ b/packages/astro/src/core/config/schemas/base.ts
@@ -50,7 +50,7 @@ type RehypePlugin = ComplexifyWithUnion<_RehypePlugin>;
 type RemarkPlugin = ComplexifyWithUnion<_RemarkPlugin>;
 /** @lintignore */
 export type RemarkRehype = ComplexifyWithOmit<_RemarkRehype>;
-export type Smartypants = ComplexifyWithOmit<_Smartypants>;
+type Smartypants = ComplexifyWithOmit<_Smartypants>;
 
 export const ASTRO_CONFIG_DEFAULTS = {
 	root: '.',

From 559bc7fd566b616fc574fe7837688ad4952d0d13 Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Wed, 25 Mar 2026 16:06:58 +0100
Subject: [PATCH 12/13] fix: reexport Smartypants type but lintignore it

---
 packages/astro/src/core/config/schemas/base.ts | 3 ++-
 1 file changed, 2 insertions(+), 1 deletion(-)

diff --git a/packages/astro/src/core/config/schemas/base.ts b/packages/astro/src/core/config/schemas/base.ts
index bc2e4b9bc312..f9cc154f3f1e 100644
--- a/packages/astro/src/core/config/schemas/base.ts
+++ b/packages/astro/src/core/config/schemas/base.ts
@@ -50,7 +50,8 @@ type RehypePlugin = ComplexifyWithUnion<_RehypePlugin>;
 type RemarkPlugin = ComplexifyWithUnion<_RemarkPlugin>;
 /** @lintignore */
 export type RemarkRehype = ComplexifyWithOmit<_RemarkRehype>;
-type Smartypants = ComplexifyWithOmit<_Smartypants>;
+/** @lintignore */
+export type Smartypants = ComplexifyWithOmit<_Smartypants>;
 
 export const ASTRO_CONFIG_DEFAULTS = {
 	root: '.',

From 179938e2769adaa6e0c2abae59b10b384307f26c Mon Sep 17 00:00:00 2001
From: Felix Schneider <99918022+trueberryless@users.noreply.github.com>
Date: Wed, 25 Mar 2026 16:47:30 +0100
Subject: [PATCH 13/13] Update packages/astro/src/types/public/config.ts

Co-authored-by: Armand Philippot <git@armand.philippot.eu>
---
 packages/astro/src/types/public/config.ts | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/packages/astro/src/types/public/config.ts b/packages/astro/src/types/public/config.ts
index 541199a0f055..d1cfb0ff44fe 100644
--- a/packages/astro/src/types/public/config.ts
+++ b/packages/astro/src/types/public/config.ts
@@ -2053,7 +2053,7 @@ export interface AstroUserConfig<
 		 *
 		 * To disable this, set the `smartypants` flag to `false`.
 		 *
-		 * For more control over typography, you can instead specify a configuration object with the properties [supported by `retext-smartypants`](https://github.com/retextjs/retext-smartypants?tab=readme-ov-file#fields).
+		 * For more control over typography, you can instead specify a configuration object with the [properties supported by `retext-smartypants`](https://github.com/retextjs/retext-smartypants?tab=readme-ov-file#fields).
 		 */
 		smartypants?:
 			| boolean