diff --git a/.changeset/rotten-worms-walk.md b/.changeset/rotten-worms-walk.md
new file mode 100644
index 000000000000..a7a014056ea3
--- /dev/null
+++ b/.changeset/rotten-worms-walk.md
@@ -0,0 +1,6 @@
+---
+'@astrojs/image': patch
+'astro': patch
+---
+
+Avoid removing leading slash for `build.assetsPrefix` value in the build output
diff --git a/packages/astro/src/core/path.ts b/packages/astro/src/core/path.ts
index 8a0ac4a8676b..cbf959f69f57 100644
--- a/packages/astro/src/core/path.ts
+++ b/packages/astro/src/core/path.ts
@@ -52,7 +52,18 @@ function isString(path: unknown): path is string {
 }
 
 export function joinPaths(...paths: (string | undefined)[]) {
-	return paths.filter(isString).map(trimSlashes).join('/');
+	return paths
+		.filter(isString)
+		.map((path, i) => {
+			if (i === 0) {
+				return removeTrailingForwardSlash(path);
+			} else if (i === paths.length - 1) {
+				return removeLeadingForwardSlash(path);
+			} else {
+				return trimSlashes(path);
+			}
+		})
+		.join('/');
 }
 
 export function removeFileExtension(path: string) {
diff --git a/packages/astro/test/astro-assets-prefix.test.js b/packages/astro/test/astro-assets-prefix.test.js
index be80d460114d..58eb11e39b6a 100644
--- a/packages/astro/test/astro-assets-prefix.test.js
+++ b/packages/astro/test/astro-assets-prefix.test.js
@@ -63,6 +63,29 @@ describe('Assets Prefix - Static', () => {
 	});
 });
 
+describe('Assets Prefix - Static with path prefix', () => {
+	let fixture;
+
+	before(async () => {
+		fixture = await loadFixture({
+			root: './fixtures/astro-assets-prefix/',
+			build: {
+				assetsPrefix: '/starting-slash',
+			},
+		});
+		await fixture.build();
+	});
+
+	it('all stylesheets should start with assetPrefix', async () => {
+		const html = await fixture.readFile('/index.html');
+		const $ = cheerio.load(html);
+		const stylesheets = $('link[rel="stylesheet"]');
+		stylesheets.each((i, el) => {
+			expect(el.attribs.href).to.match(/^\/starting-slash\/.*/);
+		});
+	});
+});
+
 describe('Assets Prefix - Server', () => {
 	let app;
 
@@ -119,3 +142,32 @@ describe('Assets Prefix - Server', () => {
 		expect(imgAsset.attr('src')).to.match(assetsPrefixRegex);
 	});
 });
+
+describe('Assets Prefix - Server with path prefix', () => {
+	let app;
+
+	before(async () => {
+		const fixture = await loadFixture({
+			root: './fixtures/astro-assets-prefix/',
+			output: 'server',
+			adapter: testAdapter(),
+			build: {
+				assetsPrefix: '/starting-slash',
+			},
+		});
+		await fixture.build();
+		app = await fixture.loadTestAdapterApp();
+	});
+
+	it('all stylesheets should start with assetPrefix', async () => {
+		const request = new Request('http://example.com/custom-base/');
+		const response = await app.render(request);
+		expect(response.status).to.equal(200);
+		const html = await response.text();
+		const $ = cheerio.load(html);
+		const stylesheets = $('link[rel="stylesheet"]');
+		stylesheets.each((i, el) => {
+			expect(el.attribs.href).to.match(/^\/starting-slash\/.*/);
+		});
+	});
+});
diff --git a/packages/integrations/image/src/utils/paths.ts b/packages/integrations/image/src/utils/paths.ts
index 023fdc143d51..a6618ff1e9d5 100644
--- a/packages/integrations/image/src/utils/paths.ts
+++ b/packages/integrations/image/src/utils/paths.ts
@@ -75,5 +75,16 @@ function isString(path: unknown): path is string {
 }
 
 export function joinPaths(...paths: (string | undefined)[]) {
-	return paths.filter(isString).map(trimSlashes).join('/');
+	return paths
+		.filter(isString)
+		.map((path, i) => {
+			if (i === 0) {
+				return removeTrailingForwardSlash(path);
+			} else if (i === paths.length - 1) {
+				return removeLeadingForwardSlash(path);
+			} else {
+				return trimSlashes(path);
+			}
+		})
+		.join('/');
 }