diff --git a/.changeset/happy-deers-wait.md b/.changeset/happy-deers-wait.md
new file mode 100644
index 000000000..b71454942
--- /dev/null
+++ b/.changeset/happy-deers-wait.md
@@ -0,0 +1,8 @@
+---
+'@compiled/babel-plugin': patch
+---
+
+Fix handling of `content` property.
+
+- The value of the `content` property will no longer automatically have quotes erroneously added around it, if the value is one of `open-quote`, `counter(...)`, `url(...)`, `inherit`, `none`, and so on.
+- The full regex used to check is as follows: `/^([A-Za-z\-]+\([^]*|[^]*-quote|inherit|initial|none|normal|revert|unset)(\s|$)/`
diff --git a/packages/babel-plugin/src/styled/__tests__/content-property.test.ts b/packages/babel-plugin/src/styled/__tests__/content-property.test.ts
new file mode 100644
index 000000000..2fb4ddf4d
--- /dev/null
+++ b/packages/babel-plugin/src/styled/__tests__/content-property.test.ts
@@ -0,0 +1,177 @@
+import type { TransformOptions } from '../../test-utils';
+import { transform as transformCode } from '../../test-utils';
+
+describe('handling of values for CSS `content` property', () => {
+  beforeAll(() => {
+    process.env.AUTOPREFIXER = 'off';
+  });
+
+  afterAll(() => {
+    delete process.env.AUTOPREFIXER;
+  });
+
+  const transform = (code: string, opts: TransformOptions = {}) =>
+    transformCode(code, { pretty: false, ...opts });
+
+  // Tests are based on those covered by vanilla-extract, credit goes to them :)
+  //
+  // https://github.com/vanilla-extract-css/vanilla-extract/blob/a623c1c65a543afcedb9feb30a7fe20452b99a95/packages/css/src/transformCss.test.ts#L639
+
+  it('should handle blank content', () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const ListItem = styled.div({
+        content: '',
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    expect(actual).toContain('._1sb2b3bt{content:""}');
+  });
+
+  it('should handle blank content (variant #1)', () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const ListItem = styled.div({
+        content: \`\`,
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    expect(actual).toContain('._1sb2b3bt{content:""}');
+  });
+
+  it('should handle blank content (variant #2)', () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const hello = '';
+      const ListItem = styled.div({
+        content: \`\${hello}\`,
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    expect(actual).toContain('._1sb2b3bt{content:""}');
+  });
+
+  it('should handle blank content (variant #2)', () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const hello = 'this is a string';
+      const ListItem = styled.div({
+        content: hello,
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    expect(actual).toContain('._1sb21icm{content:"this is a string"}');
+  });
+
+  it('should add quotes to custom content values', () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const ListItem = styled.div({
+        content: 'hello',
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    expect(actual).toContain('._1sb21e8g{content:"hello"}');
+  });
+
+  it('should not add quotes if they exist already', () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const ListItem = styled.div({
+        content: "'hello'",
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    expect(actual).toContain("._1sb25hbz{content:'hello'}");
+  });
+
+  it('should not add quotes if they exist already (variant)', () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const ListItem = styled.div({
+        content: '"hello"',
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    expect(actual).toContain('._1sb21e8g{content:"hello"}');
+  });
+
+  it("should not add quotes to content values that shouldn't accept them", () => {
+    const code = `
+      import { styled } from '@compiled/react';
+
+      const ListItem = styled.div({
+        '._01 &': { content: 'none' },
+        '._02 &': { content: 'url("http://www.example.com/test.png")' },
+        '._03 &': { content: 'linear-gradient(#e66465, #9198e5)' },
+        '._04 &': {
+          content: 'image-set("image1x.png" 1x, "image2x.png" 2x)',
+        },
+        '._05 &': {
+          content:
+            'url("http://www.example.com/test.png") / "This is the alt text"',
+        },
+        '._06 &': { content: '"prefix"' },
+        '._07 &': { content: 'counter(chapter_counter)' },
+        '._08 &': { content: 'counter(chapter_counter, upper-roman)' },
+        '._09 &': { content: 'counters(section_counter, ".")' },
+        '._10 &': {
+          content:
+            'counters(section_counter, ".", decimal-leading-zero)',
+        },
+        '._11 &': { content: 'attr(value string)' },
+        '._12 &': { content: 'open-quote' },
+        '._13 &': { content: 'close-quote' },
+        '._14 &': { content: 'no-open-quote' },
+        '._15 &': { content: 'no-close-quote' },
+        '._16 &': { content: 'open-quote counter(chapter_counter)' },
+        '._17 &': { content: 'inherit' },
+        '._18 &': { content: 'initial' },
+        '._19 &': { content: 'revert' },
+        '._20 &': { content: 'unset' },
+      });
+    `;
+
+    const actual = transform(code, { pretty: true });
+    const expectedStrings = [
+      '._20 ._dqocn7od{content:unset}',
+      '._19 ._kyq719ly{content:revert}',
+      '._18 ._ox6v18uv{content:initial}',
+      '._17 ._1do11kw7{content:inherit}',
+      '._16 ._17yjbbkt{content:open-quote counter(chapter_counter)}',
+      '._15 ._13gv16xt{content:no-close-quote}',
+      '._14 ._1gw4qmeg{content:no-open-quote}',
+      '._13 ._1erv1lzr{content:close-quote}',
+      '._12 ._yz5n12u0{content:open-quote}',
+      '._11 ._1sv1f7m1{content:attr(value string)}',
+      '._10 ._11jd1td3{content:counters(section_counter,".",decimal-leading-zero)}',
+      '._09 ._1vjjgvpy{content:counters(section_counter,".")}',
+      '._08 ._tc0r17sh{content:counter(chapter_counter,upper-roman)}',
+      '._07 ._1g4mlfyt{content:counter(chapter_counter)}',
+      '._06 ._4g5v1dlo{content:"prefix"}',
+      '._05 ._10o677hy{content:url("http://www.example.com/test.png") /"This is the alt text"}',
+      '._04 ._124v19iq{content:image-set("image1x.png" 1x,"image2x.png" 2x)}',
+      '._03 ._qi2v1f55{content:linear-gradient(#e66465,#9198e5)}',
+      '._02 ._1gdz1dgq{content:url("http://www.example.com/test.png")}',
+      '._01 ._1sagglyw{content:none}',
+    ];
+
+    for (const expected of expectedStrings) {
+      expect(actual).toContain(expected);
+    }
+  });
+});
diff --git a/packages/babel-plugin/src/utils/css-builders.ts b/packages/babel-plugin/src/utils/css-builders.ts
index ced98d5bc..30a450cc7 100644
--- a/packages/babel-plugin/src/utils/css-builders.ts
+++ b/packages/babel-plugin/src/utils/css-builders.ts
@@ -56,16 +56,25 @@ const findBindingIdentifier = (
 };
 
 /**
- * Will normalize the value of a `content` CSS property to ensure it has quotations around it.
- * This is done to replicate both how Styled Components behaves,
- * while not breaking how Emotion handles it.
+ * Will normalize the value of a `content` CSS property to ensure it has quotations around it,
+ * but only when we reasonably think that they were intended. For example, url(...) and counter(...)
+ * will NOT have quotes added around them.
  */
 const normalizeContentValue = (value: string) => {
-  if (value.charAt(0) !== '"' && value.charAt(0) !== "'") {
-    return `"${value}"`;
+  // Adapted from vanilla-extract's handling of the `content` key
+  // https://github.com/vanilla-extract-css/vanilla-extract/blob/a623c1c65a543afcedb9feb30a7fe20452b99a95/packages/css/src/transformCss.ts#L266
+  const contentValuePattern =
+    /^([A-Za-z\-]+\([^]*|[^]*-quote|inherit|initial|none|normal|revert|unset)(\s|$)/;
+
+  if (!value) {
+    return `""`;
+  }
+
+  if (value.includes('"') || value.includes("'") || contentValuePattern.test(value)) {
+    return value;
   }
 
-  return value;
+  return `"${value}"`;
 };
 
 /**