diff --git a/cli/src/osf.ts b/cli/src/osf.ts
index 91ecb7d..b9f283d 100644
--- a/cli/src/osf.ts
+++ b/cli/src/osf.ts
@@ -45,6 +45,35 @@ function extractText(run: TextRun): string {
   return '';
 }
 
+// Helper to convert TextRun objects to Markdown
+function textRunToMarkdown(run: TextRun): string {
+  if (typeof run === 'string') {
+    return run;
+  }
+  if ('type' in run) {
+    if (run.type === 'link') {
+      return `[${run.text}](${run.url})`;
+    }
+    if (run.type === 'image') {
+      return `![${run.alt}](${run.url})`;
+    }
+  }
+  if ('text' in run) {
+    let text = run.text;
+    if ((run as any).bold) {
+      text = `**${text}**`;
+    }
+    if ((run as any).italic) {
+      text = `*${text}*`;
+    }
+    if ((run as any).underline) {
+      text = `__${text}__`;
+    }
+    return text;
+  }
+  return '';
+}
+
 // Helper function to convert OSFValue to CellValue
 function toSpreadsheetData(data: Record<string, OSFValue> | undefined): SpreadsheetData {
   if (!data) return {};
@@ -600,12 +629,28 @@ function exportMarkdown(doc: OSFDocument): string {
           for (const block of slide.content) {
             if (block.type === 'unordered_list') {
               for (const item of block.items) {
-                const itemText = item.content.map(extractText).join('');
+                const itemText = item.content.map(textRunToMarkdown).join('');
                 out.push(`- ${itemText}`);
               }
+            } else if (block.type === 'ordered_list') {
+              block.items.forEach((item, idx) => {
+                const itemText = item.content.map(textRunToMarkdown).join('');
+                out.push(`${idx + 1}. ${itemText}`);
+              });
             } else if (block.type === 'paragraph') {
-              const paragraphText = block.content.map(extractText).join('');
+              const paragraphText = block.content.map(textRunToMarkdown).join('');
               out.push(paragraphText);
+            } else if (block.type === 'blockquote') {
+              for (const para of block.content) {
+                const quoteText = para.content.map(textRunToMarkdown).join('');
+                out.push(`> ${quoteText}`);
+              }
+            } else if (block.type === 'code') {
+              out.push(`\u0060\u0060\u0060${block.language || ''}`);
+              out.push(block.content);
+              out.push('\u0060\u0060\u0060');
+            } else if (block.type === 'image') {
+              out.push(`![${block.alt}](${block.url})`);
             }
           }
         }
diff --git a/cli/tests/cli.test.ts b/cli/tests/cli.test.ts
index b0f85a2..25c550a 100644
--- a/cli/tests/cli.test.ts
+++ b/cli/tests/cli.test.ts
@@ -60,6 +60,22 @@ const FORMULA_TEST_OSF = `@meta {
   formula (2,4): "=C1+C2";
 }`;
 
+const ADVANCED_OSF =
+  '@slide {\n' +
+  '  title: "Comprehensive Slide";\n\n' +
+  '  This is a paragraph with **bold**, *italic*, and __underlined__ text.\n\n' +
+  '  - Unordered item 1\n' +
+  '  - Unordered item 2\n\n' +
+  '  1. Ordered item 1\n' +
+  '  2. Ordered item 2\n\n' +
+  '  > This is a blockquote.\n\n' +
+  '  ```javascript\n' +
+  '  console.log("Hello, World!");\n' +
+  '  ```\n\n' +
+  '  ![An image alt text](https://example.com/image.png)\n\n' +
+  '  [A link to somewhere](https://example.com)\n' +
+  '}';
+
 const INVALID_OSF = `@meta {
   title: "Unclosed Block"
   // Missing closing brace`;
@@ -294,6 +310,27 @@ describe('OSF CLI', () => {
       expect(result).toContain('15 *(calc)*'); // (115-100)/100*100 = 15
     });
 
+    it('should export advanced content to Markdown', () => {
+      const advancedFile = join(TEST_FIXTURES_DIR, 'advanced.osf');
+      writeFileSync(advancedFile, ADVANCED_OSF, 'utf8');
+      try {
+        const result = execSync(`node "${CLI_PATH}" export "${advancedFile}"`, {
+          encoding: 'utf8',
+        });
+
+        expect(result).toContain('1. Ordered item 1');
+        expect(result).toContain('> This is a blockquote.');
+        expect(result).toContain('```javascript');
+        expect(result).toContain('console.log("Hello, World!");');
+        expect(result).toContain('![An image alt text](https://example.com/image.png)');
+        expect(result).toContain('[A link to somewhere](https://example.com)');
+      } finally {
+        if (existsSync(advancedFile)) {
+          unlinkSync(advancedFile);
+        }
+      }
+    });
+
     it('should export OSF with formulas to Markdown', () => {
       const formulaFile = join(TEST_FIXTURES_DIR, 'formula_test.osf');
       writeFileSync(formulaFile, FORMULA_TEST_OSF, 'utf8');