diff --git a/src/app/api/chat/route.ts b/src/app/api/chat/route.ts
index b1af3279..7d381f15 100644
--- a/src/app/api/chat/route.ts
+++ b/src/app/api/chat/route.ts
@@ -142,7 +142,9 @@ CRITICAL INSTRUCTIONS FOR WORKSPACE CURATION:
    - Use \`updateNote\` tool for notes
    - Use \`updateFlashcards\` tool for flashcard sets
    - Use \`updateQuiz\` tool for quizzes
-2. **Be thorough but focused** - Provide a solid foundation for understanding the topic without being overwhelming.
+2. **Be thorough and exhaustive** - Provide deep, academic, and comprehensive coverage. Notes must be detailed and extensive. Avoid summaries.
+   - **Structure**: Use H2/H3 headers, bullet points, and **bold** text for readability.
+   - **Math**: Use block math \`$$...$$\` for equations.
 3. **Do NOT ask the user questions** - This is an automated initialization, proceed directly with updating the workspace.
 
 QUALITY GUIDELINES FOR CONTENT:
@@ -185,7 +187,18 @@ When creating/updating notes with research:
 Rules:
 - Use chunk.web.uri exactly as provided (even redirect URLs)
 - Never make up or hallucinate URLs
-- Include article dates in responses when available`);
+- Include article dates in responses when available
+
+CONTENT GENERATION RULE:
+When creating or updating notes, your goal is to be **exhaustive** and **well-structured**.
+- **Length**: Write long, detailed paragraphs. Never trade depth for brevity.
+- **Headers**: Use H2 (\`##\`) and H3 (\`###\`) to organize sections.
+- **Formatting**: **Bold** key terms and defined concepts.
+- **Lists**: Use bullet points for steps, features, or lists to improve readability.
+- **Math**: Use block math (\`$$...$$\`) for important equations so they render centered. **DO NOT use quadruple dollar signs (\`$$$$\`).**
+- **Callouts**: Use blockquotes (\`>\`) for key takeaways or definitions.
+- Include code examples and historical context where relevant.
+`);
 
 
   // Add file detection hint if file URLs are present
diff --git a/src/components/assistant-ui/markdown-text.tsx b/src/components/assistant-ui/markdown-text.tsx
index a2392037..aa27371c 100644
--- a/src/components/assistant-ui/markdown-text.tsx
+++ b/src/components/assistant-ui/markdown-text.tsx
@@ -159,6 +159,8 @@ export const MarkdownText = memo(MarkdownTextImpl);
 
 function normalizeCustomMathTags(input: string): string {
   return (input
+    // Fix quadruple dollar signs (often generated by AI) to double dollar signs
+    .replace(/\${4}/g, '$$')
     // Convert \( ... \) to $$...$$ (inline math) - streamdown uses $$ for both, inline has no newlines
     .replace(/\\{1,2}\(([\s\S]*?)\\{1,2}\)/g, (_, content) => `$$${content.trim()}$$`)
     // Convert \[ ... \] to $$...$$ (block math) - streamdown needs newlines for block triggers
diff --git a/src/components/assistant-ui/standalone-markdown.tsx b/src/components/assistant-ui/standalone-markdown.tsx
index d4619035..3b725625 100644
--- a/src/components/assistant-ui/standalone-markdown.tsx
+++ b/src/components/assistant-ui/standalone-markdown.tsx
@@ -59,6 +59,8 @@ const CodeHeader: FC<{ language?: string; code: string }> = ({ language, code })
 function normalizeCustomMathTags(input: string): string {
   return (
     input
+      // Fix quadruple dollar signs (often generated by AI) to double dollar signs
+      .replace(/\${4}/g, '$$')
       // Convert [/math]...[/math] to $$...$$ (legacy block math format)
       .replace(/\[\/math\]([\s\S]*?)\[\/math\]/g, (_, content) => `$$${content.trim()}$$`)
       // Convert [/inline]...[/inline] to $...$ (legacy inline format - ReactMarkdown uses $ for inline)
@@ -67,8 +69,8 @@ function normalizeCustomMathTags(input: string): string {
       .replace(/\\{1,2}\(([\s\S]*?)\\{1,2}\)/g, (_, content) => `$${content.trim()}$`)
       // Convert \[ ... \] to $$...$$ (LaTeX block math)
       .replace(/\\{1,2}\[([\s\S]*?)\\{1,2}\]/g, (_, content) => `$$${content.trim()}$$`)
-      // Note: We DON'T convert $...$ to $$ here because ReactMarkdown with remark-math expects
-      // single dollar signs for inline math and double dollar signs for block math
+    // Note: We DON'T convert $...$ to $$ here because ReactMarkdown with remark-math expects
+    // single dollar signs for inline math and double dollar signs for block math
   );
 }
 
diff --git a/src/lib/ai/tools/workspace-tools.ts b/src/lib/ai/tools/workspace-tools.ts
index 13a979ec..50881d04 100644
--- a/src/lib/ai/tools/workspace-tools.ts
+++ b/src/lib/ai/tools/workspace-tools.ts
@@ -22,7 +22,7 @@ export function createNoteTool(ctx: WorkspaceToolContext) {
         inputSchema: zodSchema(
             z.object({
                 title: z.string().describe("The title of the note card"),
-                content: z.string().describe("The markdown body content. DO NOT repeat title in content. Start with subheadings/text. No Mermaid. Use $$...$$ for ALL math (both inline and block). Single $ is for currency only."),
+                content: z.string().describe("The markdown body content. Must be detailed, comprehensive, and long-form. **Structure with H2/H3 headers, bullet points, and bold key terms**. Use block math $$...$$ for equations (do not use $$$$). Minimum 3-4 paragraphs."),
                 sources: z.array(
                     z.object({
                         title: z.string().describe("Title of the source page"),
@@ -76,7 +76,7 @@ export function createUpdateNoteTool(ctx: WorkspaceToolContext) {
         inputSchema: zodSchema(
             z.object({
                 noteName: z.string().describe("The name of the note to update (will be matched using fuzzy search)"),
-                content: z.string().describe("The full note body ONLY (do not include the title as a header). Use $$...$$ for ALL math."),
+                content: z.string().describe("The full note body ONLY (do not include the title as a header). Must be detailed, comprehensive, and long-form. **Structure with H2/H3 headers, bullet points, and bold key terms**. Use block math $$...$$ for equations (do not use $$$$)."),
                 title: z.string().optional().describe("New title for the note. If not provided, the existing title will be preserved."),
                 sources: z.array(
                     z.object({