diff --git a/apps/server/src/routes/suggestions/generate-suggestions.ts b/apps/server/src/routes/suggestions/generate-suggestions.ts
index 908ea724..22855a89 100644
--- a/apps/server/src/routes/suggestions/generate-suggestions.ts
+++ b/apps/server/src/routes/suggestions/generate-suggestions.ts
@@ -289,11 +289,10 @@ ${JSON.stringify(suggestionsSchema, null, 2)}`;
         })),
       });
     } else {
-      // Fallback: try to parse from text (for backwards compatibility)
+      // Fallback: try to parse from text using multiple strategies
       logger.warn('No structured output received, attempting to parse from text');
-      const jsonMatch = responseText.match(/\{[\s\S]*"suggestions"[\s\S]*\}/);
-      if (jsonMatch) {
-        const parsed = JSON.parse(jsonMatch[0]);
+      const parsed = extractSuggestionsJson(responseText);
+      if (parsed && parsed.suggestions) {
         events.emit('suggestions:event', {
           type: 'suggestions_complete',
           suggestions: parsed.suggestions.map((s: Record<string, unknown>, i: number) => ({
@@ -323,3 +322,99 @@ ${JSON.stringify(suggestionsSchema, null, 2)}`;
     });
   }
 }
+
+/**
+ * Extract suggestions JSON from response text using multiple strategies.
+ * Handles various formats: markdown code blocks, raw JSON, etc.
+ */
+function extractSuggestionsJson(
+  responseText: string
+): { suggestions: Array<Record<string, unknown>> } | null {
+  const strategies = [
+    // Strategy 1: JSON in ```json code block
+    () => {
+      const match = responseText.match(/```json\s*([\s\S]*?)```/);
+      if (match) {
+        return JSON.parse(match[1].trim());
+      }
+      return null;
+    },
+    // Strategy 2: JSON in ``` code block (no language specified)
+    () => {
+      const match = responseText.match(/```\s*([\s\S]*?)```/);
+      if (match) {
+        const content = match[1].trim();
+        if (content.startsWith('{') && content.includes('"suggestions"')) {
+          return JSON.parse(content);
+        }
+      }
+      return null;
+    },
+    // Strategy 3: Find JSON object containing "suggestions" array
+    () => {
+      // Find the start of the JSON object
+      const startIdx = responseText.indexOf('{"suggestions"');
+      if (startIdx === -1) return null;
+
+      // Find matching closing brace by counting brackets
+      let depth = 0;
+      let endIdx = -1;
+      for (let i = startIdx; i < responseText.length; i++) {
+        if (responseText[i] === '{') depth++;
+        if (responseText[i] === '}') {
+          depth--;
+          if (depth === 0) {
+            endIdx = i + 1;
+            break;
+          }
+        }
+      }
+
+      if (endIdx > startIdx) {
+        return JSON.parse(responseText.slice(startIdx, endIdx));
+      }
+      return null;
+    },
+    // Strategy 4: Find any JSON object with suggestions
+    () => {
+      const startIdx = responseText.indexOf('{');
+      if (startIdx === -1) return null;
+
+      // Find matching closing brace
+      let depth = 0;
+      let endIdx = -1;
+      for (let i = startIdx; i < responseText.length; i++) {
+        if (responseText[i] === '{') depth++;
+        if (responseText[i] === '}') {
+          depth--;
+          if (depth === 0) {
+            endIdx = i + 1;
+            break;
+          }
+        }
+      }
+
+      if (endIdx > startIdx) {
+        const parsed = JSON.parse(responseText.slice(startIdx, endIdx));
+        if (parsed.suggestions && Array.isArray(parsed.suggestions)) {
+          return parsed;
+        }
+      }
+      return null;
+    },
+  ];
+
+  for (const strategy of strategies) {
+    try {
+      const result = strategy();
+      if (result && result.suggestions && Array.isArray(result.suggestions)) {
+        logger.debug('Successfully extracted suggestions JSON');
+        return result;
+      }
+    } catch {
+      // Strategy failed, try next
+    }
+  }
+
+  return null;
+}