diff --git a/src/components/AnalysisPlayground.tsx b/src/components/AnalysisPlayground.tsx
index 0701879..b2428b1 100644
--- a/src/components/AnalysisPlayground.tsx
+++ b/src/components/AnalysisPlayground.tsx
@@ -1,5 +1,5 @@
 import { useState, useEffect } from "react";
-import { cadenceApi } from "@/lib/cadenceApi";
+import { cadenceApi, parseAnalysisError } from "@/lib/cadenceApi";
 import {
   useStreamingAnalysis,
   type StreamStatus,
@@ -420,19 +420,57 @@ export function AnalysisPlayground() {
 
           {/* ---- Error ---- */}
           {stream.error && (
-            <motion.div
-              initial={{ opacity: 0, y: -8 }}
-              animate={{ opacity: 1, y: 0 }}
-              className="p-4 rounded-lg bg-red-500/5 border border-red-500/20 flex items-start gap-3"
-            >
-              <AlertCircle className="w-5 h-5 text-red-400 shrink-0 mt-0.5" />
-              <div>
-                <p className="text-sm font-medium text-red-300 mb-1">
-                  Analysis Failed
-                </p>
-                <p className="text-sm text-red-200/80">{stream.error}</p>
-              </div>
-            </motion.div>
+            (() => {
+              const parsedError = parseAnalysisError(stream.error);
+              return (
+                <motion.div
+                  initial={{ opacity: 0, y: -8 }}
+                  animate={{ opacity: 1, y: 0 }}
+                  className="p-4 rounded-lg bg-red-500/5 border border-red-500/20"
+                >
+                  <div className="flex items-start gap-3">
+                    <AlertCircle className="w-5 h-5 text-red-400 shrink-0 mt-0.5" />
+                    <div className="flex-1">
+                      <p className="text-sm font-semibold text-red-300 mb-1">
+                        {parsedError.title}
+                      </p>
+                      <p className="text-sm text-red-200/80 mb-2">
+                        {parsedError.message}
+                      </p>
+                      {parsedError.suggestion && (
+                        <p className="text-xs text-red-200/60 mb-3 italic">
+                          💡 {parsedError.suggestion}
+                        </p>
+                      )}
+                      <div className="flex gap-2">
+                        {parsedError.isRetryable && (
+                          <button
+                            onClick={() => {
+                              if (stream.analysisType && stream.targetUrl) {
+                                actions.startAnalysis(
+                                  stream.analysisType,
+                                  stream.targetUrl
+                                );
+                              }
+                            }}
+                            className="flex items-center gap-2 px-3 py-1.5 rounded-lg bg-red-500/20 border border-red-500/30 text-red-300 text-xs font-medium hover:bg-red-500/30 hover:text-red-200 transition-colors"
+                          >
+                            <RotateCcw className="w-3.5 h-3.5" />
+                            Retry
+                          </button>
+                        )}
+                        <button
+                          onClick={handleReset}
+                          className="flex items-center gap-2 px-3 py-1.5 rounded-lg bg-white/5 border border-white/10 text-white/70 text-xs font-medium hover:bg-white/10 hover:text-white transition-colors"
+                        >
+                          Try Different URL
+                        </button>
+                      </div>
+                    </div>
+                  </div>
+                </motion.div>
+              );
+            })()
           )}
 
           {/* ---- Live detection feed ---- */}
diff --git a/src/lib/cadenceApi.ts b/src/lib/cadenceApi.ts
index d2c1e85..f41ffe2 100644
--- a/src/lib/cadenceApi.ts
+++ b/src/lib/cadenceApi.ts
@@ -393,5 +393,106 @@ class CadenceAPI {
   }
 }
 
+// ---- Error message parser for user-friendly explanations ---- //
+
+export interface ParsedError {
+  title: string;
+  message: string;
+  suggestion?: string;
+  isRetryable: boolean;
+}
+
+export function parseAnalysisError(errorText: string): ParsedError {
+  const lower = errorText.toLowerCase();
+
+  // Bot protection / 403 Forbidden
+  if (lower.includes("403") || lower.includes("forbidden")) {
+    return {
+      title: "Website Blocked Analysis",
+      message:
+        "The website appears to have bot protection enabled (Cloudflare, WAF, or similar) that prevented analysis.",
+      suggestion:
+        "Try analyzing a different website, or check if the site is publicly accessible without special headers.",
+      isRetryable: false,
+    };
+  }
+
+  // 404 Not Found
+  if (lower.includes("404") || lower.includes("not found")) {
+    return {
+      title: "Website Not Found",
+      message: "The URL could not be reached or no longer exists.",
+      suggestion: "Verify the URL is correct and the website is online.",
+      isRetryable: true,
+    };
+  }
+
+  // Connection timeout
+  if (lower.includes("timeout") || lower.includes("timed out")) {
+    return {
+      title: "Connection Timeout",
+      message: "The request took too long and was cancelled.",
+      suggestion: "The website may be slow or unresponsive. Try again in a moment.",
+      isRetryable: true,
+    };
+  }
+
+  // DNS / Network errors
+  if (
+    lower.includes("dns") ||
+    lower.includes("net::") ||
+    lower.includes("econnrefused") ||
+    lower.includes("enotfound")
+  ) {
+    return {
+      title: "Network Error",
+      message: "Could not connect to the website due to a network issue.",
+      suggestion:
+        "Check if the domain name is correct and the website is online.",
+      isRetryable: true,
+    };
+  }
+
+  // TLS / SSL errors
+  if (lower.includes("ssl") || lower.includes("certificate") || lower.includes("tls")) {
+    return {
+      title: "SSL/Certificate Error",
+      message: "The website has an SSL certificate issue.",
+      suggestion: "The website's SSL certificate may be invalid or expired.",
+      isRetryable: false,
+    };
+  }
+
+  // Rate limiting
+  if (lower.includes("rate limit") || lower.includes("429")) {
+    return {
+      title: "Rate Limited",
+      message: "Too many requests were sent too quickly.",
+      suggestion: "Please wait a moment before trying again.",
+      isRetryable: true,
+    };
+  }
+
+  // Generic fetch errors
+  if (lower.includes("failed to fetch")) {
+    return {
+      title: "Failed to Fetch",
+      message:
+        "Could not fetch the website. This may be due to network issues or website protection.",
+      suggestion:
+        "Check your internet connection or try analyzing a different website.",
+      isRetryable: true,
+    };
+  }
+
+  // Default fallback
+  return {
+    title: "Analysis Failed",
+    message: errorText || "An unknown error occurred during analysis.",
+    suggestion: "Please try again or contact support if the issue persists.",
+    isRetryable: true,
+  };
+}
+
 // Export singleton instance
 export const cadenceApi = new CadenceAPI();