diff --git a/astro/package.json b/astro/package.json
index b6a46108..0499951f 100644
--- a/astro/package.json
+++ b/astro/package.json
@@ -33,6 +33,8 @@
     "astro": "^6.1.0",
     "astro-opengraph-images": "^1.14.3",
     "astro-redirect-from": "^1.3.5",
+    "globby": "^16.1.1",
+    "gray-matter": "^4.0.3",
     "astro-rehype-relative-markdown-links": "^0.19.0",
     "hast-util-to-text": "^4.0.2",
     "jsdom": "^29.0.2",
diff --git a/astro/src/plugins/static-redirects.ts b/astro/src/plugins/static-redirects.ts
index c08758a3..4a8b4d25 100644
--- a/astro/src/plugins/static-redirects.ts
+++ b/astro/src/plugins/static-redirects.ts
@@ -2,8 +2,10 @@ import url from "node:url";
 import type { AstroConfig, AstroIntegrationLogger } from "astro";
 import path from "node:path";
 import fs from "node:fs/promises";
+import { globby } from "globby";
+import matter from "gray-matter";
 
-const redirectMap: Record<string, string> = {};
+const redirectMap = new Map<string, string>();
 
 export async function configurePlugin(hookOptions: any) {
   const buildOutput: string = hookOptions.buildOutput;
@@ -26,41 +28,186 @@ export async function configurePlugin(hookOptions: any) {
 
   // Build redirect map
   logger.info("Generating static redirects file...");
-  Object.keys(redirects).forEach((from) => {
-    const redirect = redirects[from];
+  for (const [from, redirect] of Object.entries(redirects)) {
     const destination =
       typeof redirect === "string" ? redirect : redirect.destination;
 
     // Normalize: strip trailing slash from source for consistent matching
     const normalizedFrom = from.endsWith("/") ? from.slice(0, -1) : from;
+
     // Ensure destination has trailing slash
     const normalizedTo = destination.endsWith("/")
       ? destination
       : destination + "/";
 
-    redirectMap[normalizedFrom] = normalizedTo;
+    redirectMap.set(normalizedFrom, normalizedTo);
+  }
+
+  const contentDir = path.join(
+    url.fileURLToPath(config.srcDir),
+    "content",
+    "docs",
+  );
+
+  // Detect duplicate redirect_from entries across content files.
+  // We cannot detect duplicates from config.redirects alone: astro-redirect-from
+  // builds a plain JS object from frontmatter, so when two files declare the same
+  // redirect_from path, the second silently overwrites the first before our hook
+  // ever runs. Scanning frontmatter directly is the only way to catch these.
+  await detectDuplicateRedirects(logger, contentDir);
+}
+
+/**
+ * Reads a file in chunks until the closing `---` of the YAML frontmatter block
+ * is found, then returns only those bytes. This avoids loading the full file
+ * body. The loop keeps reading until the delimiter is seen or EOF is reached.
+ */
+async function extractFrontmatterBlock(filePath: string): Promise<string> {
+  const CHUNK_SIZE = 4096;
+  const handle = await fs.open(filePath, "r");
+  try {
+    let accumulated = "";
+    let offset = 0;
+    let firstChunk = true;
+    // searchFrom tracks how far we've already scanned for the closing delimiter
+    // so each chunk addition only rescans the newly added bytes.
+    let searchFrom = 0;
+
+    while (true) {
+      const buf = Buffer.alloc(CHUNK_SIZE);
+      const { bytesRead } = await handle.read(buf, 0, CHUNK_SIZE, offset);
+      if (bytesRead === 0) break;
+
+      const chunk = buf.toString("utf-8", 0, bytesRead);
+      accumulated += chunk;
+      offset += bytesRead;
+
+      // After reading the first chunk, bail out early for files without frontmatter
+      if (firstChunk) {
+        firstChunk = false;
+        if (!accumulated.startsWith("---")) return "";
+        // Skip past the opening --- line before searching for the closing one
+        searchFrom = accumulated.indexOf("\n") + 1;
+      }
+
+      // Search for the closing --- delimiter starting where we left off
+      const closingIdx = accumulated.indexOf("\n---", searchFrom);
+      if (closingIdx !== -1) {
+        // Include the closing delimiter line in the returned block
+        const endIdx = accumulated.indexOf("\n", closingIdx + 1);
+        return endIdx === -1
+          ? accumulated.slice(0, closingIdx + 4)
+          : accumulated.slice(0, endIdx + 1);
+      }
+
+      // Advance searchFrom so the next iteration only scans the new chunk,
+      // minus a small overlap to avoid splitting a \n--- across chunk boundaries.
+      searchFrom = Math.max(searchFrom, accumulated.length - 4);
+
+      if (bytesRead < CHUNK_SIZE) break; // reached EOF before closing delimiter
+    }
+
+    // No closing --- found. gray-matter returns empty data for malformed
+    // frontmatter, so the caller's redirect_from check will safely skip this file.
+    return accumulated;
+  } finally {
+    await handle.close();
+  }
+}
+
+async function detectDuplicateRedirects(
+  logger: AstroIntegrationLogger,
+  contentDir: string,
+) {
+  const files = await globby("./**/*.{md,mdx}", {
+    cwd: contentDir,
+    gitignore: true,
   });
+
+  // Map each redirect source path to the list of files that claim it
+  const sourceToFiles = new Map<string, string[]>();
+
+  for (const file of files) {
+    const filePath = path.join(contentDir, file);
+
+    // Read only the frontmatter block, scanning until the closing --- delimiter
+    // regardless of how large the frontmatter may be.
+    const frontmatterBlock = await extractFrontmatterBlock(filePath);
+
+    if (!frontmatterBlock.includes("redirect_from")) continue;
+
+    const { data: frontmatter } = matter(frontmatterBlock);
+
+    if (!frontmatter?.redirect_from) continue;
+
+    const redirectFrom: string[] = Array.isArray(frontmatter.redirect_from)
+      ? frontmatter.redirect_from
+      : [frontmatter.redirect_from];
+
+    const normalizeRedirectSource = (source: string) => {
+      const trimmed = source.trim();
+      if (trimmed !== source) {
+        logger.warn(
+          `Trimmed whitespace from redirect_from entry in ${file}: ${JSON.stringify(source)} -> ${JSON.stringify(trimmed)}`,
+        );
+      }
+      return trimmed.endsWith("/") ? trimmed.slice(0, -1) : trimmed;
+    };
+
+    for (const source of redirectFrom) {
+      const normalized = normalizeRedirectSource(source);
+      const existing = sourceToFiles.get(normalized);
+      if (existing) {
+        existing.push(file);
+      } else {
+        sourceToFiles.set(normalized, [file]);
+      }
+    }
+  }
+
+  let duplicateCount = 0;
+  for (const [source, claimingFiles] of sourceToFiles) {
+    if (claimingFiles.length > 1) {
+      if (duplicateCount === 0) {
+        logger.error("Duplicate redirect_from entries detected:");
+      }
+      duplicateCount++;
+      logger.error(
+        `  "${source}" is claimed by ${claimingFiles.length} files: ${claimingFiles.join(", ")}`,
+      );
+    }
+  }
+
+  if (duplicateCount > 0) {
+    throw new Error(
+      `Build failed: ${duplicateCount} duplicate redirect_from source(s) detected. See log above for details.`,
+    );
+  }
 }
 
 export async function writeToOutput(hookOptions: any) {
   const outDir: string = hookOptions.dir;
   const logger: AstroIntegrationLogger = hookOptions.logger;
 
-  if (!Object.keys(redirectMap).length) {
+  if (redirectMap.size === 0) {
     logger.warn(
       `Skip generating static redirects file: no redirects were generated.`,
     );
     return;
   }
 
-  // Write redirects.json
   const jsonDestinationPath = path.join(
     url.fileURLToPath(outDir),
     "redirects.json",
   );
-  await fs.writeFile(jsonDestinationPath, JSON.stringify(redirectMap, null, 2));
+  await fs.writeFile(
+    jsonDestinationPath,
+    JSON.stringify(Object.fromEntries(redirectMap), null, 2),
+    "utf-8",
+  );
+
   logger.info(
-    `Generated ${Object.keys(redirectMap).length} redirects: ${jsonDestinationPath}`,
+    `Generated ${redirectMap.size} redirects: ${jsonDestinationPath}`,
   );
 }