diff --git a/changelog.d/fixed-362-rewrite-image-paths.md b/changelog.d/fixed-362-rewrite-image-paths.md
new file mode 100644
index 00000000..145d3af4
--- /dev/null
+++ b/changelog.d/fixed-362-rewrite-image-paths.md
@@ -0,0 +1 @@
+- Fixed `rewriteRelativeImagePaths` so `../` image references resolve inside docs/content (instead of 403) and titled images (`![alt](img.png "Title")`) no longer 404.
diff --git a/src/__tests__/rewriteImagePaths.test.ts b/src/__tests__/rewriteImagePaths.test.ts
index 6add2b62..7927b290 100644
--- a/src/__tests__/rewriteImagePaths.test.ts
+++ b/src/__tests__/rewriteImagePaths.test.ts
@@ -73,4 +73,36 @@ describe("rewriteRelativeImagePaths", () => {
     const twice = rewriteRelativeImagePaths(once, "console");
     expect(twice).toBe(once);
   });
+
+  it("resolves ../ against baseDir", () => {
+    expect(
+      rewriteRelativeImagePaths("![logo](../images/logo.png)", "hive/guides")
+    ).toBe("![logo](/docs-images/hive/images/logo.png)");
+  });
+
+  it("leaves ../ that escapes docs/content unchanged", () => {
+    const md = "![logo](../../../etc/logo.png)";
+    expect(rewriteRelativeImagePaths(md, "hive/guides")).toBe(md);
+    expect(rewriteRelativeImagePaths("![x](../x.png)", "")).toBe(
+      "![x](../x.png)"
+    );
+  });
+
+  it("preserves a double-quoted title", () => {
+    expect(
+      rewriteRelativeImagePaths('![logo](images/logo.png "Logo")', "hive")
+    ).toBe('![logo](/docs-images/hive/images/logo.png "Logo")');
+  });
+
+  it("preserves a single-quoted title", () => {
+    expect(
+      rewriteRelativeImagePaths("![logo](./images/logo.png 'Logo')", "hive")
+    ).toBe("![logo](/docs-images/hive/images/logo.png 'Logo')");
+  });
+
+  it("still rewrites a plain relative path without a title", () => {
+    expect(rewriteRelativeImagePaths("![a](images/a.png)", "")).toBe(
+      "![a](/docs-images/images/a.png)"
+    );
+  });
 });
diff --git a/src/lib/rewriteImagePaths.ts b/src/lib/rewriteImagePaths.ts
index a264793e..17d211d9 100644
--- a/src/lib/rewriteImagePaths.ts
+++ b/src/lib/rewriteImagePaths.ts
@@ -19,7 +19,11 @@ export function rewriteRelativeImagePaths(
   return content.replace(
     /!\[([^\]]*)\]\(([^)]+)\)/g,
     (match, alt: string, src: string) => {
-      const trimmed = src.trim();
+      const raw = src.trim();
+      // Split an optional CommonMark title (` "..."` or ` '...'`) off the destination.
+      const titleMatch = /^(\S+)(\s+(?:"[^"]*"|'[^']*'))$/.exec(raw);
+      const trimmed = titleMatch ? titleMatch[1] : raw;
+      const title = titleMatch ? titleMatch[2] : "";
       // Leave absolute URLs, absolute paths, data URIs, and anchor-only refs unchanged.
       if (
         trimmed.startsWith("/") ||
@@ -29,11 +33,23 @@ export function rewriteRelativeImagePaths(
       ) {
         return match;
       }
-      const normalised = trimmed.replace(/^\.\//, "");
-      const apiPath = baseDir
-        ? `/docs-images/${baseDir}/${normalised}`
-        : `/docs-images/${normalised}`;
-      return `![${alt}](${apiPath})`;
+      // Pure string normalisation (this module may run in the browser).
+      const segments: string[] = [];
+      const parts = [
+        ...(baseDir ? baseDir.split("/") : []),
+        ...trimmed.split("/"),
+      ];
+      for (const part of parts) {
+        if (part === "" || part === ".") continue;
+        if (part === "..") {
+          // Escapes docs/content: leave the original reference unchanged.
+          if (segments.length === 0) return match;
+          segments.pop();
+        } else {
+          segments.push(part);
+        }
+      }
+      return `![${alt}](/docs-images/${segments.join("/")}${title})`;
     }
   );
 }