diff --git a/server/shared/image-attachments.ts b/server/shared/image-attachments.ts
index 752be34e..7a160c33 100644
--- a/server/shared/image-attachments.ts
+++ b/server/shared/image-attachments.ts
@@ -82,12 +82,30 @@ export function toPosixPath(value: string): string {
   return value.replace(/\\/g, '/');
 }
 
-/** Resolves a project-relative image path against the run's working directory. */
+/** Resolves an allowed image path against the run's working directory. */
 export function resolveImageAbsolutePath(cwd: string | undefined, imagePath: string): string {
+  const baseDir = path.resolve(cwd || process.cwd());
+  const globalAssetsDir = path.resolve(getGlobalImageAssetsDir());
+
   if (path.isAbsolute(imagePath)) {
-    return imagePath;
+    const absoluteInput = path.resolve(imagePath);
+    if (isPathInsideDirectory(absoluteInput, globalAssetsDir)) {
+      return absoluteInput;
+    }
   }
-  return path.resolve(cwd || process.cwd(), imagePath);
+
+  const resolved = path.resolve(baseDir, imagePath);
+  const relative = path.relative(baseDir, resolved);
+  const escapesBase =
+    relative === '..' ||
+    relative.startsWith(`..${path.sep}`) ||
+    path.isAbsolute(relative);
+
+  if (escapesBase) {
+    throw new Error(`Image path escapes working directory: ${imagePath}`);
+  }
+
+  return resolved;
 }
 
 function isPathInsideDirectory(candidate: string, directory: string): boolean {
@@ -196,6 +214,16 @@ const IMAGES_INPUT_ENTRY_PATTERN = /\d+\.\s+(.+?)(?=\s+\d+\.\s+|\s*$)/g;
 
 const ORIGINAL_NAME_SUFFIX_PATTERN = /\(original name: ([^)]*)\)\s*$/;
 
+function tryResolveImageAbsolutePath(cwd: string | undefined, descriptor: ImageAttachmentDescriptor): string | null {
+  try {
+    return resolveImageAbsolutePath(cwd, descriptor.path);
+  } catch (error) {
+    const message = error instanceof Error ? error.message : String(error);
+    console.warn(`[Images] Refusing image outside allowed roots: ${message}`);
+    return null;
+  }
+}
+
 function parseNumberedImageEntries(inner: string): ParsedImageAttachment[] {
   const attachments: ParsedImageAttachment[] = [];
   for (const entryMatch of inner.matchAll(IMAGES_INPUT_ENTRY_PATTERN)) {
@@ -282,7 +310,11 @@ export async function buildClaudeUserContent(
       continue;
     }
 
-    const resolvedPath = resolveImageAbsolutePath(cwd, descriptor.path);
+    const resolvedPath = tryResolveImageAbsolutePath(cwd, descriptor);
+    if (!resolvedPath) {
+      continue;
+    }
+
     if (!isAllowedImageSourcePath(resolvedPath, cwd)) {
       console.warn(`[Images] Refusing to read image outside allowed roots: ${descriptor.path}`);
       continue;
@@ -325,7 +357,11 @@ type CodexInputItem =
 export function buildCodexInputItems(prompt: string, images: unknown, cwd?: string): CodexInputItem[] {
   const items: CodexInputItem[] = [{ type: 'text', text: prompt }];
   for (const descriptor of normalizeImageDescriptors(images)) {
-    const resolvedPath = resolveImageAbsolutePath(cwd, descriptor.path);
+    const resolvedPath = tryResolveImageAbsolutePath(cwd, descriptor);
+    if (!resolvedPath) {
+      continue;
+    }
+
     if (!isAllowedImageSourcePath(resolvedPath, cwd)) {
       // Same trust boundary as buildClaudeUserContent — the Codex runtime
       // reads this file, so it must stay within the allowed roots.