diff --git a/lib/object-storage-web/src/use-upload.ts b/lib/object-storage-web/src/use-upload.ts
index 7ec850e4..7808fa66 100644
--- a/lib/object-storage-web/src/use-upload.ts
+++ b/lib/object-storage-web/src/use-upload.ts
@@ -75,7 +75,14 @@ export function useUpload(options: UseUploadOptions = {}) {
 
       if (!response.ok) {
         const errorData = await response.json().catch(() => ({}));
-        throw new Error(errorData.error || "Failed to get upload URL");
+        const serverMsg =
+          (typeof errorData?.error === "string" && errorData.error) ||
+          (typeof errorData?.message === "string" && errorData.message) ||
+          "";
+        const detail = serverMsg
+          ? `${serverMsg} (HTTP ${response.status})`
+          : `HTTP ${response.status} ${response.statusText || ""}`.trim();
+        throw new Error(`Failed to get upload URL: ${detail}`);
       }
 
       return response.json();
@@ -85,16 +92,39 @@ export function useUpload(options: UseUploadOptions = {}) {
 
   const uploadToPresignedUrl = useCallback(
     async (file: File, uploadURL: string): Promise<void> => {
-      const response = await fetch(uploadURL, {
-        method: "PUT",
-        body: file,
-        headers: {
-          "Content-Type": file.type || "application/octet-stream",
-        },
-      });
+      let response: Response;
+      try {
+        response = await fetch(uploadURL, {
+          method: "PUT",
+          body: file,
+          headers: {
+            "Content-Type": file.type || "application/octet-stream",
+          },
+        });
+      } catch (err) {
+        // Network-level failure (CORS, DNS, unreachable host). This is
+        // the typical symptom when PUBLIC_BASE_URL on the server points
+        // at an origin the browser can't actually reach (e.g. localhost
+        // while the user is on Tailscale).
+        const msg = err instanceof Error ? err.message : String(err);
+        let host = "";
+        try {
+          host = new URL(uploadURL).host;
+        } catch {
+          /* ignore */
+        }
+        throw new Error(
+          `Failed to upload file to storage: network error reaching ${host || "the storage endpoint"} — ${msg}`,
+        );
+      }
 
       if (!response.ok) {
-        throw new Error("Failed to upload file to storage");
+        const bodyText = await response.text().catch(() => "");
+        const snippet = bodyText.slice(0, 200).trim();
+        const detail = snippet
+          ? `${snippet} (HTTP ${response.status})`
+          : `HTTP ${response.status} ${response.statusText || ""}`.trim();
+        throw new Error(`Failed to upload file to storage: ${detail}`);
       }
     },
     []