diff --git a/frontend/src/lib/api.ts b/frontend/src/lib/api.ts
index f3de474..5bcef38 100644
--- a/frontend/src/lib/api.ts
+++ b/frontend/src/lib/api.ts
@@ -149,6 +149,7 @@ class ApiClient {
       headers: {
         'Content-Type': 'multipart/form-data',
       },
+      timeout: 0, // No timeout for video uploads (can be large files)
       onUploadProgress: onUploadProgress ? (progressEvent) => {
         if (progressEvent.total) {
           onUploadProgress({
diff --git a/frontend/src/routes/jobs/NewJob.tsx b/frontend/src/routes/jobs/NewJob.tsx
index ef417e8..196685a 100644
--- a/frontend/src/routes/jobs/NewJob.tsx
+++ b/frontend/src/routes/jobs/NewJob.tsx
@@ -89,7 +89,37 @@ export function NewJob() {
       }, 3000);
     } catch (error) {
       console.error('Job creation failed:', error);
-      toast.toastOnly.error('Failed to create job. Please check your file and try again.');
+
+      // Provide specific error messages based on error type
+      const err = error as any;
+      let errorMessage = 'Failed to create job. ';
+
+      if (err.code === 'ERR_NETWORK') {
+        errorMessage += 'Network error - cannot reach server. Please check your connection.';
+      } else if (err.code === 'ECONNABORTED' || err.message?.includes('timeout')) {
+        errorMessage += 'Upload timeout. Your file may be too large or connection too slow.';
+      } else if (err.response?.status === 413) {
+        errorMessage += 'File is too large. Maximum file size is 500MB.';
+      } else if (err.response?.status === 400) {
+        const detail = err.response?.data?.detail;
+        if (detail?.includes('video')) {
+          errorMessage += 'Invalid file type. Please upload a video file (MP4, MOV, etc).';
+        } else {
+          errorMessage += detail || 'Invalid request data. Please check all fields.';
+        }
+      } else if (err.response?.status === 401) {
+        errorMessage += 'Session expired. Please log in again.';
+      } else if (err.response?.status === 403) {
+        errorMessage += 'You do not have permission to create jobs.';
+      } else if (err.response?.status === 500) {
+        errorMessage += 'Server error. Please try again or contact support.';
+      } else if (err.message) {
+        errorMessage += err.message;
+      } else {
+        errorMessage += 'Unknown error. Please try again.';
+      }
+
+      toast.toastOnly.error(errorMessage);
       setUploadProgress(0);
     }
   };