diff --git a/debugsyms/cmd/upload.go b/debugsyms/cmd/upload.go
index a8b8765..e54f243 100644
--- a/debugsyms/cmd/upload.go
+++ b/debugsyms/cmd/upload.go
@@ -44,7 +44,7 @@
 
 func (cmd *uploadCommand) SetFlags(f *flag.FlagSet) {
 	f.StringVar(&cmd.bucket, "bucket", "", "GCS bucket to upload symbols to")
-	f.DurationVar(&cmd.timeout, "timeout", 10*time.Minute, "timeout duration per upload")
+	f.DurationVar(&cmd.timeout, "timeout", 20*time.Minute, "timeout duration per upload")
 	f.IntVar(&cmd.j, "j", 500, "number of concurrent uploading routines")
 }
 
diff --git a/debugsyms/cmd/worker.go b/debugsyms/cmd/worker.go
index f97dd5d..44bf0b4 100644
--- a/debugsyms/cmd/worker.go
+++ b/debugsyms/cmd/worker.go
@@ -6,6 +6,7 @@
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"sync"
 	"time"
@@ -41,7 +42,11 @@
 				errs <- fmt.Errorf("job %s failed: %v", job.name, err)
 			}
 		case <-ctx.Done():
-			errs <- jobTimeout{job: job, timeout: timeout}
+			if errors.Is(ctx.Err(), context.DeadlineExceeded) {
+				errs <- jobTimeout{job: job, timeout: timeout}
+			} else {
+				errs <- fmt.Errorf("job %s was canceled", job.name)
+			}
 		}
 	}
 }