diff --git a/.changeset/retry-backup-more.md b/.changeset/retry-backup-more.md
new file mode 100644
index 000000000..a57f27a47
--- /dev/null
+++ b/.changeset/retry-backup-more.md
@@ -0,0 +1,5 @@
+---
+"ggt": patch
+---
+
+Retry errors when backing up files on Windows more often.
diff --git a/src/services/filesync/filesync.ts b/src/services/filesync/filesync.ts
index 73eda1a50..1e2c29134 100644
--- a/src/services/filesync/filesync.ts
+++ b/src/services/filesync/filesync.ts
@@ -657,7 +657,9 @@ export class FileSync {
           }
         },
         {
-          retries: 2,
+          // windows tends to run into these issues way more often than
+          // mac/linux, so we retry more times
+          retries: config.windows ? 4 : 2,
           minTimeout: ms("100ms"),
           onFailedAttempt: (error) => {
             this.ctx.log.warn("failed to move file to backup", { error, currentPath, backupPath });