diff --git a/src/shadowbox/package.json b/src/shadowbox/package.json
index 3c3b82e5..5a5d4fea 100644
--- a/src/shadowbox/package.json
+++ b/src/shadowbox/package.json
@@ -1,7 +1,7 @@
 {
   "name": "outline-server",
   "private": true,
-  "version": "1.5.2",
+  "version": "1.5.3",
   "description": "Outline server",
   "main": "build/server/main.js",
   "author": "Outline",
diff --git a/third_party/outline-ss-server/METADATA b/third_party/outline-ss-server/METADATA
index 5ceb50fb..73741b3a 100644
--- a/third_party/outline-ss-server/METADATA
+++ b/third_party/outline-ss-server/METADATA
@@ -8,8 +8,8 @@ third_party {
   }
   url {
     type: ARCHIVE
-    value: "https://github.com/Jigsaw-Code/outline-ss-server/releases/tag/v1.3.2"
+    value: "https://github.com/Jigsaw-Code/outline-ss-server/releases/tag/v1.3.3"
   }
-  version: "1.3.2"
-  last_upgrade_date { year: 2020 month: 11 day: 3 }
+  version: "1.3.3"
+  last_upgrade_date { year: 2020 month: 11 day: 6 }
 }
diff --git a/third_party/outline-ss-server/linux/outline-ss-server b/third_party/outline-ss-server/linux/outline-ss-server
index 456e13fb..7db0168d 100755
Binary files a/third_party/outline-ss-server/linux/outline-ss-server and b/third_party/outline-ss-server/linux/outline-ss-server differ
diff --git a/third_party/outline-ss-server/macos/outline-ss-server b/third_party/outline-ss-server/macos/outline-ss-server
index 30588ee5..0752e631 100755
Binary files a/third_party/outline-ss-server/macos/outline-ss-server and b/third_party/outline-ss-server/macos/outline-ss-server differ