diff --git a/src/shadowbox/docker/Dockerfile b/src/shadowbox/docker/Dockerfile
index 936a5e09..7b249d40 100644
--- a/src/shadowbox/docker/Dockerfile
+++ b/src/shadowbox/docker/Dockerfile
@@ -39,7 +39,7 @@ FROM ${NODE_IMAGE}
 # Save metadata on the software versions we are using.
 LABEL shadowbox.node_version=12.16.3
 # Keep in sync with version in third_party/outline-ss-server
-LABEL shadowbox.outline-ss-server_version=1.1.4
+LABEL shadowbox.outline-ss-server_version=1.1.5
 
 ARG GITHUB_RELEASE
 LABEL shadowbox.github.release="${GITHUB_RELEASE}"
diff --git a/third_party/outline-ss-server/METADATA b/third_party/outline-ss-server/METADATA
index 0af83003..49699e6f 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/v1.1.4"
+    value: "https://github.com/Jigsaw-Code/outline-ss-server/releases/tag/v1.1.5"
   }
-  version: "1.1.4"
-  last_upgrade_date { year: 2020 month: 5 day: 29 }
+  version: "1.1.5"
+  last_upgrade_date { year: 2020 month: 6 day: 11 }
 }
diff --git a/third_party/outline-ss-server/linux/outline-ss-server b/third_party/outline-ss-server/linux/outline-ss-server
index 2ba7af20..276b80e3 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 3d37079e..4eeecf82 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