diff --git a/.drone.yml b/.drone.yml
index d8bdc9d1a6b..1878694a325 100644
--- a/.drone.yml
+++ b/.drone.yml
@@ -6139,7 +6139,7 @@ steps:
     "linux/amd64" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-amd64
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox:teleport15
-    --build-arg COMPILER_NAME=x86_64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=x86_64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=amd64 --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -6185,7 +6185,7 @@ steps:
     "linux/arm" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-arm
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox-arm:teleport15
-    --build-arg COMPILER_NAME=arm-linux-gnueabihf-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=arm-linux-gnueabihf-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=arm --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -6231,7 +6231,7 @@ steps:
     "linux/arm64" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-arm64
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox-arm:teleport15
-    --build-arg COMPILER_NAME=aarch64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=aarch64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=arm64 --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -8712,7 +8712,7 @@ steps:
     "linux/amd64" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-amd64
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox:teleport15
-    --build-arg COMPILER_NAME=x86_64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=x86_64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=amd64 --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -8758,7 +8758,7 @@ steps:
     "linux/arm" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-arm
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox-arm:teleport15
-    --build-arg COMPILER_NAME=arm-linux-gnueabihf-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=arm-linux-gnueabihf-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=arm --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -8804,7 +8804,7 @@ steps:
     "linux/arm64" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-arm64
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox-arm:teleport15
-    --build-arg COMPILER_NAME=aarch64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=aarch64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=arm64 --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -11285,7 +11285,7 @@ steps:
     "linux/amd64" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-amd64
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox:teleport15
-    --build-arg COMPILER_NAME=x86_64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=x86_64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=amd64 --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -11331,7 +11331,7 @@ steps:
     "linux/arm" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-arm
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox-arm:teleport15
-    --build-arg COMPILER_NAME=arm-linux-gnueabihf-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=arm-linux-gnueabihf-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=arm --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -11377,7 +11377,7 @@ steps:
     "linux/arm64" --tag drone-docker-registry:5000/teleport-operator:$(cat "/go/var/full-version")-arm64
     --file "/go/src/github.com/gravitational/teleport/integrations/operator/Dockerfile"
     --build-arg BUILDBOX=public.ecr.aws/gravitational/teleport-buildbox-arm:teleport15
-    --build-arg COMPILER_NAME=aarch64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.5
+    --build-arg COMPILER_NAME=aarch64-linux-gnu-gcc --build-arg GOLANG_VERSION=go1.21.6
     --build-arg PROTOC_VERSION=3.20.3 --build-arg TARGETARCH=arm64 --build-arg BUILD_ARCH=amd64
     /go/src/github.com/gravitational/teleport
   - docker logout "public.ecr.aws"
@@ -11976,6 +11976,6 @@ image_pull_secrets:
 - DOCKERHUB_CREDENTIALS
 ---
 kind: signature
-hmac: 759cdb197a5962b5bbd5f2e21bffb709d04429e28e18f07e0894d78d12073450
+hmac: 02f9a71d868451efb9fcfe9f56525912874113fb7a8b19ad8c682d37167550f3
 
 ...
diff --git a/build.assets/versions.mk b/build.assets/versions.mk
index 28bea757f0e..f472f6d3d5a 100644
--- a/build.assets/versions.mk
+++ b/build.assets/versions.mk
@@ -3,7 +3,7 @@
 # Keep versions in sync with devbox.json, when applicable.
 
 # Sync with devbox.json.
-GOLANG_VERSION ?= go1.21.5
+GOLANG_VERSION ?= go1.21.6
 
 NODE_VERSION ?= 18.18.2
 
diff --git a/go.mod b/go.mod
index d12d5d3c2ff..d8dc72e294d 100644
--- a/go.mod
+++ b/go.mod
@@ -2,7 +2,7 @@ module github.com/gravitational/teleport
 
 go 1.21
 
-toolchain go1.21.5
+toolchain go1.21.6
 
 require (
 	cloud.google.com/go/compute v1.23.3