diff --git a/.drone.yml b/.drone.yml
index a83997ea96601..a0e7de1c7d648 100644
--- a/.drone.yml
+++ b/.drone.yml
@@ -1006,8 +1006,8 @@ steps:
   - $Workspace = "$Env:WORKSPACE_DIR/$Env:DRONE_BUILD_NUMBER"
   - $TeleportSrc = "$Workspace/go/src/github.com/gravitational/teleport"
   - $OutputsDir = "$Workspace/outputs"
-  - $relcliUrl = 'https://cdn.teleport.dev/relcli-master-e148541-20230331T1403513-windows.exe'
-  - $relcliSha256 = '6e2ba2275d5d2bdd1c29def84d2de7d11149a9044c4fdca7c8d87c8e3fb8a91c'
+  - $relcliUrl = 'https://cdn.teleport.dev/relcli-master-93a9f40-20230504T2005101-windows.exe'
+  - $relcliSha256 = '22d32a57a4b999e619162bebb96d0adf4b3df2596ef4c89b77154e7f96abbf30'
   - . "$TeleportSrc/build.assets/windows/build.ps1"
   - Get-Relcli -Url $relcliUrl -Sha256 $relcliSha256 -Workspace $Workspace
   - Register-Artifacts -Workspace $Workspace -Outputs $OutputsDir
@@ -17106,6 +17106,6 @@ image_pull_secrets:
 - DOCKERHUB_CREDENTIALS
 ---
 kind: signature
-hmac: bcbaa90c991ef9730c11e1555ad687a896a3bde59cf8df4c296d019c0f4f51f5
+hmac: 6285c96c5277bc0aacb843eddff886b22b72c5f3761d96109b8b3562a7442e70
 
 ...
diff --git a/dronegen/windows.go b/dronegen/windows.go
index 838c9d2090ec1..5aa0100da71a3 100644
--- a/dronegen/windows.go
+++ b/dronegen/windows.go
@@ -23,8 +23,8 @@ const (
 	toolchainDir      = `/toolchains`
 	teleportSrc       = `/go/src/github.com/gravitational/teleport`
 
-	relcliURL    = `https://cdn.teleport.dev/relcli-master-e148541-20230331T1403513-windows.exe`
-	relcliSha256 = `6e2ba2275d5d2bdd1c29def84d2de7d11149a9044c4fdca7c8d87c8e3fb8a91c`
+	relcliURL    = `https://cdn.teleport.dev/relcli-master-93a9f40-20230504T2005101-windows.exe`
+	relcliSha256 = `22d32a57a4b999e619162bebb96d0adf4b3df2596ef4c89b77154e7f96abbf30`
 )
 
 func newWindowsPipeline(name string) pipeline {