diff --git a/rust/Cargo.lock b/rust/Cargo.lock
index f9c5a6472..3a7b044e4 100644
--- a/rust/Cargo.lock
+++ b/rust/Cargo.lock
@@ -3012,7 +3012,7 @@ dependencies = [
  "httpdate",
  "itoa 1.0.10",
  "pin-project-lite",
- "socket2 0.4.10",
+ "socket2 0.5.5",
  "tokio",
  "tower-service",
  "tracing",
@@ -8385,15 +8385,15 @@ dependencies = [
 
 [[package]]
 name = "wintun"
-version = "0.3.2"
+version = "0.4.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "29b83b0eca06dd125dbcd48a45327c708a6da8aada3d95a3f06db0ce4b17e0d4"
+checksum = "1b3c8c8876c686f8a2d6376999ac1c9a24c74d2968551c9394f7e89127783685"
 dependencies = [
  "c2rust-bitfields",
  "libloading 0.8.1",
  "log",
  "thiserror",
- "windows 0.51.1",
+ "windows 0.52.0",
 ]
 
 [[package]]
diff --git a/rust/connlib/shared/Cargo.toml b/rust/connlib/shared/Cargo.toml
index 343c49b23..25868c691 100644
--- a/rust/connlib/shared/Cargo.toml
+++ b/rust/connlib/shared/Cargo.toml
@@ -53,7 +53,7 @@ rtnetlink = { version = "0.13", default-features = false, features = ["tokio_soc
 
 # Windows tunnel dependencies
 [target.'cfg(target_os = "windows")'.dependencies]
-wintun = "0.3.2"
+wintun = "0.4.0"
 
 # Windows Win32 API
 [target.'cfg(windows)'.dependencies.windows]
diff --git a/rust/connlib/tunnel/Cargo.toml b/rust/connlib/tunnel/Cargo.toml
index 396a4595d..6059ae50b 100644
--- a/rust/connlib/tunnel/Cargo.toml
+++ b/rust/connlib/tunnel/Cargo.toml
@@ -53,7 +53,7 @@ tracing-android = "0.2"
 # Windows tunnel dependencies
 [target.'cfg(target_os = "windows")'.dependencies]
 uuid = { version = "1.5.0", features = ["v4"] }
-wintun = "0.3.2"
+wintun = "0.4.0"
 
 # Windows Win32 API
 [target.'cfg(windows)'.dependencies.windows]
diff --git a/rust/connlib/tunnel/src/device_channel/tun_windows.rs b/rust/connlib/tunnel/src/device_channel/tun_windows.rs
index 589c957ee..4ac8a0755 100644
--- a/rust/connlib/tunnel/src/device_channel/tun_windows.rs
+++ b/rust/connlib/tunnel/src/device_channel/tun_windows.rs
@@ -246,8 +246,7 @@ fn start_recv_thread(
                             break;
                         }
                     }
-                    // We get an Error::String when `Session::shutdown` is called
-                    Err(wintun::Error::String(_)) => break,
+                    Err(wintun::Error::ShuttingDown) => break,
                     Err(e) => {
                         tracing::error!("wintun::Session::receive_blocking: {e:#?}");
                         break;
diff --git a/rust/windows-client/src-tauri/Cargo.toml b/rust/windows-client/src-tauri/Cargo.toml
index add8a923e..f07f8a551 100755
--- a/rust/windows-client/src-tauri/Cargo.toml
+++ b/rust/windows-client/src-tauri/Cargo.toml
@@ -54,7 +54,7 @@ bincode = "1.3.3"
 tauri = { version = "1.5", features = [ "dialog", "notification", "shell-open-api", "system-tray" ] }
 tauri-utils = "1.5.1"
 winreg = "0.51.0"
-wintun = "0.3.2"
+wintun = "0.4.0"
 
 [target.'cfg(windows)'.dependencies.windows]
 version = "0.52.0"