diff --git a/Cargo.toml b/Cargo.toml
index 167a46a657ee..c64eaf6907a5 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -206,7 +206,7 @@ fs-set-times = "0.20.0"
 system-interface = { version = "0.26.0", features = ["cap_std_impls"] }
 io-lifetimes = { version = "2.0.2", default-features = false }
 io-extras = "0.18.0"
-rustix = "0.38.8"
+rustix = "0.38.21"
 is-terminal = "0.4.0"
 # wit-bindgen:
 wit-bindgen = { version = "0.13.0", default-features = false }
diff --git a/crates/test-programs/src/bin/preview2_udp_connect.rs b/crates/test-programs/src/bin/preview2_udp_connect.rs
new file mode 100644
index 000000000000..5100525e82ab
--- /dev/null
+++ b/crates/test-programs/src/bin/preview2_udp_connect.rs
@@ -0,0 +1,41 @@
+use test_programs::wasi::sockets::network::{
+    ErrorCode, IpAddress, IpAddressFamily, IpSocketAddress, Network,
+};
+use test_programs::wasi::sockets::udp::UdpSocket;
+
+fn test_udp_connect_disconnect_reconnect(net: &Network, family: IpAddressFamily) {
+    let unspecified_addr = IpSocketAddress::new(IpAddress::new_unspecified(family), 0);
+    let remote1 = IpSocketAddress::new(IpAddress::new_loopback(family), 4321);
+    let remote2 = IpSocketAddress::new(IpAddress::new_loopback(family), 4320);
+
+    let client = UdpSocket::new(family).unwrap();
+    client.blocking_bind(&net, unspecified_addr).unwrap();
+
+    _ = client.stream(None).unwrap();
+    assert_eq!(client.remote_address(), Err(ErrorCode::InvalidState));
+
+    _ = client.stream(None).unwrap();
+    assert_eq!(client.remote_address(), Err(ErrorCode::InvalidState));
+
+    _ = client.stream(Some(remote1)).unwrap();
+    assert_eq!(client.remote_address(), Ok(remote1));
+
+    _ = client.stream(Some(remote1)).unwrap();
+    assert_eq!(client.remote_address(), Ok(remote1));
+
+    _ = client.stream(Some(remote2)).unwrap();
+    assert_eq!(client.remote_address(), Ok(remote2));
+
+    _ = client.stream(None).unwrap();
+    assert_eq!(client.remote_address(), Err(ErrorCode::InvalidState));
+
+    _ = client.stream(Some(remote1)).unwrap();
+    assert_eq!(client.remote_address(), Ok(remote1));
+}
+
+fn main() {
+    let net = Network::default();
+
+    test_udp_connect_disconnect_reconnect(&net, IpAddressFamily::Ipv4);
+    test_udp_connect_disconnect_reconnect(&net, IpAddressFamily::Ipv6);
+}
diff --git a/crates/wasi/src/preview2/host/udp.rs b/crates/wasi/src/preview2/host/udp.rs
index a97bd1bcd187..e2d1e239fa6d 100644
--- a/crates/wasi/src/preview2/host/udp.rs
+++ b/crates/wasi/src/preview2/host/udp.rs
@@ -97,13 +97,19 @@ impl<T: WasiView> udp::HostUdpSocket for T {
             _ => return Err(ErrorCode::InvalidState.into()),
         }
 
+        // We disconnect & (re)connect in two distinct steps for two reasons:
+        // - To leave our socket instance in a consistent state in case the
+        //   connect fails.
+        // - When reconnecting to a different address, Linux sometimes fails
+        //   if there isn't a disconnect in between.
+
+        // Step #1: Disconnect
         if let UdpState::Connected = socket.udp_state {
-            // FIXME: Allow multiple (dis)connects. This needs to be supported by rustix first.
-            // rustix::net::disconnect(socket.udp_socket())?;
-            // socket.udp_state = UdpState::Bound;
-            return Err(ErrorCode::NotSupported.into());
+            disconnect(socket.udp_socket())?;
+            socket.udp_state = UdpState::Bound;
         }
 
+        // Step #2: (Re)connect
         if let Some(connect_addr) = remote_address {
             rustix::net::connect(socket.udp_socket(), &connect_addr)?;
             socket.udp_state = UdpState::Connected;
@@ -481,3 +487,12 @@ impl Subscribe for OutgoingDatagramStream {
         }
     }
 }
+
+fn disconnect<Fd: rustix::fd::AsFd>(sockfd: Fd) -> rustix::io::Result<()> {
+    match rustix::net::connect_unspec(sockfd) {
+        // BSD platforms return an error even if the socket was disconnected successfully.
+        #[cfg(target_os = "macos")]
+        Err(rustix::io::Errno::INVAL | rustix::io::Errno::AFNOSUPPORT) => Ok(()),
+        r => r,
+    }
+}
diff --git a/crates/wasi/tests/all/async_.rs b/crates/wasi/tests/all/async_.rs
index c1813476bf74..553e3846f220 100644
--- a/crates/wasi/tests/all/async_.rs
+++ b/crates/wasi/tests/all/async_.rs
@@ -319,6 +319,10 @@ async fn preview2_tcp_bind() {
     run(PREVIEW2_TCP_BIND_COMPONENT, false).await.unwrap()
 }
 #[test_log::test(tokio::test(flavor = "multi_thread"))]
+async fn preview2_udp_connect() {
+    run(PREVIEW2_UDP_CONNECT_COMPONENT, false).await.unwrap()
+}
+#[test_log::test(tokio::test(flavor = "multi_thread"))]
 async fn preview2_udp_sample_application() {
     run(PREVIEW2_UDP_SAMPLE_APPLICATION_COMPONENT, false)
         .await
diff --git a/crates/wasi/tests/all/sync.rs b/crates/wasi/tests/all/sync.rs
index 4347e01d904a..0e087ab8ced7 100644
--- a/crates/wasi/tests/all/sync.rs
+++ b/crates/wasi/tests/all/sync.rs
@@ -262,6 +262,10 @@ fn preview2_tcp_bind() {
     run(PREVIEW2_TCP_BIND_COMPONENT, false).unwrap()
 }
 #[test_log::test]
+fn preview2_udp_connect() {
+    run(PREVIEW2_UDP_CONNECT_COMPONENT, false).unwrap()
+}
+#[test_log::test]
 fn preview2_udp_sample_application() {
     run(PREVIEW2_UDP_SAMPLE_APPLICATION_COMPONENT, false).unwrap()
 }